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Substrate Report for: D-Phenylglycine

Name Class
D-PhenylglycineOther_Name (5)
Chemical_Nomenclature(2R)-2-amino-2-phenylacetic acid
FormulaC8H9NO2
CAS_number875-74-1
MW151.16
PaperBarends_2006_J.Biol.Chem_281_5804
Paye_2018_Anal.Biochem_549_80
Blum_2010_J.Mol.Catal.B.Enzym_67_21
Structure2B4K
CommentSynthesis of antibiotics is catalyzed by AEHs. The enzyme is acylated by an activated acyl compound, e.g. an ester (d-phenylglycine methyl ester). The resulting acyl enzyme can be hydrolyzed, resulting in a carboxylic acid. Alternatively, the acyl enzyme may be aminolyzed by an amino-beta-lactam (eg 7-amino-desacetoxycephalosporanic acid is (7-ADCA)), resulting in the desired antibiotic. The product (D-Phenylglycine) may also react with free enzyme to form acyl enzyme that can be hydrolyzed.
Gene_locusacepa-AEHA
xanax-GAA
CID70134
FamilyCocaine_esterase
InChIKeyZGUNAGUHMKGQNY-SSDOTTSWSA-N
CanonicalSMILESC1=CC=C(C=C1)C(C(=O)O)N
InChIInChI=1S/C8H9NO2/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7H,9H2,(H,10,11)/t7-/m1/s1

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Mail to: Nicolas Lenfant, Thierry Hotelier, Yves Bourne, Pascale Marchot and Arnaud Chatonnet.
Please cite: Lenfant 2013 Nucleic.Acids.Res. or Marchot Chatonnet 2012 Prot.Pept Lett.
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