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Information on EC 3.5.1.3 - omega-amidase
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3.5.1.3 omega-amidaseIUBMB Comments
Acts on glutaramate, succinamate and their 2-oxo derivatives.
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Word Map
- 3.5.1.3
- alpha-ketoglutaramate
- asparagine
-
transamination
- ammonia
- oxaloacetate
- succinamate
- glutaminase
-
transamidase
- analysis
- medicine
- biotechnology
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Synonyms
omega-amidase, omega-amidase/nit2, omega-amidodicarboxylate amidohydrolase, nitrilase-like protein 2, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
alpha-keto acid omega-amidase
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alpha-keto acid-omega-amidase
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amidase, omega
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dicarboxylate omega-amidase
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NIT2
Nit2/omega-amidase
nitrilase-like protein 2
omega-amidase
omega-amidase/Nit2
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omega-amidase has been shown to be identical to Nit2, a putative tumor suppressor protein
omega-amido dicarboxylate amidohydrolase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a monoamide of a dicarboxylate + H2O = a dicarboxylate + NH3
mechanism
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a monoamide of a dicarboxylate + H2O = a dicarboxylate + NH3
kinetic evidence for an acyl-enzyme intermediate
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a monoamide of a dicarboxylate + H2O = a dicarboxylate + NH3
two-step mechanism
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a monoamide of a dicarboxylate + H2O = a dicarboxylate + NH3
acyl-enzyme mechanism
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a monoamide of a dicarboxylate + H2O = a dicarboxylate + NH3
catalytic sequence involves two steps and an acyl-enzyme intermediate
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a monoamide of a dicarboxylate + H2O = a dicarboxylate + NH3
double displacement or ping-pong mechanism
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a monoamide of a dicarboxylate + H2O = a dicarboxylate + NH3
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydrolysis of peptide bond
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transamidation
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
omega-amidodicarboxylate amidohydrolase
Acts on glutaramate, succinamate and their 2-oxo derivatives.
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CAS REGISTRY NUMBER
COMMENTARY
9025-19-8
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
butyl glutarate + hydoxylamine
glutaramate + butanol
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hydroxaminolysis
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-
?
ethyl glutarate + hydoxylamine
glutaramate + ethanol
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hydroxaminolysis
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-
?
ethyl succinate + hydoxylamine
succinamate + ethanol
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hydroxaminolysis
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-
?
fumarate + hydroxylamine
fumaryl hydroxamate + H2O
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acyl transfer reaction
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-
?
gamma-monomethyl-2-oxoglutaramate + H2O
gamma-monomethyl-2-oxoglutarate + NH3
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tested at pH 7.2 and pH 8.5
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-
?
glutaramate + methanol
glutarate methyl ester + hydroxylamine
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methanolysis
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?
L-asparagine + hydroxylamine
L-asparaginyl hydroxamate + H2O
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amide transfer reaction
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-
?
L-phenylalanine amide + H2O
L-Phe + NH3
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poor substrate, 12% compared with alpha-ketoglutaramate
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-
?
methyl succinate + hydoxylamine
succinamate + methanol
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hydroxaminolysis
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?
p-methylphenyl glutarate + hydroxylamine
glutaramate + 4-methylphenol
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?
propyl glutarate + hydoxylamine
glutaramate + propanol
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hydroxaminolysis
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
the product of glutamine transamination, 2-oxoglutaramate, can be hydrolyzed by the enzyme omega-amidase to form and ammonia
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
the product of glutamine transamination, 2-oxoglutaramate, can be hydrolyzed by the enzyme omega-amidase to form and ammonia
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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alpha-ketoglutaramate
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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physiological function of omega-amidase might be hydrolysis or transfer of amide group of alpha-ketoglutarate
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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alpha-ketoglutaramate
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-
?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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alpha-ketoglutaramate
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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alpha-ketoglutaramate
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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the in vivo substrates are generated by transamination of glutamine and asparagine, respectively
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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alpha-ketoglutaramate
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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alpha-ketoglutaramate
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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the conserved Cys-Glu-Lys triad is involved in catalysis
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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sole substrate is the open-chain form of alpha-ketoglutaramate, not the cyclic form
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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alpha-ketoglutaramate
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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alpha-ketoglutaramate
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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alpha-ketoglutaramate
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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alpha-ketoglutaramate
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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alpha-ketoglutaramate
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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alpha-ketoglutaramate
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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alpha-ketoglutaramate
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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alpha-ketoglutaramate
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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the in vivo substrates are generated by transamination of glutamine and asparagine, respectively
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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enzyme activity measured in a 96-well plate format
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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alpha-ketoglutaramate
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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alpha-ketoglutaramate
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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glutamine transaminase and omega-amidase potentially act in tandem to close the methionine salvage cycle in bacteria and plants
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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alpha-ketoglutaramate
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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alpha-ketoglutaramate
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
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physiological function of omega-amidase might be hydrolysis or transfer of amide group of alpha-ketoglutarate
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?
2-oxoglutaramate + H2O
2-oxoglutarate + NH3
glutamine transaminase and omega-amidase potentially act in tandem to close the methionine salvage cycle in bacteria and plants
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?
2-oxoglutaramate + hydroxylamine
2-oxoglutaryl hydroxamate + NH3
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alpha-ketoglutaramate
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?
2-oxoglutaramate + hydroxylamine
2-oxoglutaryl hydroxamate + NH3
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no hydroxaminolysis of alpha-ketoglutaramate at pH 8
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?
2-oxosuccinamate + H2O
2-oxosuccinate + NH3
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alpha-ketosuccinamate
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?
2-oxosuccinamate + H2O
2-oxosuccinate + NH3
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no formation of hydroxamate from alpha-ketosuccinamate
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?
2-oxosuccinamate + H2O
oxaloacetate + NH3
the product of asparagine transamination, 2-oxosuccinamate, can be hydrolyzed by the enzyme omega-amidase to form oxaloacetate and ammonia
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?
2-oxosuccinamate + H2O
oxaloacetate + NH3
the product of asparagine transamination, 2-oxosuccinamate, can be hydrolyzed by the enzyme omega-amidase to form oxaloacetate and ammonia
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?
2-oxosuccinamate + H2O
oxaloacetate + NH3
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the in vivo substrates are generated by transamination of glutamine and asparagine, respectively
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?
2-oxosuccinamate + H2O
oxaloacetate + NH3
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the in vivo substrates are generated by transamination of glutamine and asparagine, respectively
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?
2-oxosuccinamate + H2O
oxaloacetate + NH3
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enzyme activity measured in a 96-well plate format
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?
delta-methyl 2-oxoglutarate + H2O
?
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delta-methyl alpha-ketoglutarate
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?
gamma-ethyl 2-oxoglutarate + H2O
?
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gamma-methyl alpha-ketoglutarate
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?
gamma-ethyl 2-oxoglutarate + methylamine
?
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gamma-ethyl alpha-ketoglutarate
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?
gamma-methyl 2-oxoglutarate + H2O
?
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gamma-methyl alpha-ketoglutarate
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?
gamma-methyl 2-oxoglutarate + methylamine
?
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transamidation, very poor
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?
glutaramate + hydroxylamine
glutaryl hydroxamate + NH3
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amidase activity, hydrolysis proceeds at a slower rate than formation of glutaryl hydroxamate in the presence of hydroxylamine
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?
glutaramate + hydroxylamine
glutaryl hydroxamate + NH3
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hydroxaminolysis
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?
glutarate + hydroxylamine
glutaryl hydroxamate
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at pH 5, not at pH 7
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?
glutarate + hydroxylamine
glutaryl hydroxamate
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acyl-transfer reaction
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?
malate + hydroxylamine
malyl hydroxamate + H2O
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acyl transfer reaction
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?
malate + hydroxylamine
malyl hydroxamate + H2O
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acyl transfer reaction
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?
methyl glutarate + hydoxylamine
glutaramate + methanol
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hydroxaminolysis
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?
N-methyl-2-oxoglutaramate + H2O
2-oxoglutarate + methylamine
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at a slow rate
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?
N-methyl-2-oxoglutaramate + H2O
2-oxoglutarate + methylamine
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N-methyl-alpha-ketoglutaramate
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?
succinamate + H2O
succinic acid + NH3
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amidase activity, hydrolysis proceeds at a slower rate than formation of succinyl hydroxamate in the presence of hydroxylamine
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?
succinamate + H2O
succinic acid + NH3
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amidase activity, hydrolysis proceeds at a slower rate than formation of succinyl hydroxamate in the presence of hydroxylamine
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?
succinamate + H2O
succinic acid + NH3
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amidase activity, hydrolysis proceeds at a slower rate than formation of succinyl hydroxamate in the presence of hydroxylamine
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?
succinamate + hydroxylamine
succinyl hydroxamate + NH3
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amide transfer reaction
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r
succinamate + hydroxylamine
succinyl hydroxamate + NH3
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hydroxaminolysis
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r
succinamate + hydroxylamine
succinyl hydroxamate + NH3
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catalyzes formation of hydroxamate much more rapidly than hydrolysis of the amide
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r
succinamate + hydroxylamine
succinyl hydroxamate + NH3
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amide transfer reaction
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r
succinamide + hydroxylamine
succinyl hydroxamate + ?
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amide transfer reaction
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r
succinamide + hydroxylamine
succinyl hydroxamate + ?
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amide transfer reaction
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r
succinate + hydroxylamine
succinyl hydroxamate + H2O
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very high substrate concentration required for acyl transfer reaction
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r
succinate + hydroxylamine
succinyl hydroxamate + H2O
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acyl transfer reaction
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r
succinate + hydroxylamine
succinyl hydroxamate + H2O
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at pH 5, not at pH 7
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r
succinate + hydroxylamine
succinyl hydroxamate + H2O
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very high substrate concentration required for acyl transfer reaction
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r
succinate + hydroxylamine
succinyl hydroxamate + H2O
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acyl transfer reaction
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r
succinyl hydroxamate + H2O
succinate + hydroxylamine
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r
additional information
?
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the recombinant omega-amidase is equally active with 2-oxosuccinamate, 2-oxoglutaramate and 2-hydroxysuccinamate
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?
additional information
?
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the recombinant omega-amidase is equally active with 2-oxosuccinamate, 2-oxoglutaramate and 2-hydroxysuccinamate
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?
additional information
?
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catalyzes several enzymatic reactions: amide transfer, acyl transfer, and amide hydrolysis, are consistent with acyl enzyme type of intermediate
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?
additional information
?
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glutamine, acetamide, acetate, propionate, aspartate and glutamate not or very poor substrates
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?
additional information
?
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catalyzes hydrolysis of dicarboxylic acid amides and the formation of hydroxamates from amides, amide transfer, of the corresponding acids, acyl transfer
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?
additional information
?
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no reaction with monocarboxylic acids
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?
additional information
?
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catalyzes several enzymatic reactions: amide transfer, acyl transfer, and amide hydrolysis, are consistent with acyl enzyme type of intermediate
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?
additional information
?
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glutamine, acetamide, acetate, propionate, aspartate and glutamate not or very poor substrates
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