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Chemical Compound Review

Phenylglycine     (2R)-2-amino-2-phenyl-ethanoic acid

Synonyms: D-PHG-OH, H-D-PHG-OH, CHEMBL1403, PubChem11005, SureCN159420, ...
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Disease relevance of D-PHENYLGLYCINE


High impact information on D-PHENYLGLYCINE

  • The crystal structures of the native enzyme, both unliganded and in complex with the hydrolysis product D-phenylglycine are reported, as well as the structures of an inactive mutant (S205A) complexed with the substrate ampicillin, and an active site mutant (Y206A) with an increased tendency to catalyze antibiotic production rather than hydrolysis [4].
  • The nitrile hydratase (from R. rhodochrous MAWE)-catalyzed hydration of D-phenylglycine nitrile to the corresponding amide was combined with the penicillin G acylase (penicillin amidohydrolase, E.C. acylation of 7-ADCA with the in situ-formed amide to afford a two-step, one-pot synthesis of cephalexin [5].
  • Reproducibility of the separation of astaxanthin stereoisomers on Pirkle covalent L-leucine and D-phenylglycine columns [6].

Biological context of D-PHENYLGLYCINE

  • Penicillin G acylase (PGA) is exploited for producing pure D-phenylglycine from a racemate mixture, via an acylation reaction onto a cosubstrate, the ester methyl-4-hydroxyphenyl acetate [7].

Associations of D-PHENYLGLYCINE with other chemical compounds

  • Immobilized Candida antarctica lipase B (Novozym 435)-catalyzed enantioselective hydrolysis of D,L-phenylglycine methyl ester to enatiopure D-phenylglycine was successfully conducted in the systems with ionic liquids (ILs) [8].


  1. Crystallization and preliminary X-ray crystallographic analysis of d-phenylglycine aminotransferase from Pseudomonas stutzeri ST201. Kongsaeree, P., Samanchart, C., Laowanapiban, P., Wiyakrutta, S., Meevootisom, V. Acta Crystallogr. D Biol. Crystallogr. (2003) [Pubmed]
  2. Microencapsulation and modification of synthetic peptides of food proteins reduces the blood pressure of spontaneously hypertensive rats. Chen, T.L., Lo, Y.C., Hu, W.T., Wu, M.C., Chen, S.T., Chang, H.M. J. Agric. Food Chem. (2003) [Pubmed]
  3. Antimicrobial activity of N-phthaloylamino acid hydroxamates. Matijević-Sosa, J., Cvetnić, Z. Acta pharmaceutica (Zagreb, Croatia) (2005) [Pubmed]
  4. Acetobacter turbidans alpha-amino acid ester hydrolase: how a single mutation improves an antibiotic-producing enzyme. Barends, T.R., Polderman-Tijmes, J.J., Jekel, P.A., Williams, C., Wybenga, G., Janssen, D.B., Dijkstra, B.W. J. Biol. Chem. (2006) [Pubmed]
  5. A two-step, one-pot enzymatic synthesis of cephalexin from D-phenylglycine nitrile. Wegman, M.A., van Langen, L.M., van Rantwijk, F., Sheldon, R.A. Biotechnol. Bioeng. (2002) [Pubmed]
  6. Reproducibility of the separation of astaxanthin stereoisomers on Pirkle covalent L-leucine and D-phenylglycine columns. Abu-Lafi, S., Turujman, S.A. Journal of chromatography. A. (1999) [Pubmed]
  7. Production of D-phenylglycine from racemic (D,L)-phenylglycine via isoelectrically-trapped penicillin G acylase. Bossi, A., Cretich, M., Righetti, P.G. Biotechnol. Bioeng. (1998) [Pubmed]
  8. Efficient enantioselective hydrolysis of D,L-phenylglycine methyl ester catalyzed by immobilized Candida antarctica lipase B in ionic liquid containing systems. Lou, W.Y., Zong, M.H., Liu, Y.Y., Wang, J.F. J. Biotechnol. (2006) [Pubmed]
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