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Substrate Report for: D-Phenylglycine

Synthesis 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.


General
Type
Chemical_Nomenclature (2R)-2-amino-2-phenylacetic acid
Canonical SMILES C1=CC=C(C=C1)C(C(=O)O)N
InChI InChI=1S/C8H9NO2/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7H,9H2,(H,10,11)/t7-/m1/s1
InChIKey ZGUNAGUHMKGQNY-SSDOTTSWSA-N
Other name(s) D-(-)-alpha-Phenylglycine ; D-2-Phenylglycine ; (R)-2-Amino-2-phenylacetic acid ; H-D-PHG-OH ; 2-phenyl-D-glycine
________________________________________________________________________________________________
MW|151.16
Formula|C8H9NO2
CAS_number|875-74-1
PubChem|70134
UniChem|ZGUNAGUHMKGQNY-SSDOTTSWSA-N
IUPHAR|
Wikipedia|

Target
Families | D-Phenylglycine ligand of proteins in family: Cocaine_esterase
Stucture | 1 structure: 2B4K: Acetobacter turbidans alpha-amino acid ester hydrolase complexed with phenylglycine
Protein | acepa-AEHA, xanax-GAA

References:
Search PubMed for references concerning: D-Phenylglycine
    Title: A high-throughput pH-based colorimetric assay: application focus on alpha/beta hydrolases
    Paye MF, Rose HB, Robbins JM, Yunda DA, Cho S, Bommarius AS
    Ref: Analytical Biochemistry, 549:80, 2018 : PubMed

            

    Title: Amino ester hydrolase from Xanthomonas campestris pv. campestris, ATCC 33913 for enzymatic synthesis of ampicillin
    Blum JK, Bommarius AS
    Ref: J Mol Catal B Enzym, 67:21, 2010 : PubMed

            

    Title: Acetobacter turbidans alpha-amino acid ester hydrolase: how a single mutation improves an antibiotic-producing enzyme
    Barends TR, Polderman-Tijmes JJ, Jekel PA, Williams C, Wybenga G, Janssen DB, Dijkstra BW
    Ref: Journal of Biological Chemistry, 281:5804, 2006 : PubMed