BRENDA - Enzyme Database
show all sequences of 3.4.22.B14

Structure-based design, synthesis, and biological evaluation of a series of novel and reversible inhibitors for the severe acute respiratory syndrome-coronavirus papain-like protease

Ghosh, A.K.; Takayama, J.; Aubin, Y.; Ratia, K.; Chaudhuri, R.; Baez, Y.; Sleeman, K.; Coughlin, M.; Nichols, D.B.; Mulhearn, D.C.; Prabhakar, B.S.; Baker, S.C.; Johnson, M.E.; Mesecar, A.D.; J. Med. Chem. 52, 5228-5240 (2009) View publication on PubMedView publication on EuropePMC

Data extracted from this reference:

Cloned(Commentary)
Cloned (Commentary)
Organism
expressed in Escherichia coli
Severe acute respiratory syndrome-related coronavirus
Inhibitors
Inhibitors
Commentary
Organism
Structure
2,6-dimethyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
2,N-dimethyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
2-methoxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
2-methoxymethyl-5-nitrobenzoic acid methyl ester
-
Severe acute respiratory syndrome-related coronavirus
2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
2-methyl-N-[1-(naphthalen-2-yl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
3-methoxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
3-methyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
4-amino-N-[(R)-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
4-amino-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
4-methoxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
4-methyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
5-amino-2-methoxymethyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
5-amino-2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
5-amino-2-methyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
5-cyano-2-methyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
5-iodo-2-methyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
5-methylamino-2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
5-N-acetylamino-2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
5-N-tert-butoxycarbonylmethylamino-2-methyl-N'-[(R)-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
additional information
not inhibited by 2-hydroxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide, 4-N'-tert-butoxycarbonylamino-N-[(R)-1-(2-naphthyl)ethyl]-benzamide, 2-methyl-N-[1-(2-naphthyl)propyl]benzamide, and 2-methyl-N-[1-(2-naphthyl)benzyl]benzamide
Severe acute respiratory syndrome-related coronavirus
N-methyl-5-methylamino-2-methyl-N'-[(R)-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
Organism
Organism
UniProt
Commentary
Textmining
Severe acute respiratory syndrome-related coronavirus
-
-
-
Purification (Commentary)
Purification (Commentary)
Organism
-
Severe acute respiratory syndrome-related coronavirus
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
L-Arg-L-Leu-L-Arg-Gly-Gly-7-amido-4-methylcoumarin + H2O
-
709449
Severe acute respiratory syndrome-related coronavirus
L-Arg-L-Leu-L-Arg-Gly-Gly + 7-amino-4-methylcoumarin
-
-
-
?
Synonyms
Synonyms
Commentary
Organism
PLpro
-
Severe acute respiratory syndrome-related coronavirus
IC50 Value
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
0.00046
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
5-methylamino-2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
0.00056
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
5-amino-2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
0.00056
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
5-amino-2-methyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
0.0013
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
N-methyl-5-methylamino-2-methyl-N'-[(R)-1-(1-naphthyl)ethyl]benzamide
0.0014
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
2-methoxymethyl-5-nitrobenzoic acid methyl ester
0.0023
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
0.00264
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
5-N-acetylamino-2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
0.0027
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
5-iodo-2-methyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
0.0048
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
5-N-tert-butoxycarbonylmethylamino-2-methyl-N'-[(R)-1-(1-naphthyl)ethyl]benzamide
0.0052
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
5-amino-2-methoxymethyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
0.0087
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
2-methyl-N-[1-(naphthalen-2-yl)ethyl]benzamide
0.0111
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
5-cyano-2-methyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
0.0121
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
2,6-dimethyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.0135
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
3-methoxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.0148
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
3-methyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.0226
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
2,N-dimethyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.0248
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
4-amino-N-[(R)-1-(1-naphthyl)ethyl]benzamide
0.0291
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
4-methyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.0461
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
4-amino-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.09
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
2-methoxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.149
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
4-methoxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide
Cloned(Commentary) (protein specific)
Commentary
Organism
expressed in Escherichia coli
Severe acute respiratory syndrome-related coronavirus
IC50 Value (protein specific)
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
0.00046
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
5-methylamino-2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
0.00056
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
5-amino-2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
0.00056
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
5-amino-2-methyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
0.0013
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
N-methyl-5-methylamino-2-methyl-N'-[(R)-1-(1-naphthyl)ethyl]benzamide
0.0014
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
2-methoxymethyl-5-nitrobenzoic acid methyl ester
0.0023
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
0.00264
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
5-N-acetylamino-2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
0.0027
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
5-iodo-2-methyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
0.0048
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
5-N-tert-butoxycarbonylmethylamino-2-methyl-N'-[(R)-1-(1-naphthyl)ethyl]benzamide
0.0052
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
5-amino-2-methoxymethyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
0.0087
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
2-methyl-N-[1-(naphthalen-2-yl)ethyl]benzamide
0.0111
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
5-cyano-2-methyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
0.0121
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
2,6-dimethyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.0135
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
3-methoxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.0148
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
3-methyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.0226
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
2,N-dimethyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.0248
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
4-amino-N-[(R)-1-(1-naphthyl)ethyl]benzamide
0.0291
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
4-methyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.0461
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
4-amino-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.09
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
2-methoxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide
0.149
-
in 50 mM HEPES, pH 7.5
Severe acute respiratory syndrome-related coronavirus
4-methoxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
2,6-dimethyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
2,N-dimethyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
2-methoxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
2-methoxymethyl-5-nitrobenzoic acid methyl ester
-
Severe acute respiratory syndrome-related coronavirus
2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
2-methyl-N-[1-(naphthalen-2-yl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
3-methoxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
3-methyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
4-amino-N-[(R)-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
4-amino-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
4-methoxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
4-methyl-N-[(R)-1-(2-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
5-amino-2-methoxymethyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
5-amino-2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
5-amino-2-methyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
5-cyano-2-methyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
5-iodo-2-methyl-N-[1-methyl-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
5-methylamino-2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
5-N-acetylamino-2-methyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
5-N-tert-butoxycarbonylmethylamino-2-methyl-N'-[(R)-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
additional information
not inhibited by 2-hydroxy-N-[(R)-1-(2-naphthyl)ethyl]benzamide, 4-N'-tert-butoxycarbonylamino-N-[(R)-1-(2-naphthyl)ethyl]-benzamide, 2-methyl-N-[1-(2-naphthyl)propyl]benzamide, and 2-methyl-N-[1-(2-naphthyl)benzyl]benzamide
Severe acute respiratory syndrome-related coronavirus
N-methyl-5-methylamino-2-methyl-N'-[(R)-1-(1-naphthyl)ethyl]benzamide
-
Severe acute respiratory syndrome-related coronavirus
Purification (Commentary) (protein specific)
Commentary
Organism
-
Severe acute respiratory syndrome-related coronavirus
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
L-Arg-L-Leu-L-Arg-Gly-Gly-7-amido-4-methylcoumarin + H2O
-
709449
Severe acute respiratory syndrome-related coronavirus
L-Arg-L-Leu-L-Arg-Gly-Gly + 7-amino-4-methylcoumarin
-
-
-
?
Other publictions for EC 3.4.22.B14
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Synonyms
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
755215
Niemeyer
The papain-like protease dete ...
SARS coronavirus FRA
PLoS Pathog.
14
e1007296
2018
-
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1
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1
1
-
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-
752911
Hu
Transmissible gastroenteritis ...
Transmissible gastroenteritis virus
BioMed Res. Int.
2017
7089091
2017
-
-
-
-
3
-
-
-
-
-
-
-
-
1
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2
-
1
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3
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2
-
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1
1
-
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-
754425
Daczkowski
Structural insights into the ...
Severe acute respiratory syndrome-related coronavirus
J. Mol. Biol.
429
1661-1683
2017
-
-
-
1
-
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1
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1
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1
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1
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1
1
-
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-
755428
Li
SARS coronavirus papain-like ...
Severe acute respiratory syndrome-related coronavirus
Sci. Rep.
6
25754
2016
-
-
-
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1
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1
1
-
-
-
752708
Bekes
SARS hCoV papain-like proteas ...
Severe acute respiratory syndrome-related coronavirus, Middle East respiratory syndrome-related coronavirus
Biochem. J.
468
215-226
2015
-
-
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2
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8
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8
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2
2
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754125
Kong
Structural view and substrate ...
infectious bronchitis virus, infectious bronchitis virus Beaudette
J. Biol. Chem.
290
7160-7168
2015
-
-
1
1
-
-
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-
-
2
-
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11
-
1
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1
-
1
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11
-
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-
2
2
709746
Wojdyla
Papain-like protease 1 from tr ...
Transmissible gastroenteritis virus, Transmissible gastroenteritis virus Purdue
J. Virol.
84
10063-10073
2010
-
-
1
1
-
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-
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3
-
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1
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8
-
2
-
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1
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1
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1
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8
-
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-
709752
Gadlage
Exchange of the coronavirus re ...
Murine hepatitis virus
J. Virol.
84
6894-6898
2010
-
-
-
-
-
-
-
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1
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3
-
1
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3
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-
-
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709449
Ghosh
Structure-based design, synthe ...
Severe acute respiratory syndrome-related coronavirus
J. Med. Chem.
52
5228-5240
2009
-
-
1
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-
22
-
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1
-
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1
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-
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1
-
1
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21
-
-
1
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21
22
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