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(R)-(+)-mandelamide + H2O
(R)-(+)-mandelate + NH3
-
-
-
-
?
(R)-(-)-mandelamide + H2O
(R)-(-)mandelate + NH3
(R)-2-aminophenylacetamide + H2O
(R)-2-aminophenylacetate + NH3
-
-
-
-
?
(R)-lactamide + H2O
(R)-lactate + NH3
-
low efficiency
-
-
?
(R)-mandelamide + H2O
(R)-mandelate + NH3
-
-
-
?
(R)-mandelamide + H2O
(R)-mandelic acid + ammonia
-
-
-
-
?
(R,S)-methyl mandelate + H2O
?
-
-
?
(S)-(+)-mandelamide + H2O
(S)-(+)-mandelate + NH3
(S)-2-aminophenylacetamide + H2O
(S)-2-aminophenylacetate + NH3
-
-
-
-
?
(S)-lactamide + H2O
(S)-lactate + NH3
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low efficiency
-
-
?
(S)-mandelamide + H2O
(S)-mandelate + NH3
-
-
-
?
(S)-mandelamide + H2O
(S)-mandelic acid + ammonia
-
-
-
-
?
2-cyclohexylacetamide + H2O
2-cyclohexylacetate + NH3
-
-
-
-
?
2-phenylacetamide + H2O
2-phenylacetate + NH3
-
-
-
-
?
2-phenylacetamide + H2O
?
-
-
?
3,4-dichloroisocoumarin + H2O
?
-
-
-
-
?
3-phenylpropionamide + H2O
3-phenylpropionate + NH3
-
-
-
-
?
3-phenylpropionamide + H2O
?
-
-
?
4-nitroacetanilide + H2O
?
-
-
-
?
4-nitrophenylacetamide + H2O
4-nitrophenol + acetamide
-
-
-
?
4-nitrophenylacetate + H2O
4-nitrophenol + acetate
-
-
-
?
4-nitrophenylcarbonate + H2O
4-nitrophenol + CO2
-
-
-
?
acetamide + H2O
acetate + NH3
-
-
-
-
?
butanamide + H2O
butanoate + NH3
-
-
-
-
?
caproate + H2O
caproamide + NH3
-
-
-
-
?
cyclohexanecarboxamide + H2O
cyclohexanecarboxylate + NH3
-
-
-
-
?
hexanoamide + H2O
?
-
-
?
methyl 4-nitrophenylcarbonate + H2O
?
-
-
-
?
methyl mandelate + H2O
?
-
-
-
?
N-benzyloxycarbonylglycinamide + H2O
?
-
-
-
?
N-methyl phenylacetamide + H2O
?
-
-
?
pentanamide + H2O
pentanoate + NH3
-
-
-
-
?
phenyl carbamate + H2O
?
-
-
-
?
phenylacetamide + H2O
phenylacetate + NH3
phenylmethylsulfonyl fluoride + H2O
?
-
-
-
-
?
propanamide + H2O
propanoate + NH3
-
-
-
-
?
R,S-mandelamide + H2O
mandelic acid + ammonia
-
-
?
additional information
?
-
(R)-(-)-mandelamide + H2O
(R)-(-)mandelate + NH3
-
-
-
?
(R)-(-)-mandelamide + H2O
(R)-(-)mandelate + NH3
-
-
-
?
(S)-(+)-mandelamide + H2O
(S)-(+)-mandelate + NH3
-
-
-
?
(S)-(+)-mandelamide + H2O
(S)-(+)-mandelate + NH3
-
-
-
?
(S)-(+)-mandelamide + H2O
(S)-(+)-mandelate + NH3
-
-
-
-
?
phenylacetamide + H2O
phenylacetate + NH3
-
-
-
-
?
phenylacetamide + H2O
phenylacetate + NH3
-
-
-
?
additional information
?
-
-
benzamide is not a substrate
-
-
?
additional information
?
-
the lack of reactivity of MAH with the corresponding ethyl ester confirms the very limited size of the MAH leaving group site. The reactivity of MAH with 4-nitrophenyl acetate and methyl 4-nitrophenyl carbonate, therefore, suggests formation of an inverse acyl-enzyme where the small acyl-group occupies the normal leaving group site. Both (R)- and (S)-mandelamide are excellent substrates for MAH, while the enzyme can hydrolyze phenylacetamide with even higher catalytic efficiency. Reaction scheme for interaction of substrates with MAH. Substrate specificity, overview. No activity with ethyl 4-nitrophenylacetate, phenyl carbamate, and N-benzyloxycarbonyl-glycinamide, poor activity with phenyl acetate, 4-nitrophenyl n-butyrate, and ethyl 4-nitrophenyl carbonate
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-