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2 6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
2 6,7-dimethyl-8-ribityllumazine
riboflavin + 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidine-dione
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
6,7-dimethyl-8-[1'-(5'-deoxy-D-ribityl)]lumazine + 6,7-dimethyl-8-[1'-(5'-deoxy-D-ribityl)]lumazine
5'-deoxyriboflavin + ?
-
-
-
?
additional information
?
-
2 6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
2 6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
2 6,7-dimethyl-8-ribityllumazine
riboflavin + 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidine-dione
-
the reaction catalyzed by riboflavin synthase of Methanococcus jannaschii involves a pentacyclic intermediate, which is a diastereomer of the pentacyclic intermediate of riboflavin synthase of Escherichia coli
-
-
?
2 6,7-dimethyl-8-ribityllumazine
riboflavin + 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidine-dione
-
the reaction catalyzed by riboflavin synthase of Methanococcus jannaschii involves a pentacyclic intermediate, which is a diastereomer of the pentacyclic intermediate of riboflavin synthase of Escherichia coli
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
enzyme catalyzes the transfer of a four-carbon unit between 2 molecules of the substrate, 6,7-dimethyl-8-ribityllumazine
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
final step of biosynthesis of vitamin B2, i.e. riboflavin, the universal precursor of flavocoenzymes, overview
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
dismutation, exchange of a C4 fragment, regio- and stereospecific reaction
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
-
catalysed by the alpha-subunit, which forms a trimer surrounded by an icosahedral capsid of 60 beta subunits producing substrate 6,7-dimethyl-8-(1-D-ribityl)lumazine
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
-
-
-
r
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
dismutation
riboflavin binding site structure
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
final step of biosynthesis of vitamin B2, i.e. riboflavin, the universal precursor of flavocoenzymes, overview
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
ultimate step in the biosynthesis of riboflavin, i.e. vitamin B2, the precursor of flavin cofactors
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
dismutation, exchange of a C4 fragment, regio- and stereospecific reaction
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
mechanistical complex dismutation
-
-
r
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
mechanistically complex dismutation
-
-
r
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
final step of biosynthesis of vitamin B2, i.e. riboflavin, the universal precursor of flavocoenzymes, overview
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
ultimate step in the biosynthesis of riboflavin, pathway overview, evolution of vitamin B2 biosynthesis
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
dismutation, exchange of a C4 fragment, regio- and stereospecific reaction
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
transfer of a 4-carbon fragment
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
final step of biosynthesis of vitamin B2, i.e. riboflavin, the universal precursor of flavocoenzymes, overview
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
dismutation, exchange of a C4 fragment, regio- and stereospecific reaction
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
final step of biosynthesis of vitamin B2, i.e. riboflavin, the universal precursor of flavocoenzymes, overview
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
ultimate step in the biosynthesis of riboflavin, pathway overview
-
-
r
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
dismutation, exchange of a C4 fragment, regio- and stereospecific reaction
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
mechanistically complex dismutation
-
-
r
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
biosynthetic pathway
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
1 riboflavin is bound per monomer in a site at one end of the 6-stranded antiparallel beta-barrel which is comprised of elements of both monomers
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
Pseudomonas iodinum
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
i.e. 6,7-dimethyl-8-(1'-D-ribityl)lumazine
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
ir
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
additional information
?
-
-
vitamin B2 biosynthetic pathway evolution, hypothetical gene duplication conductive to the 2-domain architecture occurring very early in evolution
-
-
?
additional information
?
-
-
no activity with lumazine 5'-phosphate
-
-
?
additional information
?
-
-
beta-subunit of heavy riboflavin synthase catalyzes the formation of 6,7-dimethyl-8-ribityllumazine from 5-amino-6-ribitylamino-2,4-pyrimidinedione and a carbohydrate phosphate
-
-
?
additional information
?
-
-
dismutation of 6,7-dimethyl-8-ribityllumazine yielding riboflavin and 5-amino-6-ribitylamino-2,4-pyrimidinedione is catalyzed by the alpha-subunit
-
-
?
additional information
?
-
-
-
-
-
?
additional information
?
-
-
salvage cycle for the by-product of the reaction is involved in the de novo synthesis of riboflavin
-
-
?
additional information
?
-
-
overview
-
-
?
additional information
?
-
-
overview
-
-
?
additional information
?
-
-
-
-
-
?
additional information
?
-
-
no activity with lumazine 5'-phosphate
-
-
?
additional information
?
-
-
no activity with the dimeric pentacyclic reaction intermediate as substrate
-
-
?
additional information
?
-
-
utilization of the pentacyclic reaction intermediate as substrate
-
-
?
additional information
?
-
final step in the biosynthesis of riboflavin, the early steps in this pathway involve the addition of a nucleophile to the lumazine that will function as the donor of the four-carbon unit and the deprotonation of the C-7 methyl group of the lumazine that will function as the acceptor of the four-carbon unit to form the anion, although the identity of the nucleophile has not been rigorously established, likely candidates include water or one of the ribityl hydroxyl groups, nucleophilic addition of an anion to an imine affords an intermediate, which tautomerizes to yield a further intermediate, elimination of the anion results in an iminium ion which is attacked intramolecularly by the enamine to produce the pentacyclic intermediate, the pentacyclic compound has been isolated and shown to be a kinetically competent intermediate, 2 sequential elimination reactions then produce the final products
-
-
?
additional information
?
-
-
final step in the biosynthesis of riboflavin, the early steps in this pathway involve the addition of a nucleophile to the lumazine that will function as the donor of the four-carbon unit and the deprotonation of the C-7 methyl group of the lumazine that will function as the acceptor of the four-carbon unit to form the anion, although the identity of the nucleophile has not been rigorously established, likely candidates include water or one of the ribityl hydroxyl groups, nucleophilic addition of an anion to an imine affords an intermediate, which tautomerizes to yield a further intermediate, elimination of the anion results in an iminium ion which is attacked intramolecularly by the enamine to produce the pentacyclic intermediate, the pentacyclic compound has been isolated and shown to be a kinetically competent intermediate, 2 sequential elimination reactions then produce the final products
-
-
?
additional information
?
-
-
archaeal enzymes have diverged early in evolution from a common ancestor
-
-
?
additional information
?
-
-
active with the dimeric pentacyclic reaction intermediate as substrate
-
-
?
additional information
?
-
-
activity with different isotopomers, stereochemistry, overview
-
-
?
additional information
?
-
activity with different isotopomers, stereochemistry, overview
-
-
?
additional information
?
-
no activity with lumazine 5'-phosphate
-
-
?
additional information
?
-
-
no activity with lumazine 5'-phosphate
-
-
?
additional information
?
-
-
archaeal enzymes have diverged early in evolution from a common ancestor
-
-
?
additional information
?
-
no activity with lumazine 5'-phosphate
-
-
?
additional information
?
-
-
final step in the biosynthesis of riboflavin, the early steps in this pathway involve the addition of a nucleophile to the lumazine that will function as the donor of the four-carbon unit and the deprotonation of the C-7 methyl group of the lumazine that will function as the acceptor of the four-carbon unit to form the anion, although the identity of the nucleophile has not been rigorously established, likely candidates include water or one of the ribityl hydroxyl groups, nucleophilic addition of an anion to an imine affords an intermediate, which tautomerizes to yield a further intermediate, elimination of the anion results in an iminium ion which is attacked intramolecularly by the enamine to produce the pentacyclic intermediate, the pentacyclic compound has been isolated and shown to be a kinetically competent intermediate, 2 sequential elimination reactions then produce the final products
-
-
?
additional information
?
-
-
overview
-
-
?
additional information
?
-
structure-function relationship
-
-
?
additional information
?
-
-
structure-function relationship
-
-
?
additional information
?
-
substrate binding structure and catalytic mechanism by NMR analysis and protein perturbation studies using fluoro-substituted reaction intermediate analogues, i.e. 2 epimers of 6,7-bis(trifluoromethyl)-8-ribityllumazine hydrate, 6-trifluoromethyl-7-oxo-8-ribityllumazine, 6-carboxyethyl-7-oxo-8-ribityllumazine, and 5-nitro-6-ribitylamino-2,4-pyrimidinedione, overview
-
-
?
additional information
?
-
-
substrate binding structure and catalytic mechanism by NMR analysis and protein perturbation studies using fluoro-substituted reaction intermediate analogues, i.e. 2 epimers of 6,7-bis(trifluoromethyl)-8-ribityllumazine hydrate, 6-trifluoromethyl-7-oxo-8-ribityllumazine, 6-carboxyethyl-7-oxo-8-ribityllumazine, and 5-nitro-6-ribitylamino-2,4-pyrimidinedione, overview
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
2 6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
additional information
?
-
2 6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
2 6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
enzyme catalyzes the transfer of a four-carbon unit between 2 molecules of the substrate, 6,7-dimethyl-8-ribityllumazine
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
-
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
final step of biosynthesis of vitamin B2, i.e. riboflavin, the universal precursor of flavocoenzymes, overview
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
-
-
-
r
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
final step of biosynthesis of vitamin B2, i.e. riboflavin, the universal precursor of flavocoenzymes, overview
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
ultimate step in the biosynthesis of riboflavin, i.e. vitamin B2, the precursor of flavin cofactors
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
final step of biosynthesis of vitamin B2, i.e. riboflavin, the universal precursor of flavocoenzymes, overview
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
ultimate step in the biosynthesis of riboflavin, pathway overview, evolution of vitamin B2 biosynthesis
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
final step of biosynthesis of vitamin B2, i.e. riboflavin, the universal precursor of flavocoenzymes, overview
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
-
final step of biosynthesis of vitamin B2, i.e. riboflavin, the universal precursor of flavocoenzymes, overview
-
-
?
6,7-dimethyl-8-(1-D-ribityl)lumazine
riboflavin + 5-amino-6-ribitylamino-2,4-(1H,3H)-pyrimidinedione
ultimate step in the biosynthesis of riboflavin, pathway overview
-
-
r
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
biosynthetic pathway
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
Pseudomonas iodinum
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
i.e. 6,7-dimethyl-8-(1'-D-ribityl)lumazine
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
6,7-dimethyl-8-ribityllumazine + 6,7-dimethyl-8-ribityllumazine
riboflavin + 4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
-
-
-
-
?
additional information
?
-
-
vitamin B2 biosynthetic pathway evolution, hypothetical gene duplication conductive to the 2-domain architecture occurring very early in evolution
-
-
?
additional information
?
-
-
salvage cycle for the by-product of the reaction is involved in the de novo synthesis of riboflavin
-
-
?
additional information
?
-
final step in the biosynthesis of riboflavin, the early steps in this pathway involve the addition of a nucleophile to the lumazine that will function as the donor of the four-carbon unit and the deprotonation of the C-7 methyl group of the lumazine that will function as the acceptor of the four-carbon unit to form the anion, although the identity of the nucleophile has not been rigorously established, likely candidates include water or one of the ribityl hydroxyl groups, nucleophilic addition of an anion to an imine affords an intermediate, which tautomerizes to yield a further intermediate, elimination of the anion results in an iminium ion which is attacked intramolecularly by the enamine to produce the pentacyclic intermediate, the pentacyclic compound has been isolated and shown to be a kinetically competent intermediate, 2 sequential elimination reactions then produce the final products
-
-
?
additional information
?
-
-
final step in the biosynthesis of riboflavin, the early steps in this pathway involve the addition of a nucleophile to the lumazine that will function as the donor of the four-carbon unit and the deprotonation of the C-7 methyl group of the lumazine that will function as the acceptor of the four-carbon unit to form the anion, although the identity of the nucleophile has not been rigorously established, likely candidates include water or one of the ribityl hydroxyl groups, nucleophilic addition of an anion to an imine affords an intermediate, which tautomerizes to yield a further intermediate, elimination of the anion results in an iminium ion which is attacked intramolecularly by the enamine to produce the pentacyclic intermediate, the pentacyclic compound has been isolated and shown to be a kinetically competent intermediate, 2 sequential elimination reactions then produce the final products
-
-
?
additional information
?
-
-
archaeal enzymes have diverged early in evolution from a common ancestor
-
-
?
additional information
?
-
-
archaeal enzymes have diverged early in evolution from a common ancestor
-
-
?
additional information
?
-
-
final step in the biosynthesis of riboflavin, the early steps in this pathway involve the addition of a nucleophile to the lumazine that will function as the donor of the four-carbon unit and the deprotonation of the C-7 methyl group of the lumazine that will function as the acceptor of the four-carbon unit to form the anion, although the identity of the nucleophile has not been rigorously established, likely candidates include water or one of the ribityl hydroxyl groups, nucleophilic addition of an anion to an imine affords an intermediate, which tautomerizes to yield a further intermediate, elimination of the anion results in an iminium ion which is attacked intramolecularly by the enamine to produce the pentacyclic intermediate, the pentacyclic compound has been isolated and shown to be a kinetically competent intermediate, 2 sequential elimination reactions then produce the final products
-
-
?
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Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
(2-ethyl-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)methyl 3,4,5-triethoxybenzoate
-
-
(2E)-3-(2,3-dimethoxyphenyl)-N-[4-methyl-2-(4-methylpiperazin-1-yl)quinolin-6-yl]prop-2-enamide
-
-
1-deoxy-1-[2,6,8-trioxo-7-[4-(phosphonooxy)butyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol
2,4-dioxo-6-[(3S,4S,5R)-3,4,5,6-tetrahydroxyhexyl]-1,2,3,4-tetrahydropyrimidin-5-aminium chloride
2,4-dioxo-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]-1,2,3,4-tetrahydropyrimidin-5-aminium chloride
2-(4-ethoxyphenyl)-N-[3-(piperidin-1-yl)propyl]imidazo[2,1-b][1,3]benzothiazole-7-carboxamide
-
-
2-(4-methoxyphenyl)-N-[3-(piperidin-1-yl)propyl]imidazo[2,1-b][1,3]benzothiazole-7-carboxamide
-
-
2-Amino-4,6-dihydroxy-8-D-ribityl-7-pteridinone
-
-
2-chloro-N-(2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino)-1,2,3,4-tetrahydropyrimidin-5-yl)acetamide
2-chloro-N-(2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino)-1,2,3,4-tetrahydropyrimidin-5-yl)propanamide
2-[ethyl(methyl)amino]ethyl 4-[(5-ethyl-4-oxo-4,5-dihydrothieno[3,2-c]quinoline-2-carbonyl)amino]benzoate
-
-
4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]butanoic acid
-
comparison with inhibition of Bacillus subtilis lumazine synthase
4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]butyl dihydrogen phosphate
-
comparison with inhibition of Bacillus subtilis lumazine synthase
4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]propyl dihydrogen phosphate
-
competitive, comparison with inhibition of Bacillus subtilis lumazine synthase
5,5'-dithiobis(2-nitrobenzoate)
-
-
5,6,7,8-Tetrahydro-9-(1'-D-ribityl)isoalloxazine
-
-
5-(4-phosphonobutyryl)amino-6-D-ribitylaminouracil
-
comparison with inhibition of Bacillus subtilis luminazine synthase/riboflavin synthase
5-(4-phosphonopentyryl)amino-6-D-ribitylaminouracil
-
comparison with inhibition of Bacillus subtilis luminazine synthase/riboflavin synthase
5-(5-phosphonoxyvaleryl)amino-6-D-ribitylaminouracil
-
mixed inhibition, comparison with inhibition of Bacillus subtilis luminazine synthase/riboflavin synthase
5-(hexyl 6-dihydrogen phosphate)-6-([(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino)pyrimidine-2,4(1H,3H)-dione
5-(pentyl 6-dihydrogen phosphate)-6-([(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino)pyrimidine-2,4(1H,3H)-dione
-
comparison with inhibition of Bacillus subtilis lumazine synthase
5-amino-6-((2R,3R,4S)-2,3,4,5-tetrahydroxypentyloxy)-pyrimidine-2,4(1H,3H)-dione
5-amino-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
5-nitro-6-[(3S,4S,5R)-3,4,5,6-tetrahydroxyhexyl]pyrimidine-2,4(1H,3H)-dione
5-nitro-6-[[(2R,3R,4R)-2,3,4,5 tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
5-nitro-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
5-nitro-6-[[(2S,3R,4R)-2,3,4,5-tetrahydroxypentyl]oxy]pyrimidine-2,4(1H,3H)-dione
5-nitro-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]pyrimidine-2,4(1H,3H)-dione
5-[3-(propan-2-yl)-1H-pyrazol-5-yl]-3-(3,4,5-trimethoxyphenyl)-1,2,4-oxadiazole
-
-
6,7-dihydroxy-8-ribityllumazine
-
-
6,7-dimethyl-8-(1'-D-xylityl)lumazine
-
-
6-Methyl-7-hydroxy-8-ribityllumazine
6-methyl-7-methylidene-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,8-dihydropyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione
-
competitive, comparison with inhibition of Bacillus subtilis lumazine synthase
7-hydroxy-6-(2-carboxyethyl)-8-(1-D-ribityl)lumazine
-
-
7-hydroxy-6-(D-1,2-dihydroxyethyl)-8-(1-D-ribityl)lumazine
-
-
7-Hydroxy-6-(L-1,2-dihydroxyethyl)-8-(1-D-ribityl)lumazine
-
i.e. photolumazine A
7-hydroxy-6-(p-hydroxyphenyl)-8-(1-D-ribityl)lumazine
-
-
7-Hydroxy-6-hydroxymethyl-8-(1-D-ribityl)lumazine
-
photolumazine B
7-hydroxy-7-methyl-8-((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)-7,8-dihydropteridin-2,4,6(1H,3H,5H)-trione
7-Hydroxy-8-(1-D-ribityl)lumazine
-
i.e. photolumazine
8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-5,8-dihydropteridine-2,4,6,7(1H,3H)-tetrone
9-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,9-dihydro-1H-purine-2,6,8(3H)-trione
Avidin
-
moderately, no prevention by biotin
-
ethyl 2-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-ylamino)-2-oxoacetate
ethyl 5-(diethylcarbamoyl)-2-[2-(4-methoxyphenoxy)acetamido]-4-methylthiophene-3-carboxylate
-
-
ethyl [(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)amino](oxo)acetate
ethyl [(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)amino](oxo)acetate
methyl 2-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-ylamino)-2-oxoacetate
N-(2,4-dioxo-6-((2R,3R,4R)-2,3,4,5-tetrahydroxypentylthio)-1,2,3,4-tetrahydropyrimidin-5-yl)methacrylamide
N-(2,4-dioxo-6-((2R,3R,4R)-2,3,4,5-tetrahydroxypentylthio)-1,2,3,4-tetrahydropyrimidin-5-yl)propionamide
N-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-yl)isobutyramide
N-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-yl)methacrylamide
N-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-yl)propionamide
N-(2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino)-1,2,3,4-tetrahydropyrimidin-5-yl)-3,3,3-trifluoropropanamide
N-(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)-2-methylpropanamide
N-(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)propanamide
N-(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-methacrylamide
N-(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)propanamide
N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dion-5-ylpropionamide
-
uncompetitive
N-6-(ribitylamino)pyrimidine-2,4(1H,3H)-dione-5-ylisobutyramide
-
uncompetitive
N-[2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino]-1,2,3,4-tetrahydropyrimidin-5-yl)methacrylamide
N-[2,4-dioxo-6-(ribitylamino)-1,2,3,4-tetrahydropyrimidin-5-yl]oxalamic acid ethyl ester
-
mixed type inhibition
N-[3-(azepan-1-yl)propyl]-2-(4-methoxyphenyl)imidazo[2,1-b][1,3]benzothiazole-7-carboxamide
-
-
N-[3-(diethylamino)propyl]-2-(4-ethoxyphenyl)imidazo[2,1-b][1,3]benzothiazole-7-carboxamide
-
-
N-[3-(diethylamino)propyl]-2-(4-methylphenyl)imidazo[2,1-b][1,3]benzothiazole-7-carboxamide
-
-
p-chloromercuribenzenesulfonate
-
reversible by cysteine or 2-mercaptoethanol
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](m-tolyl)methanone
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](o-tolyl)methanone
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](p-tolyl)methanone
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](m-tolyl)methanone
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](o-tolyl)methanone
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](p-tolyl)methanone
1-deoxy-1-[2,6,8-trioxo-7-[4-(phosphonooxy)butyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol
-
competitive inhibition
1-deoxy-1-[2,6,8-trioxo-7-[4-(phosphonooxy)butyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol
-
competitive inhibition
2,4-dioxo-6-[(3S,4S,5R)-3,4,5,6-tetrahydroxyhexyl]-1,2,3,4-tetrahydropyrimidin-5-aminium chloride
-
uncompetitive inhibition
2,4-dioxo-6-[(3S,4S,5R)-3,4,5,6-tetrahydroxyhexyl]-1,2,3,4-tetrahydropyrimidin-5-aminium chloride
-
uncompetitive inhibition
2,4-dioxo-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]-1,2,3,4-tetrahydropyrimidin-5-aminium chloride
-
-
2,4-dioxo-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]-1,2,3,4-tetrahydropyrimidin-5-aminium chloride
-
-
2-chloro-N-(2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino)-1,2,3,4-tetrahydropyrimidin-5-yl)acetamide
-
-
2-chloro-N-(2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino)-1,2,3,4-tetrahydropyrimidin-5-yl)acetamide
-
uncompetitive inhibition
2-chloro-N-(2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino)-1,2,3,4-tetrahydropyrimidin-5-yl)propanamide
-
-
2-chloro-N-(2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino)-1,2,3,4-tetrahydropyrimidin-5-yl)propanamide
-
competitive inhibition
5-(hexyl 6-dihydrogen phosphate)-6-([(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino)pyrimidine-2,4(1H,3H)-dione
-
comparison with inhibition of Bacillus subtilis lumazine synthase
5-(hexyl 6-dihydrogen phosphate)-6-([(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino)pyrimidine-2,4(1H,3H)-dione
-
mixed inhibition, comparison with inhibition of Bacillus subtilis luminazine synthase/riboflavin synthase
5-amino-6-((2R,3R,4S)-2,3,4,5-tetrahydroxypentyloxy)-pyrimidine-2,4(1H,3H)-dione
-
uncompetitive inhibition
5-amino-6-((2R,3R,4S)-2,3,4,5-tetrahydroxypentyloxy)-pyrimidine-2,4(1H,3H)-dione
-
uncompetitive inhibition
5-amino-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
-
partial inhibition
5-amino-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
-
competitive inhibition
5-nitro-6-[(3S,4S,5R)-3,4,5,6-tetrahydroxyhexyl]pyrimidine-2,4(1H,3H)-dione
-
partial inhibition
5-nitro-6-[(3S,4S,5R)-3,4,5,6-tetrahydroxyhexyl]pyrimidine-2,4(1H,3H)-dione
-
competitive inhibition
5-nitro-6-[[(2R,3R,4R)-2,3,4,5 tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
-
-
5-nitro-6-[[(2R,3R,4R)-2,3,4,5 tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
-
-
5-nitro-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
-
partial inhibition
5-nitro-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
-
partial inhibition
5-nitro-6-[[(2S,3R,4R)-2,3,4,5-tetrahydroxypentyl]oxy]pyrimidine-2,4(1H,3H)-dione
-
competitive inhibition
5-nitro-6-[[(2S,3R,4R)-2,3,4,5-tetrahydroxypentyl]oxy]pyrimidine-2,4(1H,3H)-dione
-
partial inhibition
5-nitro-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]pyrimidine-2,4(1H,3H)-dione
-
mixed-type inhibition
5-nitro-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]pyrimidine-2,4(1H,3H)-dione
-
competitive inhibition
6-Methyl-7-hydroxy-8-ribityllumazine
-
-
6-Methyl-7-hydroxy-8-ribityllumazine
-
-
6-Methyl-7-hydroxy-8-ribityllumazine
-
-
7-hydroxy-7-methyl-8-((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)-7,8-dihydropteridin-2,4,6(1H,3H,5H)-trione
-
-
7-hydroxy-7-methyl-8-((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)-7,8-dihydropteridin-2,4,6(1H,3H,5H)-trione
-
competitive inhibition
8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-5,8-dihydropteridine-2,4,6,7(1H,3H)-tetrone
-
competitive inhibition
8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-5,8-dihydropteridine-2,4,6,7(1H,3H)-tetrone
-
-
9-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,9-dihydro-1H-purine-2,6,8(3H)-trione
-
competitive, comparison with inhibition of Bacillus subtilis lumazine synthase
9-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,9-dihydro-1H-purine-2,6,8(3H)-trione
-
competitive inhibition
9-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,9-dihydro-1H-purine-2,6,8(3H)-trione
-
-
Cu2+
-
-
ethyl 2-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-ylamino)-2-oxoacetate
-
uncompetitive inhibition
ethyl 2-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-ylamino)-2-oxoacetate
-
uncompetitive inhibition
ethyl [(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)amino](oxo)acetate
-
mixed-type inhibition
ethyl [(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)amino](oxo)acetate
-
-
ethyl [(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)amino](oxo)acetate
-
-
ethyl [(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)amino](oxo)acetate
-
uncompetitive inhibition
Hg2+
-
-
methyl 2-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-ylamino)-2-oxoacetate
-
uncompetitive inhibition
methyl 2-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-ylamino)-2-oxoacetate
-
uncompetitive inhibition
N-(2,4-dioxo-6-((2R,3R,4R)-2,3,4,5-tetrahydroxypentylthio)-1,2,3,4-tetrahydropyrimidin-5-yl)methacrylamide
-
-
N-(2,4-dioxo-6-((2R,3R,4R)-2,3,4,5-tetrahydroxypentylthio)-1,2,3,4-tetrahydropyrimidin-5-yl)methacrylamide
-
uncompetitive inhibition
N-(2,4-dioxo-6-((2R,3R,4R)-2,3,4,5-tetrahydroxypentylthio)-1,2,3,4-tetrahydropyrimidin-5-yl)propionamide
-
-
N-(2,4-dioxo-6-((2R,3R,4R)-2,3,4,5-tetrahydroxypentylthio)-1,2,3,4-tetrahydropyrimidin-5-yl)propionamide
-
uncompetitive inhibition
N-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-yl)isobutyramide
-
-
N-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-yl)isobutyramide
-
uncompetitive inhibition
N-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-yl)methacrylamide
-
-
N-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-yl)methacrylamide
-
uncompetitive inhibition
N-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-yl)propionamide
-
-
N-(2,4-dioxo-6-((2S,3R,4R)-2,3,4,5-tetrahydroxypentyloxy)-1,2,3,4-tetrahydropyrimidin-5-yl)propionamide
-
uncompetitive inhibition
N-(2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino)-1,2,3,4-tetrahydropyrimidin-5-yl)-3,3,3-trifluoropropanamide
-
-
N-(2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino)-1,2,3,4-tetrahydropyrimidin-5-yl)-3,3,3-trifluoropropanamide
-
uncompetitive inhibition
N-(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)-2-methylpropanamide
-
uncompetitive inhibition
N-(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)-2-methylpropanamide
-
-
N-(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)propanamide
-
uncompetitive inhibition
N-(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)propanamide
-
-
N-(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-methacrylamide
-
-
N-(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-methacrylamide
-
uncompetitive inhibition
N-(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)propanamide
-
-
N-(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)propanamide
-
uncompetitive inhibition
N-[2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino]-1,2,3,4-tetrahydropyrimidin-5-yl)methacrylamide
-
-
N-[2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino]-1,2,3,4-tetrahydropyrimidin-5-yl)methacrylamide
-
partial inhibition
p-chloromercuribenzoate
-
-
p-chloromercuribenzoate
-
-
p-chloromercuribenzoate
-
-
riboflavin
-
sigmoidal product inhibition
riboflavin
-
product inhibition, Saccharomyces cerevisiae
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](m-tolyl)methanone
covalent hydrate of trifluoromethylated pyrazole
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](m-tolyl)methanone
-
covalent hydrate of trifluoromethylated pyrazole
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](o-tolyl)methanone
covalent hydrate of trifluoromethylated pyrazole
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](o-tolyl)methanone
-
covalent hydrate of trifluoromethylated pyrazole
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](p-tolyl)methanone
covalent hydrate of trifluoromethylated pyrazole
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](p-tolyl)methanone
-
covalent hydrate of trifluoromethylated pyrazole
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](m-tolyl)methanone
covalent hydrate of trifluoromethylated pyrazole
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](m-tolyl)methanone
-
covalent hydrate of trifluoromethylated pyrazole
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](o-tolyl)methanone
covalent hydrate of trifluoromethylated pyrazole
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](o-tolyl)methanone
-
covalent hydrate of trifluoromethylated pyrazole
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](p-tolyl)methanone
covalent hydrate of trifluoromethylated pyrazole
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](p-tolyl)methanone
-
covalent hydrate of trifluoromethylated pyrazole
additional information
-
a high-throughput screening for inhibitors of riboflavin synthase identifies antimicrobial compounds to treat brucellosis
-
additional information
-
incorporation of an amide into 5-phosphonoalkyl-6-D-ribitylaminopyrimidinedione lumazine synthase inhibitors results in an unexpected reversal of selectivity for riboflavin synthase versus lumazine synthase
-
additional information
-
no effect by Ba2+, Co2+, EDTA
-
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0.332
1-deoxy-1-[2,6,8-trioxo-7-[4-(phosphonooxy)butyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl]-D-ribitol
-
in 100 mM Tris-HCl, pH 7.0, 100 mM NaCl, 2% (v/v) DMSO, 5 mM dithiothreitol, at 27°C
0.0025 - 0.047
2,4-dioxo-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]-1,2,3,4-tetrahydropyrimidin-5-aminium chloride
0.314
2-chloro-N-(2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino)-1,2,3,4-tetrahydropyrimidin-5-yl)propanamide
-
in 100 mM Tris-HCl, pH 7.0, 100 mM NaCl, 2% (v/v) DMSO, 5 mM dithiothreitol, at 27°C
0.02
4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]butanoic acid
-
pH 7.5, 37°C
0.15
4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]butyl dihydrogen phosphate
-
pH 7.5, 37°C
1.6
4-[2,4,7-trioxo-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1,2,3,4,7,8-hexahydropteridin-6-yl]propyl dihydrogen phosphate
-
pH 7.5, 37°C
0.16
5-(4-phosphonobutyryl)amino-6-D-ribitylaminouracil
-
pH 7.5, 37°C
0.0068
5-(4-phosphonopentyryl)amino-6-D-ribitylaminouracil
-
pH 7.5, 37°C
0.19
5-(5-phosphonoxyvaleryl)amino-6-D-ribitylaminouracil
-
pH 7.5, 37°C
1
5-(hexyl 6-dihydrogen phosphate)-6-([(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino)pyrimidine-2,4(1H,3H)-dione
-
pH 7.5, 37°C
1
5-(pentyl 6-dihydrogen phosphate)-6-([(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino)pyrimidine-2,4(1H,3H)-dione
-
pH 7.5, 37°C
0.0025 - 0.047
5-amino-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
0.0084 - 0.037
5-nitro-6-[(3S,4S,5R)-3,4,5,6-tetrahydroxyhexyl]pyrimidine-2,4(1H,3H)-dione
0.00056 - 0.0027
5-nitro-6-[[(2R,3R,4R)-2,3,4,5 tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
0.00056 - 0.0027
5-nitro-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
0.036 - 0.038
5-nitro-6-[[(2S,3R,4R)-2,3,4,5-tetrahydroxypentyl]oxy]pyrimidine-2,4(1H,3H)-dione
0.0042 - 0.008
5-nitro-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]pyrimidine-2,4(1H,3H)-dione
0.0029 - 0.18
6-Methyl-7-hydroxy-8-ribityllumazine
0.65
6-methyl-7-methylidene-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,8-dihydropyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione
-
pH 7.5, 37°C
0.027
7-hydroxy-6-(2-carboxyethyl)-8-(1-D-ribityl)lumazine
-
-
0.017
7-hydroxy-6-(D-1,2-dihydroxyethyl)-8-(1-D-ribityl)lumazine
-
-
0.017
7-Hydroxy-6-(L-1,2-dihydroxyethyl)-8-(1-D-ribityl)lumazine
-
-
0.028
7-hydroxy-6-(p-hydroxyphenyl)-8-(1-D-ribityl)lumazine
-
-
0.003
7-Hydroxy-6-hydroxymethyl-8-(1-D-ribityl)lumazine
-
-
0.00074
7-hydroxy-7-methyl-8-((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)-7,8-dihydropteridin-2,4,6(1H,3H,5H)-trione
-
in 100 mM Tris-HCl, pH 7.0, 100 mM NaCl, 2% (v/v) DMSO, 5 mM dithiothreitol, at 27°C
0.011
7-Hydroxy-8-(1-D-ribityl)lumazine
-
-
0.0000062
8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-5,8-dihydropteridine-2,4,6,7(1H,3H)-tetrone
-
in 100 mM Tris-HCl, pH 7.0, 100 mM NaCl, 2% (v/v) DMSO, 5 mM dithiothreitol, at 27°C
0.00061
9-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,9-dihydro-1H-purine-2,6,8(3H)-trione
0.0000013
ethyl [(2,4-dioxo-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]-1,2,3,4-tetrahydropyrimidin-5-yl)amino](oxo)acetate
-
in 100 mM Tris-HCl, pH 7.0, 100 mM NaCl, 2% (v/v) DMSO, 5 mM dithiothreitol, at 27°C
0.052
N-[2,4-dioxo-6-((2S,3S,4R)-2,3,4,5-tetrahydroxypentylamino]-1,2,3,4-tetrahydropyrimidin-5-yl)methacrylamide
-
in 100 mM Tris-HCl, pH 7.0, 100 mM NaCl, 2% (v/v) DMSO, 5 mM dithiothreitol, at 27°C
0.014 - 0.106
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](m-tolyl)methanone
0.0087 - 0.036
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](o-tolyl)methanone
0.01 - 0.135
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](p-tolyl)methanone
0.02 - 0.05
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](m-tolyl)methanone
0.0067 - 0.312
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](o-tolyl)methanone
0.01 - 0.104
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](p-tolyl)methanone
additional information
additional information
-
inhibition kinetics, recombinant enzyme
-
0.0025
2,4-dioxo-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]-1,2,3,4-tetrahydropyrimidin-5-aminium chloride
-
pH 7.0, 27°C
0.047
2,4-dioxo-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]-1,2,3,4-tetrahydropyrimidin-5-aminium chloride
-
pH 7.0, 27°C
0.0025
5-amino-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
-
in 100 mM Tris-HCl, pH 7.0, 100 mM NaCl, 2% (v/v) DMSO, 5 mM dithiothreitol, at 27°C
0.047
5-amino-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
-
in 100 mM Tris-HCl, pH 7.0, 100 mM NaCl, 2% (v/v) DMSO, 5 mM dithiothreitol, at 27°C
0.0084
5-nitro-6-[(3S,4S,5R)-3,4,5,6-tetrahydroxyhexyl]pyrimidine-2,4(1H,3H)-dione
-
in 100 mM Tris-HCl, pH 7.0, 100 mM NaCl, 2% (v/v) DMSO, 5 mM dithiothreitol, at 27°C
0.037
5-nitro-6-[(3S,4S,5R)-3,4,5,6-tetrahydroxyhexyl]pyrimidine-2,4(1H,3H)-dione
-
in 100 mM Tris-HCl, pH 7.0, 100 mM NaCl, 2% (v/v) DMSO, 5 mM dithiothreitol, at 27°C
0.00056
5-nitro-6-[[(2R,3R,4R)-2,3,4,5 tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
-
pH 7.0, 27°C
0.0027
5-nitro-6-[[(2R,3R,4R)-2,3,4,5 tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
-
pH 7.0, 27°C
0.00056
5-nitro-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
-
in 100 mM Tris-HCl, pH 7.0, 100 mM NaCl, 2% (v/v) DMSO, 5 mM dithiothreitol, at 27°C
0.0027
5-nitro-6-[[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl]pyrimidine-2,4(1H,3H)-dione
-
in 100 mM Tris-HCl, pH 7.0, 100 mM NaCl, 2% (v/v) DMSO, 5 mM dithiothreitol, at 27°C
0.036
5-nitro-6-[[(2S,3R,4R)-2,3,4,5-tetrahydroxypentyl]oxy]pyrimidine-2,4(1H,3H)-dione
-
in 100 mM Tris-HCl, pH 7.0, 100 mM NaCl, 2% (v/v) DMSO, 5 mM dithiothreitol, at 27°C
0.038
5-nitro-6-[[(2S,3R,4R)-2,3,4,5-tetrahydroxypentyl]oxy]pyrimidine-2,4(1H,3H)-dione
-
in 100 mM Tris-HCl, pH 7.0, 100 mM NaCl, 2% (v/v) DMSO, 5 mM dithiothreitol, at 27°C
0.0042
5-nitro-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]pyrimidine-2,4(1H,3H)-dione
-
in 100 mM Tris-HCl, pH 7.0, 100 mM NaCl, 2% (v/v) DMSO, 5 mM dithiothreitol, at 27°C
0.008
5-nitro-6-[[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]pyrimidine-2,4(1H,3H)-dione
-
in 100 mM Tris-HCl, pH 7.0, 100 mM NaCl, 2% (v/v) DMSO, 5 mM dithiothreitol, at 27°C
0.0029
6-Methyl-7-hydroxy-8-ribityllumazine
-
-
0.18
6-Methyl-7-hydroxy-8-ribityllumazine
-
-
0.00061
9-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,9-dihydro-1H-purine-2,6,8(3H)-trione
-
pH 7.5, 37°C
0.00061
9-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-7,9-dihydro-1H-purine-2,6,8(3H)-trione
-
in 100 mM Tris-HCl, pH 7.0, 100 mM NaCl, 2% (v/v) DMSO, 5 mM dithiothreitol, at 27°C
0.014
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](m-tolyl)methanone
-
Ki value, mechanism is partial
0.038
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](m-tolyl)methanone
-
Kis value, mechanism is partial
0.091
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](m-tolyl)methanone
Kis value, mechanism is partial
0.106
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](m-tolyl)methanone
Ki value, mechanism is partial
0.0087
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](o-tolyl)methanone
-
noncompetitive mechanism, compound has a kis value of 0.0087 mM and moderate antibiotic activity against both Mycobacterium tuberculosis replicating phenotype and non-replicating persistent phenotype
0.031
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](o-tolyl)methanone
partial mechanism, Ki value
0.036
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](o-tolyl)methanone
partial mechanism, Kis value
0.01
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](p-tolyl)methanone
-
Kis value, mechanism is partial
0.016
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](p-tolyl)methanone
-
Ki value, mechanism is partial
0.135
[3-(4-chlorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](p-tolyl)methanone
Ki value, mechanism is competitive
0.02
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](m-tolyl)methanone
partial mechanism, Kis value
0.0366
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](m-tolyl)methanone
-
noncompetitive mechanism, the most potent antibiotic compound displays a minimum inhibitory concentration of 0.0366 mM versus Mycobacterium tuberculosis replicating phenotype, the compound and its analogues provide the first examples of riboflavin synthase inhibitors with antibiotic activity
0.0489
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](m-tolyl)methanone
-
noncompetitive mechanism, the most potent antibiotic compound displays a minimum inhibitory concentration of 0.0489 mM versus Mycobacterium tuberculosis nonreplicating phenotype
0.05
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](m-tolyl)methanone
partial mechanism, Ki value
0.0067
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](o-tolyl)methanone
-
Ki value, mechanism is partial
0.016
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](o-tolyl)methanone
-
Kis value, mechanism is partial
0.057
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](o-tolyl)methanone
Kis value, mechanism is partial
0.312
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](o-tolyl)methanone
Ki value, mechanism is partial
0.01
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](p-tolyl)methanone
-
Kis value, mechanism is partial
0.023
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](p-tolyl)methanone
-
Ki value, mechanism is partial
0.061
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](p-tolyl)methanone
Ki value, mechanism is partial
0.104
[5-(4-chlorophenyl)-5-hydroxy-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl](p-tolyl)methanone
Kis value, mechanism is partial
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Crystal structure of riboflavin synthase
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Escherichia coli, no activity in Homo sapiens
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Studies on the reaction mechanism of riboflavin synthase: X-ray crystal structure of a complex with 6-carboxyethyl-7-oxo-8-ribityllumazine
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Schizosaccharomyces pombe (Q9Y7P0), Schizosaccharomyces pombe
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Design, synthesis, and evaluation of 6-carboxyalkyl and 6-phosphonoxyalkyl derivatives of 7-oxo-8-ribitylaminolumazines as inhibitors of riboflavin synthase and lumazine synthase
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A new series of N-[2,4-dioxo-6-d-ribitylamino-1,2,3,4-tetrahydropyrimidin-5-yl]oxalamic acid derivatives as inhibitors of lumazine synthase and riboflavin synthase: design, synthesis, biochemical evaluation, crystallography, and mechanistic implications
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Escherichia coli
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Discovery and development of the covalent hydrates of trifluoromethylated pyrazoles as riboflavin synthase inhibitors with antibiotic activity against Mycobacterium tuberculosis
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Escherichia coli, Mycobacterium tuberculosis
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47
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Escherichia coli
-
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58
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280
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281
1224-1232
2006
Methanocaldococcus jannaschii (Q58584), Methanocaldococcus jannaschii, Methanocaldococcus jannaschii DSM 2661 (Q58584)
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Serer, M.I.; Bonomi, H.R.; Guimaraes, B.G.; Rossi, R.C.; Goldbaum, F.A.; Klinke, S.
Crystallographic and kinetic study of riboflavin synthase from Brucella abortus, a chemotherapeutic target with an enhanced intrinsic flexibility
Acta Crystallogr. Sect. D
70
1419-1434
2014
Brucella abortus (Q2YN92), Brucella abortus, Brucella abortus 2308 (Q2YN92)
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Zhao, Y.; Wang, D.; Wu, T.; Guo, A.; Dong, H.; Zhang, C.
Transgenic expression of a rice riboflavin synthase gene in tobacco enhances plant growth and resistance to Tobacco mosaic virus
Can. J. Plant Pathol.
36
100-109
2014
Oryza sativa
-
brenda
Ladenstein, R.; Fischer, M.; Bacher, A.
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