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BRENDA support

Ligand D-fructofuranose

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Basic Ligand Information

Molecular Structure
Picture of D-fructofuranose (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
Molfile
C6H12O6
D-fructofuranose
RFSUNEUAIZKAJO-VRPWFDPXSA-N
 Download
Synonyms:
arabino-hexulose, D-(-)-fructose, D-(-)-Levulose, D-(-)fructose, D-fructose, D-fructose[side 2], fructose, Fruit sugar, levulose

Related pathways

Pathway Source
Pathways
BRENDA
degradation of sugar alcohols, metabolism of disaccharids, non-pathway related
KEGG
ABC transporters, Amino sugar and nucleotide sugar metabolism, Biosynthesis of nucleotide sugars, Biosynthesis of secondary metabolites, Carbohydrate digestion and absorption more
MetaCyc
D-sorbitol degradation I, fructan degradation, heterolactic fermentation, inulin degradation, mannitol cycle more


Show all pahtways known for Show all BRENDA pathways known for D-fructofuranose

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (32 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
fructose + NADPH = sorbitol + NADP+
show the reaction diagram
-
D-fructose + NADP+ = 5-dehydro-D-fructose + NADPH
show the reaction diagram
-
D-fructose + NADPH = D-mannitol + NADP+
show the reaction diagram
-
D-fructose + NADPH + H+ = sorbitol + NADP+
show the reaction diagram
-
D-fructose + NADH + H+ = D-mannitol + NAD+
show the reaction diagram
-
D-fructose + ferricenium ion = ? + ferrocene
show the reaction diagram
-
ATP + D-fructose = ADP + D-fructose 1-phosphate
show the reaction diagram
-
ATP + D-fructose = ADP + D-fructose 6-phosphate
show the reaction diagram
-
D-fructose + H2O = ?
show the reaction diagram
-
D-fructose = D-psicose
show the reaction diagram
-
D-fructose = D-psicose
show the reaction diagram
-
D-fructose = D-psicose
show the reaction diagram
-
D-fructose = D-mannose
show the reaction diagram
-
D-fructose = D-mannose
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (66 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
D-sorbitol + NAD+ = D-fructose + NADH + H+
show the reaction diagram
-
-
sorbitol + NAD+ = D-fructose + NADH
show the reaction diagram
-
sorbitol + NAD+ = D-fructose + NADH + H+
show the reaction diagram
-
-
D-mannitol + NAD+ = D-fructose + NADH + H+
show the reaction diagram
-
-
D-mannitol + ferricytochrome c = D-fructose + ferrocytochrome c
show the reaction diagram
-
D-glucitol + NAD+ = D-fructose + NADH + H+
show the reaction diagram
-
-
sucrose + (1->6)-alpha-D-glucan = D-fructose + (1->6)-alpha-D-glucan containing a (1->3)-alpha-D-glucose branch
show the reaction diagram
-
-
sucrose = highly branched soluble glucan + D-fructose + ?
show the reaction diagram
-
-
sucrose + (1->6)-alpha-D-glucan = D-fructose + (1->6)-alpha-D-glucan containing a (1->2)-alpha-D-glucose branch
show the reaction diagram
-
-
D-fructose 1-phosphate + H2O = D-fructose + phosphate
show the reaction diagram
-
-
fructan + H2O = D-fructose + ?
show the reaction diagram
-
-
palatinose + H2O = alpha-D-glucopyranose + D-fructofuranose
show the reaction diagram
-
-
lactulose + H2O = D-fructose + D-galactose
show the reaction diagram
-
-
4-O-beta-D-galactopyranosyl-D-fructoside + H2O = beta-D-galactose + D-fructose
show the reaction diagram
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levan + H2O = fructose + beta-1,2-oligofructans
show the reaction diagram
-
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inulin + H2O = D-fructose + fructooligosaccharides
show the reaction diagram
-
-
fructans + H2O = D-fructose
show the reaction diagram
-
-
sucrose 6-phosphate + H2O = D-glucose 6-phosphate + D-fructose
show the reaction diagram
-
-
D-psicose = D-fructose
show the reaction diagram
-
-
D-psicose = D-fructose
show the reaction diagram
-
-
D-psicose = D-fructose
show the reaction diagram
-
-
D-Mannose = D-Fructose
show the reaction diagram
-
-
D-Glucose = D-Fructose
show the reaction diagram
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D-Mannose = D-Fructose
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (173 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
D-fructose + NADPH + H+ = ? + NADP+
show the reaction diagram
-
D-fructose + NADH + H+ = D-mannitol + NAD+
show the reaction diagram
-
D-fructose + NADH + H+ = D-sorbitol + NAD+
show the reaction diagram
-
fructose + NADPH = sorbitol + NADP+
show the reaction diagram
-
D-fructose + NADPH = ? + NADP+
show the reaction diagram
-
D-fructose + NAD(P)H + H+ = D-arabino-hexitol + NAD(P)+
show the reaction diagram
-
D-fructose + NADPH = D-mannitol + NADP+
show the reaction diagram
-
D-fructose + NADPH + H+ = sorbitol + NADP+
show the reaction diagram
-
D-fructose + NADPH = 5-dehydro-D-fructose + NADP+
show the reaction diagram
-
D-fructose + O2 = ?
show the reaction diagram
-
D-fructose + 2,6-dichloroindophenol = ? + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
fructose + 2,6-dichlorophenolindophenol = ?
show the reaction diagram
-
D-fructose + acceptor = 2-keto-D-gulonate + reduced acceptor
show the reaction diagram
-
D-fructose + oxidized 2,6-dichlorophenolindophenol = 5-dehydro-D-fructose + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
D-fructose + O2 = ?
show the reaction diagram
-
D-fructose + NADP+ + H2O = ?
show the reaction diagram
-
chlorate + D-fructose = ?
show the reaction diagram
-
acetyl-CoA + D-fructose = CoA + 6-O-acetyl-D-fructose
show the reaction diagram
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sucrose + fructose = ?
show the reaction diagram
-
soluble starch + D-fructose = ?
show the reaction diagram
-
alpha-D-glucose 1-phosphate + D-fructose = phosphate + ?
show the reaction diagram
-
UDP-alpha-D-glucose + D-fructose = ?
show the reaction diagram
-
fructose + alpha-D-glucose 1-phosphate = ? + phosphate
show the reaction diagram
-
D-fructose + alpha-D-mannose 1-phosphate = ? + phosphate
show the reaction diagram
-
D-fructose + alpha-D-mannose 1-phosphate = ? + phosphate
show the reaction diagram
-
alpha-D-glucopyranose 1-phosphate + fructose = ? + phosphate
show the reaction diagram
-
sucrose + D-fructose = leucrose + trehalulose + 4'-alpha-D-glucosyl-leucrose + 6'-alpha-D-glucosyl-leucrose + 6'-alpha-D-glucosyl-trehalulose
show the reaction diagram
-
sucrose + fructose = turanose + ?
show the reaction diagram
-
ATP + fructose = ADP + fructose 1-phosphate
show the reaction diagram
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phosphohistidinoprotein + D-fructose = histidine-containing protein + ?
show the reaction diagram
-
glycerol 3-phosphate + D-fructose = ?
show the reaction diagram
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ADP + D-fructose = AMP + D-fructose 6-phosphate
show the reaction diagram
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ATP + D-fructose = ADP + D-fructose 5-phosphate
show the reaction diagram
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ATP + D-fructose = ADP + D-fructose 5-phosphate
show the reaction diagram
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ATP + D-fructose = ADP + O3-phosphono-D-fructose
show the reaction diagram
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ATP + D-fructose = ADP + D-fructose 6-phosphate
show the reaction diagram
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ATP + D-fructose = ADP + D-fructose 1-phosphate
show the reaction diagram
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D-fructose + acetyl phosphate = D-fructose 1-phosphate + D-fructose 6-phosphate + acetate
show the reaction diagram
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phosphoramidate + fructose = fructose 1-phosphate + NH3
show the reaction diagram
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ATP + D-fructose = ADP + D-fructose 6-phosphate
show the reaction diagram
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phosphoenolpyruvate + fructose = pyruvate + fructose 1-phosphate
show the reaction diagram
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ferulic acid + D-fructose = ?
show the reaction diagram
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phosphatidylcholine + D-fructose = phosphatidylfructose + choline
show the reaction diagram
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lactose + fructose = ?
show the reaction diagram
-
4-O-beta-D-mannopyranosyl-D-mannopyranose + D-fructose = ?
show the reaction diagram
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fructose + H2O = ?
show the reaction diagram
-
fructose + H2O = ?
show the reaction diagram
-
D-fructose + H2O = ?
show the reaction diagram
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D-fructose = D-glucose + D-mannose
show the reaction diagram
-
D-fructose = D-tagatose
show the reaction diagram
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D-fructose = D-mannose
show the reaction diagram
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D-fructose = D-glucose + D-mannose
show the reaction diagram
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D-fructose = D-mannose
show the reaction diagram
-
D-fructose = D-mannose
show the reaction diagram
-
D-Fructose + alpha-D-glucose 1-phosphate = D-Fructose 6-phosphate + D-glucose
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (454 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
D-mannitol + NAD+ = D-fructose + NADH + H+
show the reaction diagram
285751, -
-
D-sorbitol + NAD+ = D-fructose + NADH + H+
show the reaction diagram
-
-
5-dehydro-D-fructose + NADH + H+ = D-fructose + NAD+
show the reaction diagram
-
-
sorbitol + NAD+ = D-fructose + NADH + H+
show the reaction diagram
-
-
D-glucosone + NADPH + H+ = D-fructose + NADP+
show the reaction diagram
-
-
5-dehydro-D-fructose + NADPH = D-fructose + NADP+
show the reaction diagram
-
-
D-mannitol + acceptor = D-fructose + reduced acceptor
show the reaction diagram
287791, -
-
D-xylulose 5-phosphate + D-erythrose = glyceraldehyde 3-phosphate + D-fructose
show the reaction diagram
-
-
sucrose + D-glycerate = 2-O-alpha-D-glucosyl-D-glycerate + fructose
show the reaction diagram
-
-
sucrose + H2O = D-fructose + D-glucose
show the reaction diagram
-
-
D-fructose 6-phosphate + H2O = D-fructose + phosphate
show the reaction diagram
-
-
D-fructose 1-phosphate + H2O = D-fructose + phosphate
show the reaction diagram
-
D-fructose 6-phosphate + H2O = D-fructose + phosphate
show the reaction diagram
-
-
D-fructose 6-phosphate + H2O = D-fructose + phosphate
show the reaction diagram
-
-
D-fructose 6-phosphate + H2O = D-fructose + phosphate
show the reaction diagram
651559, -
-
D-fructose 6-phosphate + H2O = D-fructose + phosphate
show the reaction diagram
-
D-fructose 6-phosphate + H2O = D-fructose + phosphate
show the reaction diagram
-
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sucrose + H2O = D-glucose + D-fructose
show the reaction diagram
-
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saccharose + H2O = D-glucose + D-fructose
show the reaction diagram
-
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palatinose + H2O = alpha-D-glucopyranose + D-fructofuranose
show the reaction diagram
-
-
sucrose + H2O = D-glucose + D-fructose
show the reaction diagram
-
-
lactulose + H2O = D-galactose + D-fructose
show the reaction diagram
-
-
4-O-beta-D-galactopyranosyl-D-fructoside + H2O = beta-D-galactose + D-fructose
show the reaction diagram
-
sucrose + H2O = D-fructose + D-glucose
show the reaction diagram
-
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sucrose + H2O = D-fructose + D-glucose
show the reaction diagram
-
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sucrose + H2O = D-glucose + D-fructose
show the reaction diagram
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D-fructose-6-phosphate + H2O = D-fructose + phosphate
show the reaction diagram
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sucrose + H2O = D-fructose + D-glucose
show the reaction diagram
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2 D-glyceraldehyde = D-fructose
show the reaction diagram
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levan = di-D-fructose-2,6':2',6 dianhydride + fructose + limited levan
show the reaction diagram
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mannose = D-glucose + D-fructose
show the reaction diagram
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D-tagatose = D-fructose
show the reaction diagram
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D-psicose = D-fructose
show the reaction diagram
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D-psicose = D-fructose
show the reaction diagram
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D-psicose = D-fructose
show the reaction diagram
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D-glucose = D-fructose + D-mannose
show the reaction diagram
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D-Mannose = D-Fructose
show the reaction diagram
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D-Mannose = D-Fructose
show the reaction diagram
-
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D-Mannose = D-Fructose
show the reaction diagram
-
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D-Mannose = D-Fructose
show the reaction diagram
-
D-Mannose = D-Fructose
show the reaction diagram
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D-Mannose = D-Fructose
show the reaction diagram
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Fructose 1-phosphate + D-glucose = D-glucose 6-phosphate + fructose
show the reaction diagram
-
sucrose = palatinose + trehalulose + D-glucose + D-fructose
show the reaction diagram
-
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sucrose = D-glucose + D-fructose + [alpha-D-glucopyranosyl-(1,1)-D-fructofuranose]
show the reaction diagram
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ATP + H2O + D-fructose-[alpha-glucoside-binding protein][side 1] = ADP + phosphate + D-fructose[side 2] + [alpha-glucoside-binding protein][side 1]
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (15 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
17% activation at 2 mM
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16.1% activation at 2 mM
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minor stimulatory effect
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slight activation
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increase of activity
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favores CGTase synthesis
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acetyl-CoA carboxylase phosphorylation by the enzyme increases significantly and concentration-dependently in fructose-treated HepG2 cells in the presence of placental lactogen
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stimulates, stimulation pattern of MtrA is similar to that of MtrB
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25 mM, 1.3fold stimulation, enzyme from maize endosperm
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the activity of 5'-nucleotidase increases with increasing D-fructose concentrations (5-30 mM) in diabetic patients
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slightly stimulating
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threefold activation
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58% activation at 3 mM
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Inhibitor in Enzyme-catalyzed Reactions (102 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
PtNADP-ME1
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substrate inhibition, Ki: 1.356 mM
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incubation of Aspergillus niger glucose oxidase with 100 mM fructose for 8 days results in 88% loss in activity
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D-fructose at different concentrations, PPO activities are measured at 25°C and pH 7.0 to determine inhibitor effects of sugars on enzymatic activities. PPO activities from both cultivars show a decreasing pattern as sugar concentration in the assay medium increases
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inhibits both transfructosylation and hydrolysis activities
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25-30% inhibition at 20 mM
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competitive
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0.0015 mM almost totally inhibits uptake of D-mannose
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a 40fold excess of unlabeled D-fructose reduces maltose uptake to about 30-40% of the control rate
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0.2 M: 24% inhibition
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competitive to glucose
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inactivation of the glyoxalase system (glyoxalase I and II) in fructose fed mice
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0.95 M: 30% inhibition
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10 mM, 45% inhibition. Inhibitory effect is abolished by Ca2+
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5 mM, slight inhibition of starch hydrolysis
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reduced to 70% by the presence of 100 mM
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diminishes hdc gene expression
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10 mM, 19% inhibition
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2 mM ibuprofen and its major metabolites protect by up to 26%. Ibuprofen and the metabolites do not bind to fumarase
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formation of a Schiff base with the critical lysine residue of the enzyme is involved in inhibition of the enzyme by hexoses and pentoses
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85% residual activity at 2.5 mM
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Metals and Ions (4 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (125 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
224
-
pH 6.0, 25°C
154
-
pH 7.5, 25°C, positive cooperativity
920
-
25°C, pH 7.5, Tris-HCl
200
-
-
3.9
-
30°C, pH 6
2
-
pH 5.0, 30°C, synthetic reaction
77
-
pH 7.0, 30°C, with 30 mM alpha-D-glucose 1-phosphate as cosubstrate, wild-type enzyme
17.5
-
in 50 mM glycine-NaOH buffer (pH 9.0), at 40°C

KM Value (331 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
96
-
pH 8.6, 25°C
600
-
-
9.6
-
-
162
-
-
390
-
in 50 mM Bis-Tris propane (pH 8.0), at 50°C
400
-
-
199
-
-
1.5
-
30°C, pH 6
0.2
-
pH 5.0, 30°C, synthetic reaction
51
-
pH 7.0, 30°C, with 30 mM alpha-D-glucose 1-phosphate as cosubstrate, wild-type enzyme
1
-
pH 6.7, 85°C
50
-
pH 8.0, 37°C
51
-
in 50 mM glycine-NaOH buffer (pH 9.0), at 40°C

Ki Value (30 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1356
-
-
27
-
-
0.23
-
inhibition with respect to glucose
61.5
-
55°C, pH 4.6, invertase 2

IC50 Value (4 results)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
40
-
pH 7.5, 30°C, phosphopfructokinase reaction
40
-
pH 7.5, 30°Cphosphopfructokinase reaction

References & Links

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Links to other databases for D-fructofuranose

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EXTERNAL LINKS
ChEBI
PubChem
UniChem