Information on EC 3.5.1.2 - glutaminase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
3.5.1.2
-
RECOMMENDED NAME
GeneOntology No.
glutaminase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
L-glutamine + H2O = L-glutamate + NH3
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
carboxylic acid amide hydrolysis
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Alanine, aspartate and glutamate metabolism
-
-
Arginine biosynthesis
-
-
D-Glutamine and D-glutamate metabolism
-
-
glutamate and glutamine metabolism
-
-
L-citrulline biosynthesis
-
-
L-glutamine degradation I
-
-
Metabolic pathways
-
-
SYSTEMATIC NAME
IUBMB Comments
L-glutamine amidohydrolase
-
CAS REGISTRY NUMBER
COMMENTARY hide
9001-47-2
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
strain PCC 7120
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
Bacillus cereus MTCC 1305
-
UniProt
Manually annotated by BRENDA team
ATCC 14580
UniProt
Manually annotated by BRENDA team
ATCC 14580
UniProt
Manually annotated by BRENDA team
MTCC 10401, isolated from Gangotri region of Uttarakhand Himalaya
-
-
Manually annotated by BRENDA team
Bacillus sp. LKG-01
MTCC 10401, isolated from Gangotri region of Uttarakhand Himalaya
-
-
Manually annotated by BRENDA team
strain 168, ATCC 23857D-5
SwissProt
Manually annotated by BRENDA team
gene prgA
-
-
Manually annotated by BRENDA team
Clostridium welchii
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
gene CagahA
-
-
Manually annotated by BRENDA team
gene CagahA
-
-
Manually annotated by BRENDA team
gene CngahA
-
-
Manually annotated by BRENDA team
gene CngahA
-
-
Manually annotated by BRENDA team
strain W3110
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
male White Leghorn chicken
-
-
Manually annotated by BRENDA team
Hypocria jecorina
-
-
-
Manually annotated by BRENDA team
KCTC3594
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
no activity in Gallus gallus
no liver-type isozyme, LGA, activity in the brain
-
-
Manually annotated by BRENDA team
NRC 510
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
ATCC 21025
-
-
Manually annotated by BRENDA team
Rattus norvegicus Sprague-Dawley
Sprague-Dawley
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
lizard
-
-
Manually annotated by BRENDA team
ATCC 11859
-
-
Manually annotated by BRENDA team
strain NYW-81
-
-
Manually annotated by BRENDA team
strain NYW-81
-
-
Manually annotated by BRENDA team
strain LG-10, isolated from the estuarine fish Chanos chanos, from gills, skin, and gut contents
-
-
Manually annotated by BRENDA team
strain LG-10, isolated from the estuarine fish Chanos chanos, from gills, skin, and gut contents
-
-
Manually annotated by BRENDA team
gene slr2079
UniProt
Manually annotated by BRENDA team
gene trpG
-
-
Manually annotated by BRENDA team
Triticale sp.
-
-
-
Manually annotated by BRENDA team
MSS2
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
-
treating cells that coexpressed Mek2-K101A and kidney-type glutaminase with suboptimal level of BPTES leads to synergistic inhibition on cell proliferation
metabolism
-
glutaminase C is the first enzyme in glutaminolysis
physiological function
additional information
-
Ile221-Leu533 is the catalytic domain of kidney-type glutaminase
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-oxo-glutaramate + H2O
?
show the reaction diagram
-
-
-
-
?
2-oxo-succinamate + H2O
?
show the reaction diagram
-
-
-
-
?
5-methoxy-2,5-dioxopentanoic acid + H2O
methanol + 2-oxoglutaric acid
show the reaction diagram
-
-
-
-
?
6-diazo-5-oxo-L-norleucine + H2O
?
show the reaction diagram
-
the nucleophilic attack of Ser286 sidechain on 6-diazo-5-oxo-L-norleucine releases the diazo group (N2) from the inhibitor and results in the formation of an enzyme-inhibitor complex
-
-
?
alpha-methyl-DL-Gln + H2O
?
show the reaction diagram
-
-
-
-
?
beta-cyanoalanine + H2O
?
show the reaction diagram
-
0.2% of the activity with L-Gln
-
-
?
Cbz-Gln-Gly + H2O
Cbz-Glu-Gly + NH3
show the reaction diagram
-
-
-
-
?
Cbz-L-Gln + H2O
Cbz-L-Glu + NH3
show the reaction diagram
-
-
-
-
?
D-Asn + H2O
D-Asp + NH3
show the reaction diagram
D-Asn + H2O
D-aspartate + NH3
show the reaction diagram
-
less 0.1% of the activity with L-glutamine and H2O as co-substrate
-
-
?
D-Asn + hydroxylamine
D-2-amino-4-(hydroxylamino)-4-oxobutanoic acid + NH3
show the reaction diagram
-
-
-
-
?
D-asparagine + H2O
?
show the reaction diagram
D-asparagine + H2O
D-aspartate
show the reaction diagram
44% activity
-
-
?
D-asparagine + H2O
D-aspartate + NH3
show the reaction diagram
D-gamma-glutamyl-ethylester + H2O
D-Glu + ethanol
show the reaction diagram
-
-
-
-
?
D-gamma-glutamyl-ethylester + hydroxylamine
D-gamma-glutamyl hydroxamate + ethanol
show the reaction diagram
-
-
-
-
?
D-gamma-glutamyl-hydrazide + H2O
D-Glu + hydroxyhydrazine
show the reaction diagram
-
-
-
-
?
D-gamma-glutamyl-hydrazide + hydroxylamine
D-gamma-glutamyl hydroxamate + hydroxyhydrazine
show the reaction diagram
-
-
-
-
?
D-gamma-glutamyl-methylester + H2O
D-Glu + methanol
show the reaction diagram
-
-
-
-
?
D-gamma-glutamyl-methylester + hydroxylamine
L-gamma-glutamyl hydroxamate + methanol
show the reaction diagram
-
-
-
-
?
D-Gln + H2O
D-Glu + NH3
show the reaction diagram
D-Gln + hydroxylamine
D-gamma-glutamyl hydroxamate + NH3
show the reaction diagram
-
glutaminase A and B
-
?
D-glutamine + H2O
D-glutamate + NH3
show the reaction diagram
D-theanine + H2O
D-glutamate + ethylamine
show the reaction diagram
-
-
-
-
?
D-theanine + H2O
N-ethyl-D-glutamic acid
show the reaction diagram
57% activity
-
-
?
gamma-ethyl glutamate + H2O
Glu + ethanol
show the reaction diagram
-
-
-
-
?
gamma-ethyl glutamate + hydroxylamine
gamma-glutamyl hydroxamate + ethanol
show the reaction diagram
-
-
-
-
?
gamma-glutamyl hydroxamate + NH2OH
?
show the reaction diagram
-
36.3% of the activity with L-glutamine and H2O as co-substrate
-
-
?
gamma-glutamyl-hydrazide + H2O
Glu + hydroxyhydrazine
show the reaction diagram
-
-
-
-
?
gamma-glutamyl-hydrazide + hydroxylamine
Glu + hydroxyhydrazine
show the reaction diagram
-
-
-
-
?
gamma-glutamyl-hydroxamate + H2O
Glu + hydroxylamine
show the reaction diagram
-
-
-
-
?
gamma-glutamyl-hydroxamate + hydroxylamine
gamma-glutamyl hydroxamate + hydroxylamine
show the reaction diagram
-
-
-
-
-
gamma-glutamyl-methoxyamide + H2O
Glu + N-hydroxy-O-methylhydroxylamine
show the reaction diagram
-
-
-
-
?
gamma-glutamyl-methoxyamide + hydroxylamine
gamma-glutamyl hydroxamate + N-hydroxy-O-methylhydroxylamine
show the reaction diagram
-
-
-
-
?
gamma-glutamyl-methylamide + H2O
Glu + N-methylhydroxylamine
show the reaction diagram
gamma-glutamyl-methylamide + hydroxylamine
gamma-glutamyl hydroxamate + N-methylhydroxylamine
show the reaction diagram
-
-
-
-
?
gamma-L-glutamyl-4-nitroanilide + H2O
L-glutamate 4-nitroanilide + NH3
show the reaction diagram
-
102% activity compared to L-glutamine
-
-
?
gamma-methyl glutamate + H2O
Glu + methanol
show the reaction diagram
-
-
-
r
gamma-methyl glutamate + hydroxylamine
gamma-glutamyl hydroxamate + methanol
show the reaction diagram
-
-
-
-
?
gamma-thioethyl glutamate + H2O
Glu + thioethanol
show the reaction diagram
-
-
-
-
?
gamma-thioethyl glutamate + hydroxylamine
gamma-glutamyl hydroxamate + ?
show the reaction diagram
-
-
-
-
?
gamma-thiomethyl glutamate + H2O
Glu + thiomethanol
show the reaction diagram
-
-
-
-
?
gamma-thiomethyl glutamate + hydroxylamine
gamma-glutamyl hydroxamate + ?
show the reaction diagram
-
-
-
-
?
Gln + H2O
Glu + NH3
show the reaction diagram
Glu + hydroxylamine
gamma-glutamyl hydroxamate + H2O
show the reaction diagram
-
-
-
-
?
glutaramate + H2O
?
show the reaction diagram
-
-
-
-
?
Gly-Asn + H2O
Gly-Asp + NH3
show the reaction diagram
-
-
-
-
?
Gly-Gln + H2O
Gly-Glu + NH3
show the reaction diagram
-
-
-
-
?
L-Ala-Gln + H2O
L-Ala-L-Glu + NH3
show the reaction diagram
-
-
-
-
?
L-Asn + H2O
L-Asp + NH3
show the reaction diagram
L-Asn + H2O
L-aspartate + NH3
show the reaction diagram
-
20.6% of the activity with L-glutamine and H2O as co-substrate
-
-
?
L-Asn + hydroxylamine
L-2-amino-4-(hydroxylamino)-4-oxobutanoic acid + NH3
show the reaction diagram
-
-
-
-
?
L-asparagine + H2O
?
show the reaction diagram
L-asparagine + H2O
L-aspartate
show the reaction diagram
51% activity
-
-
?
L-asparagine + H2O
L-aspartate + NH3
show the reaction diagram
L-gamma-glutamyl-4-nitroanilide + H2O
L-glutamate 4-nitroanilide + NH3
show the reaction diagram
L-gamma-glutamyl-anilide + H2O
L-Glu + aniline
show the reaction diagram
-
-
-
-
?
L-gamma-glutamyl-anilide + hydroxylamine
L-gamma-glutamyl hydroxamate + aniline
show the reaction diagram
-
-
-
-
?
L-gamma-glutamyl-ethylester + H2O
L-Glu + ethanol
show the reaction diagram
-
-
-
-
?
L-gamma-glutamyl-hydrazide + H2O
L-Glu + hydroxyhydrazine
show the reaction diagram
L-gamma-glutamyl-hydrazide + hydroxylamine
L-gamma-glutamyl hydroxamate + hydroxyhydrazine
show the reaction diagram
-
-
-
-
?
L-gamma-glutamyl-L-Ala + H2O
?
show the reaction diagram
-
-
-
-
?
L-gamma-glutamyl-L-Ala + hydroxylamine
gamma-glutamyl hydroxamate + Ala
show the reaction diagram
-
-
-
-
?
L-gamma-glutamyl-L-epsilon-Lys + H2O
?
show the reaction diagram
-
-
-
-
?
L-gamma-glutamyl-L-epsilon-Lys + hydroxylamine
?
show the reaction diagram
-
-
-
-
?
L-gamma-glutamyl-L-Glu + H2O
?
show the reaction diagram
-
-
-
-
?
L-gamma-glutamyl-L-Glu + hydroxylamine
?
show the reaction diagram
-
-
-
-
?
L-gamma-glutamyl-methylester + H2O
L-Glu + methanol
show the reaction diagram
L-gamma-glutamyl-methylester + hydroxylamine
L-gamma-glutamyl hydroxamate + methanol
show the reaction diagram
-
-
-
-
?
L-gamma-glutamyl-p-nitroanilide + H2O
?
show the reaction diagram
-
-
-
?
L-gamma-glutamylhydrazine + H2O
?
show the reaction diagram
-
-
-
?
L-Gln + H2O
L-Glu + NH3
show the reaction diagram
L-Gln + hydroxylamine
L-gamma-glutamyl hydroxamate + NH3
show the reaction diagram
L-glutamate-p-nitroanilide + H2O
L-glutamate + 4-nitroaniline
show the reaction diagram
L-glutamic acid + H2O
?
show the reaction diagram
L-glutamic acid + NH2OH
gamma-glutamyl hydroxamate
show the reaction diagram
-
0.9% of the activity with L-glutamine and H2O as co-substrate
-
-
?
L-glutamine + ethylamine
theanine + NH3
show the reaction diagram
L-glutamine + H2O
L-glutamate + NH3
show the reaction diagram
L-glutamine + H2O
L-glutamic acid + NH3
show the reaction diagram
L-glutamine + NH2OH
?
show the reaction diagram
-
10.3% of the activity with L-glutamine and H2O as co-substrate
-
-
?
L-glutaminyl-L-asparagine + H2O
?
show the reaction diagram
L-isoglutamine + H2O
?
show the reaction diagram
-
-
-
-
?
L-Leu-Ala-Asn + H2O
L-Leu-Ala-Asp + NH3
show the reaction diagram
-
-
-
-
?
L-Leu-Gln-Gly + H2O
L-Leu-Glu-Gly + NH3
show the reaction diagram
-
-
-
-
?
L-Leu-Gly-Asn + H2O
L-Leu-Gly-Asp + NH3
show the reaction diagram
-
-
-
-
?
L-Pro-Leu-Gly-Asn + H2O
L-Pro-Leu-Gly-Asp + NH3
show the reaction diagram
-
-
-
-
?
L-Pro-Leu-Gly-Gln + H2O
L-Pro-Leu-Gly-Glu + NH3
show the reaction diagram
-
-
-
-
?
L-theanine + H2O
L-glutamate + ethylamine
show the reaction diagram
-
-
-
-
?
L-theanine + H2O
N-ethyl-L-glutamic acid
show the reaction diagram
71% activity
-
-
?
nitrocefin + H2O
(2R)-2-{(R)-carboxy[2-(thiophen-2-yl)acetamido]methyl}-5-[(E)-2-(2,4-dinitrophenyl)ethenyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
show the reaction diagram
succinamate + H2O
?
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
L-Gln + H2O
L-Glu + NH3
show the reaction diagram
L-glutamine + H2O
L-glutamate + NH3
show the reaction diagram
L-glutamine + H2O
L-glutamic acid + NH3
show the reaction diagram
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
arsenate
-
50 mM, 800% of the relative activity without addition
Ca2+
-
0.5-1.0 mM, 2fold activation of NEM-insensitive enzyme
chloride
-
competes with phosphate for binding to the catalytic Ser291, at high concentration (500 mM NaCl) it can dislodge phosphate from its site and shift the protein equilibrium to lower-order oligomers
Cl-
Triticale sp.
-
1 mM, markedly activates the enzyme
NaBr
-
0.25 M, 1.2-1.3fold activation
NaF
-
0.25 M, 1.2-1.3fold activation
NaI
-
0.25 M, 1.2-1.3fold activation
NH4+
-
Ka 1 mM
phosphate
sulfate
-
50 mM, 700% of the relative activity without addition
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2R)-1-(2-formyl-3,6-dihydroxy-5-methoxycyclohexa-1,4-dien-1-yl)tridecan-2-yl acetate
-
-
(2R)-1-(2-hydroxy-5-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)pentadecan-2-yl acetate
-
-
(2R)-1-(2-hydroxy-5-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tridecan-2-yl acetate
-
-
(2R)-1-(3,6-dihydroxy-5-methoxycyclohexa-1,4-dien-1-yl)tridecan-2-yl acetate
-
-
(2R)-1-(5-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)pentadecan-2-yl acetate
-
-
(2R)-1-(5-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tridecan-2-yl acetate
-
-
(2R)-1-[3-(acetyloxy)-6-hydroxy-5-methoxycyclohexa-1,4-dien-1-yl]pentadecan-2-yl acetate
-
-
(2R)-1-[3-(acetyloxy)-6-hydroxy-5-methoxycyclohexa-1,4-dien-1-yl]tridecan-2-yl acetate
-
-
(2S)-1-(5-methoxycyclohexa-1,4-dien-1-yl)heptan-2-ol
-
-
(2S)-2-amino-6-imino-5-oxohexanoic acid
-
-
1,2-naphthoquinone 4-sulfonate
-
-
1,4-Naphthoquinone
-
-
1-amino-8-naphthol-2,4-disulfonic acid
-
weak
2,2-dimethyl-5-[4-(methylsulfanyl)phenyl]-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one
-
97% inhibition at 0.05 mM
2,2-dimethyl-5-[4-(naphthalen-1-yl)phenyl]-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one
-
97% inhibition at 0.05 mM
2,2-dimethyl-5-[4-(propan-2-yl)phenyl]-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one
-
91% inhibition at 0.05 mM
2,4-dinitro-1-naphthol-7-sulfonic acid
-
i.e. flavianic acid
2-bromo-4-(2,2-dimethyl-4-oxo-1,2,3,4,5,6-hexahydrobenzo[a]phenanthridin-5-yl)-6-methoxyphenyl acetate
-
84% inhibition at 0.05 mM
2-hydroxy-5-methoxy-3-tridecylcyclohexa-2,5-diene-1,4-dione
-
-
2-methoxy-6-pentadecylcyclohexa-2,5-diene-1,4-dione
-
-
2-methoxy-6-tridecylcyclohexa-2,5-diene-1,4-dione
-
-
2-methyl-5-[(7Z)-pentadec-7-en-1-yl]cyclohexa-1,4-diene-1,3-diol
-
-
2-methyl-5-[(7Z)-tridec-7-en-1-yl]cyclohexa-1,4-diene-1,3-diol
-
-
2-oxoglutarate
2-phenyl isoindolin-1-one
-
-
-
2-phenylbenzo[d] isoxazol-3(2H)-one
-
-
-
2-phenylbenzo[d]isothiazol-3(2H)-one
-
-
3-[(2S)-2-hydroxypentadecyl]-5-methoxycyclohexa-2,5-dien-1-ol
-
-
4-hydroxy-2-methoxy-6-(2-oxopentadecyl)cyclohexa-2,5-dien-1-yl acetate
-
-
5,5'-(sulfanediyldiethane-2,1-diyl)bis(1,3,4-thiadiazol-2-amine)
-
-
5-(3-bromo-4,5-dimethoxyphenyl)-2,2-dimethyl-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one
-
complete inhibition at 0.05 mM
5-(3-bromo-4-(dimethylamino)phenyl)-2,2-dimethyl-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one
-
-
5-(3-chloro-4,5-dimethoxyphenyl)-2,2-dimethyl-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one
-
88% inhibition at 0.05 mM
5-(4-tert-butylphenyl)-2,2-dimethyl-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one
-
99% inhibition at 0.05 mM
5-[(6Z)-13-(3,5-dihydroxy-4-methylcyclohexa-1,4-dien-1-yl)tridec-6-en-1-yl]-2-methylbenzene-1,3-diol
-
-
5-[(6Z)-13-(3,5-dihydroxy-4-methylcyclohexa-1,4-dien-1-yl)tridec-6-en-1-yl]benzene-1,3-diol
-
-
5-[(6Z)-13-(3-hydroxy-5-methoxycyclohexa-1,4-dien-1-yl)tridec-6-en-1-yl]benzene-1,3-diol
-
-
5-[(7Z)-13-(3-hydroxy-5-methoxyphenyl)tridec-7-en-1-yl]-2-methylcyclohexa-1,4-diene-1,3-diol
-
-
5-[(7Z)-15-(3-hydroxy-5-methoxyphenyl)pentadec-7-en-1-yl]-2-methylcyclohexa-1,4-diene-1,3-diol
-
-
5-[(7Z)-pentadec-7-en-1-yl]cyclohexa-1,4-diene-1,3-diol
-
-
5-[(7Z)-tridec-7-en-1-yl]cyclohexa-1,4-diene-1,3-diol
-
-
5-[(8Z)-15-(3,5-dihydroxy-4-methylcyclohexa-1,4-dien-1-yl)pentadec-8-en-1-yl]-2-methylbenzene-1,3-diol
-
-
5-[(8Z)-15-(3,5-dihydroxy-4-methylcyclohexa-1,4-dien-1-yl)pentadec-8-en-1-yl]benzene-1,3-diol
-
-
5-[(8Z)-15-(3-hydroxy-5-methoxycyclohexa-1,4-dien-1-yl)pentadec-8-en-1-yl]benzene-1,3-diol
-
-
5-[14-(3-hydroxy-5-methoxycyclohexa-1,4-dien-1-yl)tetradecyl]benzene-1,3-diol
-
-
5-[3-bromo-4-(dimethylamino)phenyl]-2,2-dimethyl-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one
5-[4-(diethylamino)phenyl]-2,2-dimethyl-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one
-
96% inhibition at 0.05 mM
5-[4-(dimethylamino)phenyl]-2,2-dimethyl-2,3,5,6-tetrahydrobenzo[a]phenanthridin-4(1H)-one
-
59% inhibition at 0.05 mM
5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]-N-[2-(4-phenylpiperidin-1-yl)ethyl]pentanamide
-
-
5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]-N-[2-(piperidin-1-yl)ethyl]pentanamide
-
-
5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]-N-[2-(pyrrolidin-1-yl)ethyl]pentanamide
-
-
5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]-N-[4-(trifluoromethyl)benzyl]pentanamide
-
-
6-diazo-5-oxo-L-norleucine
6-diazo-5-oxo-Lnorleucine
-
time-dependent inhibition
-
8-[3-bromo-4-(diethylamino)phenyl]-11,11-dimethyl-8,10,11,12-tetrahydrobenzo[a][4,7]phenanthrolin-9(7H)-one
-
96% inhibition at 0.05 mM
8-[3-bromo-4-(dimethylamino)phenyl]-11,11-dimethyl-8,10,11,12-tetrahydrobenzo[a][4,7]phenanthrolin-9(7H)-one
-
91% inhibition at 0.05 mM
Al3+
-
46% residual activity at 1 mM
anthraquinone-1,8-disulfonate
-
-
apomorphine
-
competitive inhibition, i.e. 5,6,6a,7-tetrahydro-6-methyl-4H-dibenzo[de,g]quinoline-10,11-diol
arsenate
-
0.5 M, 74% inhibition
azaserine
-
about 19% inhibition at about 1 mM
BaCl2
-
inhibition to a variable extent
Berberine
-
-
bicarbonate
-
0.5 M, complete inhibition
bis-2-(5-phenylacetamido-1,2,4-thiadiazol-2-yl) ethyl sulfide
-
i.e. BPTES, binds to an allosteric pocket at the dimer interface of kidney-type glutaminase, triggering a dramatic conformational change of the key loop (Glu312-Pro329) near the catalytic site and rendering it inactive, allosteric inhibition. Binding of BPTES stabilizes the inactive tetramers of the catalytic domain of kidney-type glutaminase. The binding mode of BPTES on the hydrophobic pocket determines its specificity to the kidney-type glutaminase isoform KGA
bis-2-(5-phenylacetamido-1,2,4-thiadiazol-2-yl)ethyl sulfide
bis-2-(5-phenylacetimido-1,2,4,thiadiazol-2-yl)ethyl sulfide
; inhibits specifically GLS1 and its splice variant GAC, two inhibitor molecules bind at an interface region of the GAC tetramer in a manner that appears to lock the GAC tetramer into a nonproductive conformation, binding structure and mechanism of glutaminase inhibition, overview; inhibits specifically GLS1 splice variant GAC, two inhibitor molecules bind at an interface region of the GAC tetramer in a manner that appears to lock the GAC tetramer into a nonproductive conformation, binding structure and mechanism of glutaminase inhibition, overview
bis-2-(5-phenylacetimido-1,2,4-thiadiazol-2-yl) ethyl sulfide
-
glutaminase-1-selective inhibitor
-
bis-2-(5-phenylacetimido-1,2,4-thiadiazol-2-yl)ethyl sulfide
-
uncompetitive inhibition
Bromocresol green
-
-
bromocresol purple
-
-
CaCl2
-
inhibition to a variable extent
Cd2+
complete inhibition at 50 mM
chelerythrine
-
competitive inhibition, i.e. 1,2-dimethoxy-N-methyl[1,3]benzodioxolo[5,6-c]phenanthridinium
citrate
-
enzyme from mesenteric lymph nodes
Cl-
-
0.5 M, complete inhibition
CN-
-
0.5 M, complete inhibition
CoCl2
-
14% inhibition at 1 mM
CuCl2
-
20% inhibition at 1 mM, 17% at 0.1 mM
CuSO4
-
inhibition to a variable extent
D-glucose
-
negative influence in media with glucose as carbon source
diazo-5-oxo-L-norleucine
diethyl dicarbonate
-
-
dimethyl 2-[1-(4-tert-butylbenzoyl)-2,2,7-trimethyl-3-methylidene-2,3-dihydroquinolin-4(1H)-ylidene]-1,3-dithiole-4,5-dicarboxylate
-
97% inhibition at 0.05 mM
diphenylarsinic acid
-
the protein level of GAC significantly decrease in an concentration manner. The PAG activities are also decreased in parallel with the decrease in GAC
diphosphate
-
0.1 M, 98% inhibition
dithiothreitol
-
complete inhibition at 1 mM
ebselen
-
mixed non-competitive inhibition, i.e. 2-phenyl-1,2-benzisoselenazol-3[2H]-one
Fe2+
-
92% residual activity at 1 mM
FeCl3
-
glutaminase II
glufosinate ammonium
-
about 23% inhibition at about 1 mM
-
glutamate
iodoacetamide
iodoacetate
-
50 mM, strongly inhibited, 80% inhibition, especially more strongly with a progress of purification steps
L-glutamate
L-Glutamic acid
Triticale sp.
-
5 mM, about a 40% inhibition
L-glutamine
L-methionine sulfoximine
-
about 21% inhibition at about 1 mM
Mersalyl
metformin
-
68% inhibition at 100 mM
methylene blue
-
0.005%, irreversible inactivation
MgCl2
-
20% inhibition at 1 mM, 12% at 0.1 mM
MnCl2
-
22% inhibition at 1 mM, 13% at 0.1 mM
N'-[(E)-[3-bromo-4-(dimethylamino)phenyl]methylidene]-2-(9-oxoacridin-10(9H)-yl)acetohydrazide
-
93% inhibition at 0.05 mM
N,N'-[sulfanediylbis(ethane-2,1-diyl-1,3,4-thiadiazole-5,2-diyl)]bis(2-phenylacetamide)
-
-
N-(2-aminoethyl)-5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]pentanamide
-
-
N-(5-[2-[2-(5-amino-[1,3,4]thiadiazol-2-yl)-ethylsulfanyl]-ethyl]-[1,3,4]thiadiazol-2-yl)-2-phenyl-acetamide
-
-
N-benzyl-5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]pentanamide
-
-
N-methyl-5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]-N-[2-(pyrrolidin-1-yl)ethyl]pentanamide
-
-
N-tert-butyl-5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]pentanamide
-
-
N-tert-butyl-N-methyl-5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]pentanamide
-
-
N-[2-(1-methylpyrrolidin-2-yl)ethyl]-5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]pentanamide
-
-
N-[2-(4-hydroxypiperidin-1-yl)ethyl]-5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]pentanamide
-
-
N-[2-(diethylamino)ethyl]-5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]pentanamide
-
-
-
N-[4-(dimethylamino)benzyl]-5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]pentanamide
-
-
N-[4-[4-(5-amino-1,3,4-thiadiazol-2-yl)butyl]-1,3-thiazol-2-yl]-2-phenylacetamide
-
-
N-[5-(2-[[2-(5-amino-1,3,4-thiadiazol-2-yl)ethyl]sulfinyl]ethyl)-1,3,4-thiadiazol-2-yl]-2-phenylacetamide
-
-
N-[5-[2-(5-amino-1,3,4-thiadiazol-2-yl)ethyl]-1,3,4-thiadiazol-2-yl]-2-phenylacetamide
-
-
N-[5-[4-(5-amino-1,3,4-thiadiazol-2-yl)butyl]-1,3,4-thiadiazol-2-yl]-2-(4-fluorophenyl)acetamide
-
-
N-[5-[4-(5-amino-1,3,4-thiadiazol-2-yl)butyl]-1,3,4-thiadiazol-2-yl]-2-(4-methylphenyl)acetamide
-
-
N-[5-[4-(5-amino-1,3,4-thiadiazol-2-yl)butyl]-1,3,4-thiadiazol-2-yl]-2-cyclohexylacetamide
-
-
N-[5-[4-(5-amino-1,3,4-thiadiazol-2-yl)butyl]-1,3,4-thiadiazol-2-yl]-2-phenylacetamide
-
-
N-[5-[4-(5-amino-1,3,4-thiadiazol-2-yl)butyl]-1,3,4-thiadiazol-2-yl]-2-phenylpropanamide
-
-
N-[5-[4-(5-amino-1,3,4-thiadiazol-2-yl)butyl]-1,3,4-thiadiazol-2-yl]-3-phenylpropanamide
-
-
N-[5-[4-(5-amino-1,3,4-thiadiazol-2-yl)butyl]-1,3,4-thiadiazol-2-yl]benzamide
-
-
N-[5-[4-(5-amino-1,3,4-thiadiazol-2-yl)butyl]-1,3-thiazol-2-yl]-2-phenylacetamide
-
-
Na2SO4
-
glutaminase I and II
NaCIO4
-
0.3 M, 25% inhibition
NaF
-
inhibition to a variable extent
NaH2PO4
-
0.3 M, complete inhibition
NaI
-
above 0.3 M
NaN3
-
complete inhibition at 1 mM
NaNO3
-
0.3 M, 15% inhibition
Ngamma,Ngamma-diethyl-L-glutamine
-
-
Ngamma,Ngamma-dimethyl-L-glutamine
-
-
Ngamma-ethyl-L-glutamine
-
-
Ngamma-methyl-L-glutamine
-
-
nitidine
-
-
nitrite
-
0.5 M, complete inhibition
norsanguinarine
-
-
O-(diazoacetyl)-L-serine
-
-
p-benzoquinone
-
-
p-chloromercuribenzoate
-
p-chloromercuribenzoic acid
complete inhibition at 10 mM
p-mercuribenzoate
Pb2+
69.27% residual activity at 100 mM
phenylarsonic acid
-
causes a decrease in GAC levels
phenylmethylarsinic acid
-
causes a decrease in GAC levels
protein BNIP-H
i.e. Caytaxin or brain-specific BNIP-2-homology protein, encoded by gene ATCAY, important in neuromal function, inhibits the enzyme and alters its steady-state kinetics, relocalises glutaminase to neurite terminals and reduces glutamate levels in vivo, effects on glutamate levels in overexpressing cell lines, e.g. murine Neuro2A cells or rat PC-12 cells, or in female rat brain, detailed overview
-
pyruvate
R(-)-apocodeine
-
-
-
R(-)-propylnorapomorphine
-
-
Rose bengal
-
0.01%, irreversible inactivation
sanguinarine
-
-
succinate
-
enzyme from mesenteric lymph nodes
Tris
-
0.5 M, complete inhibition
Triton X-100
-
-
Zn2+
82.12% residual activity at 100 mM
ZnCl2
-
7% inhibition at 1 mM
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,10-phenanthroline
-
slight activation
2-mercaptoethanol
138.22% activity at 100 mM
angiotensin II
-
activates
citrate
-
enhances activity
CTP
-
activates enzyme from mesenteric lymph nodes
cysteine
128.15% activity at 100 mM
D-fructose 6-phosphate
-
activates enzyme from mesenteric lymph nodes
D-glucose 6-phosphate
-
activates enzyme from mesenteric lymph nodes
dithiothreitol
EDTA
-
slight activation
Epidermal growth factor
-
kidney-type glutaminase activity in cells is stimulated by EGF
glucagon
-
activates
glutathione
129.32% activity at 100 mM
glyoxylate
-
50 mM, increasing enzyme activity by 30%
GTP
-
activates enzyme from mesenteric lymph nodes
HCO3-
-
activates
ITP
-
activates enzyme from mesenteric lymph nodes
L-ascorbic acid
128.23% activity at 100 mM
L-glutamine
enhanced enzyme activity in jejunal mucosa
Lactate
-
enhances activity
Leu
-
activates enzyme from mesenteric lymph nodes, 50% activation at 0.6 mM
malate
-
enhances activity
oxaloacetate
-
50 mM, increasing enzyme activity by 30%
phosphate
phosphoenolpyruvate
-
activates enzyme from mesenteric lymph nodes, 50% activation at 0.2 mM
sulfate
Tris
activates Mglu by approximately 6fold at pH 7.5
additional information
-
strong stimulation of glutaminase subunit TrpG activity by the associated synthase subunit TrpE within the glutamine amidotransferase, GATase, enzyme complex
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.195
2-oxo-glutaramate
-
pH 8.5, 30C
0.003 - 0.017
2-oxo-succinamate
0.012
5-methoxy-2,5-dioxopentanoic acid
-
pH 7.2, 30C
6.7
D-gamma-Gln-methylester
-
glutaminase B
83
D-glutamine
-
pH 9.0, at 37C, H2O as co-substrate
0.92
D-Theanine
-
glutaminase B
50
gamma-ethyl glutamate
-
-
12
gamma-glutamyl hydrazide
-
-
15
gamma-glutamyl hydroxamate
-
pH 9.0, at 37C, NH2OH as co-substrate
3.3
gamma-glutamyl methylamide
-
-
64
gamma-methyl glutamate
-
-
23
gamma-thioethyl glutamate
-
-
10
gamma-thiomethyl glutamate
-
-
0.42 - 21
Gln
2.9
Glu
-
-
4.8 - 109.5
glutamine
1.27 - 1.48
Glutaramate
4.8 - 24
L-Asn
200
L-gamma-Gln-L-Ala
-
glutaminase B
-
2.1
L-gamma-Gln-methyl ester
-
glutaminase B
2.6 - 6.5
L-Gln
500
L-Glutamic acid
-
pH 9.0, at 37C, NH2OH as co-substrate
0.0053 - 460
L-glutamine
0.71
L-Theanine
-
glutaminase B
0.14 - 0.23
succinamate
additional information
L-glutamate
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
17.5
2-oxo-glutaramate
Mus musculus
-
pH 8.5, 30C
0.87 - 1.15
2-oxo-succinamate
134.5
5-methoxy-2,5-dioxopentanoic acid
Mus musculus
-
pH 7.2, 30C
36
gamma-ethyl glutamate
Escherichia coli
-
-
14
gamma-glutamyl hydrazide
Escherichia coli
-
-
296
gamma-glutamyl methoxyamide
Escherichia coli
-
-
8
gamma-glutamyl methylamide
Escherichia coli
-
-
212
gamma-glutamyl-hydroxamate
Escherichia coli
-
-
645
gamma-methyl glutamate
Escherichia coli
-
-
300
gamma-thioethyl glutamate
Escherichia coli
-
-
1260
gamma-thiomethyl glutamate
Escherichia coli
-
-
1270
Gln
Escherichia coli
-
-
5080
Glu
Escherichia coli
-
-
4.1 - 8.8
Glutaramate
4790
Gly-Gln
Aspergillus sojae
-
at pH 9.0 and 50C
1606
L-asparagine
Aspergillus sojae
-
at pH 9.0 and 50C
0.222 - 6249
L-glutamine
2 - 2.8
succinamate
additional information
additional information
Escherichia coli
-
effect of pH on turnover number
-
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
89.7
2-oxo-glutaramate
Mus musculus
-
pH 8.5, 30C
42224
51.2 - 385
2-oxo-succinamate
11200
5-methoxy-2,5-dioxopentanoic acid
Mus musculus
-
pH 7.2, 30C
42223
2.8 - 6.9
Glutaramate
0.63 - 47
L-glutamine
8.7 - 20
succinamate
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2.7
2-oxoglutarate
-
pH 7.0, at 37C
3.5
ampicillin
competitive inhibitor
0.00232
apomorphine
-
pH and temperature not specified in the publication
0.003
bis-2-(5-phenylacetamido-1,2,4-thiadiazol-2-yl)ethyl sulfide
-
-
0.000125
bis-2-(5-phenylacetimido-1,2,4-thiadiazol-2-yl)ethyl sulfide
-
pH and temperature not specified in the publication
0.00027
chelerythrine
-
pH and temperature not specified in the publication
0.000015
ebselen
-
pH and temperature not specified in the publication
2.95
Ngamma,Ngamma-diethyl-L-glutamine
-
37C, pH 7.5
2.64
Ngamma,Ngamma-dimethyl-L-glutamine
-
37C, pH 7.5
1.58
Ngamma-ethyl-L-glutamine
-
37C, pH 7.5
1.11
Ngamma-methyl-L-glutamine
-
37C, pH 7.5
0.7
pyruvate
-
pH 7.0, at 37C
additional information
L-glutamate
-
39.0 mol/l, pH and temperature not specified in this publication
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0231 - 0.05
(2R)-1-(2-formyl-3,6-dihydroxy-5-methoxycyclohexa-1,4-dien-1-yl)tridecan-2-yl acetate
0.0251 - 0.05
(2R)-1-(2-hydroxy-5-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)pentadecan-2-yl acetate
0.05 - 0.5
(2R)-1-(2-hydroxy-5-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tridecan-2-yl acetate
0.00026 - 0.0029
(2R)-1-(3,6-dihydroxy-5-methoxycyclohexa-1,4-dien-1-yl)tridecan-2-yl acetate
0.00028 - 0.0021
(2R)-1-(5-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)pentadecan-2-yl acetate
0.00029 - 0.0039
(2R)-1-(5-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)tridecan-2-yl acetate
0.0057 - 0.069
(2R)-1-[3-(acetyloxy)-6-hydroxy-5-methoxycyclohexa-1,4-dien-1-yl]pentadecan-2-yl acetate
0.0317 - 0.05
(2R)-1-[3-(acetyloxy)-6-hydroxy-5-methoxycyclohexa-1,4-dien-1-yl]tridecan-2-yl acetate
0.05 - 0.0527
(2S)-1-(5-methoxycyclohexa-1,4-dien-1-yl)heptan-2-ol
0.5
2-hydroxy-5-methoxy-3-tridecylcyclohexa-2,5-diene-1,4-dione
Homo sapiens
-
IC50 above 0.05 mM, isoform KGA, at pH 8.6 and 37C
0.05 - 0.5
2-methoxy-6-pentadecylcyclohexa-2,5-diene-1,4-dione
0.0325 - 0.5
2-methoxy-6-tridecylcyclohexa-2,5-diene-1,4-dione
0.0027 - 0.0769
2-methyl-5-[(7Z)-pentadec-7-en-1-yl]cyclohexa-1,4-diene-1,3-diol
0.05 - 0.0598
2-methyl-5-[(7Z)-tridec-7-en-1-yl]cyclohexa-1,4-diene-1,3-diol
0.1
2-phenyl isoindolin-1-one
Mus musculus
-
IC50 above 0.1 mM, pH and temperature not specified in the publication
-
0.02
2-phenylbenzo[d] isoxazol-3(2H)-one
Mus musculus
-
pH and temperature not specified in the publication
-
0.0076 - 0.0524
3-[(2S)-2-hydroxypentadecyl]-5-methoxycyclohexa-2,5-dien-1-ol
0.0047 - 0.041
4-hydroxy-2-methoxy-6-(2-oxopentadecyl)cyclohexa-2,5-dien-1-yl acetate
0.1
5,5'-(sulfanediyldiethane-2,1-diyl)bis(1,3,4-thiadiazol-2-amine)
Homo sapiens
-
in 45 mM phosphate buffer (pH 8.2), at 22C
0.0031 - 0.0139
5-[(6Z)-13-(3,5-dihydroxy-4-methylcyclohexa-1,4-dien-1-yl)tridec-6-en-1-yl]-2-methylbenzene-1,3-diol
0.0021 - 0.0117
5-[(6Z)-13-(3,5-dihydroxy-4-methylcyclohexa-1,4-dien-1-yl)tridec-6-en-1-yl]benzene-1,3-diol
0.0029 - 0.0096
5-[(6Z)-13-(3-hydroxy-5-methoxycyclohexa-1,4-dien-1-yl)tridec-6-en-1-yl]benzene-1,3-diol
0.0025 - 0.0367
5-[(7Z)-13-(3-hydroxy-5-methoxyphenyl)tridec-7-en-1-yl]-2-methylcyclohexa-1,4-diene-1,3-diol
0.0023 - 0.07
5-[(7Z)-15-(3-hydroxy-5-methoxyphenyl)pentadec-7-en-1-yl]-2-methylcyclohexa-1,4-diene-1,3-diol
0.0029 - 0.073
5-[(7Z)-pentadec-7-en-1-yl]cyclohexa-1,4-diene-1,3-diol
0.0028 - 0.0765
5-[(7Z)-tridec-7-en-1-yl]cyclohexa-1,4-diene-1,3-diol
0.0029 - 0.0175
5-[(8Z)-15-(3,5-dihydroxy-4-methylcyclohexa-1,4-dien-1-yl)pentadec-8-en-1-yl]-2-methylbenzene-1,3-diol
0.0023 - 0.0119
5-[(8Z)-15-(3,5-dihydroxy-4-methylcyclohexa-1,4-dien-1-yl)pentadec-8-en-1-yl]benzene-1,3-diol
0.0029 - 0.0134
5-[(8Z)-15-(3-hydroxy-5-methoxycyclohexa-1,4-dien-1-yl)pentadec-8-en-1-yl]benzene-1,3-diol
0.0028 - 0.0144
5-[14-(3-hydroxy-5-methoxycyclohexa-1,4-dien-1-yl)tetradecyl]benzene-1,3-diol
0.0014
5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]-N-[2-(4-phenylpiperidin-1-yl)ethyl]pentanamide
Homo sapiens
-
in 45 mM phosphate buffer (pH 8.2), at 22C
0.01
5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]-N-[2-(piperidin-1-yl)ethyl]pentanamide
Homo sapiens
-
IC50 above 0.1 mM, in 45 mM phosphate buffer (pH 8.2), at 22C
0.0046
5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]-N-[2-(pyrrolidin-1-yl)ethyl]pentanamide
Homo sapiens
-
in 45 mM phosphate buffer (pH 8.2), at 22C
0.1
5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]-N-[4-(trifluoromethyl)benzyl]pentanamide
Homo sapiens
-
IC50 above 0.1 mM, in 45 mM phosphate buffer (pH 8.2), at 22C
0.0599
6-diazo-5-oxo-L-norleucine
Homo sapiens
-
isoform KGA, at pH 8.6 and 37C
0.0006
apomorphine
Mus musculus
-
pH and temperature not specified in the publication
0.1
Berberine
Mus musculus
-
IC50 above 0.1 mM, pH and temperature not specified in the publication
0.00006 - 0.1
bis-2-(5-phenylacetimido-1,2,4,thiadiazol-2-yl)ethyl sulfide
0.00008 - 0.0636
bis-2-(5-phenylacetimido-1,2,4-thiadiazol-2-yl) ethyl sulfide
0.00003
chelerythrine
Mus musculus
-
pH and temperature not specified in the publication
0.000009
ebselen
Mus musculus
-
pH and temperature not specified in the publication
0.2 - 5.5
Mg2+
0.1 - 1.3
Mn2+
0.0033
N,N'-[sulfanediylbis(ethane-2,1-diyl-1,3,4-thiadiazole-5,2-diyl)]bis(2-phenylacetamide)
Homo sapiens
-
in 45 mM phosphate buffer (pH 8.2), at 22C
0.1
N-(2-aminoethyl)-5-[5-[(phenylacetyl)amino]-1,3,4-thiadiazol-2-yl]pentanamide