Rhea - reaction knowledgebase

Enzymes

Enzyme class ^help_outline	EC 3.1.1.43 alpha-amino-acid esterase
GO Molecular Function ^help_outline	GO:0047658 alpha-amino-acid esterase activity

Reaction participants Show >> << Hide

Name ^help_outline an α-amino acid ester Identifier CHEBI:83410 Charge 1 Formula C2H4NO2R2 SMILES^help_outline [NH3+]C([*])C(=O)O[*] 2D coordinates Mol file for the small molecule Search links Involved in 4 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline H₂O Identifier CHEBI:15377 (Beilstein: 3587155; CAS: 7732-18-5) ^help_outline Charge 0 Formula H2O InChIKey^help_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILES^help_outline [H]O[H] 2D coordinates Mol file for the small molecule Search links Involved in 6,048 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline an alcohol Identifier CHEBI:30879 Charge 0 Formula HOR SMILES^help_outline O[*] 2D coordinates Mol file for the small molecule Search links Involved in 1,506 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline an α-amino acid Identifier CHEBI:78608 Charge 0 Formula C2H4NO2R SMILES^help_outline [NH3+]C([*])C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 341 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline H⁺ Identifier CHEBI:15378 Charge 1 Formula H InChIKey^help_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILES^help_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,176 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule

Cross-references

	RHEA:17241	RHEA:17242	RHEA:17243	RHEA:17244
Reaction direction	undefined	left-to-right	right-to-left	bidirectional
UniProtKB ^help_outline
EC numbers ^help_outline	3.1.1.43
Gene Ontology ^help_outline	GO:0047658
KEGG ^help_outline				R04191
MetaCyc ^help_outline		ALPHA-AMINO-ACID-ESTERASE-RXN

Publications

Substrate specificity of an alpha-amino acid ester hydrolase produced by Acetobacter turbidans A.T.C.C. 9325.

Takahashi T., Yamazaki Y., Kato K.

A partially purified preparation of an alpha-amino acid ester hydrolase was obtained from Acetobacter turbidans A.T.C.C. 9325, which catalyses synthesis of 7-(d-alpha-amino-alpha-phenylacetamido)-3-cephem-3-methyl-4-carboxylic acid (cephalexin) from methyl d-alpha-aminophenylacetate and 7-amino-3- ... >> More

A partially purified preparation of an alpha-amino acid ester hydrolase was obtained from Acetobacter turbidans A.T.C.C. 9325, which catalyses synthesis of 7-(d-alpha-amino-alpha-phenylacetamido)-3-cephem-3-methyl-4-carboxylic acid (cephalexin) from methyl d-alpha-aminophenylacetate and 7-amino-3-deacetoxycephalosporanic acid. The enzyme preparation catalysed both cephalosprin synthesis from 7-amino-3-deacetoxycephalosporanic acid and suitable amino acid esters (e.g. methyl d-alpha-aminophenylacetate, l-cysteine methyl ester, glycine ethyl ester, d-alanine methyl ester, methyl dl-alpha-aminoiso-butyrate, l-serine methyl ester, d-leucine methyl ester, l-methionine methyl ester) and the hydrolysis of such esters. The substrate specificity of the enzyme preparation for the hydrolysis closely paralleled the acyl-donor specificity for cephalosporin synthesis, even to the reaction rates. Only alpha-amino acid derivatives could act as acyl donors. The hydrogen atom on the alpha-carbon atom was not always required by acyl donors. The hydrolysis rate was markedly diminished by adding 7-amino-3-deacetoxycephalosporanic acid to reaction mixtures, but no effect on the total reaction rate (the hydrolysis rate plus synthesis rate) was observed with various concentrations of 7-amino-3-deacetoxycephalosporanic acid. Both the hydrolytic and the synthetic activities of the enzyme preparation were inhibited by high concentrations of some acyl donors (e.g. methyl d-alpha-aminophenylacetate, ethyl d-alpha-aminophenylacetate). The enzyme preparation hydrolysed alpha-amino acid esters much more easily than alpha-amino acid derivatives with an acid-amide bond. << Less

Biochem J 137:497-503(1974) [PubMed] [EuropePMC]

Comments

Published in: Kato, K., Kawahara, K., Takahashi, T. and Kakinuma, A. Purification of an alpha-amino acid ester hydrolase from Xanthomonas citri. Agric. Biol. Chem. 44 (1980) 1069–1074. Kato, K., Kawahara, K., Takahashi, T. and Kakinuma, A. Substrate specificity of an alpha-amino acid ester hydrolase from Xanthomonas citri. Agric. Biol. Chem. 44 (1980) 1075–1081.