Stereospecific labeling at α-position of phenylalanine and phenylglycine with amino acid racemase

Young Hee Lim, Tohru Yoshimura, Kenji Soda, Nobuyoshi Esaki

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Amino acid racemase with low substrate specificity (EC 5.1.1.10) purified from Pseudomonas putida ATCC17642 catalyzes the racemization of various amino acids but not that of aromatic and acidic amino acids. However, phenylalanine and phenylglycine underwent α-hydrogen exchange with deuterium from the solvent when incubated with the racemase in deuterium oxide. Each enantiomer of both α-deuterated phenylalanine and phenylglycine was produced stereospecifically with retention of the C2 configuration. This α-hydrogen exchange reaction is applicable to the production of α-deuterated phenylalanine and phenylglycine.

Original languageEnglish
Pages (from-to)400-402
Number of pages3
JournalJournal of Fermentation and Bioengineering
Volume86
Issue number4
DOIs
Publication statusPublished - 1998 Jan 1
Externally publishedYes

Fingerprint

Amino Acid Isomerases
Phenylalanine
Labeling
Amino acids
Hydrogen
Deuterium Oxide
Acidic Amino Acids
Racemases and Epimerases
Heavy water
Aromatic Amino Acids
Pseudomonas putida
Enantiomers
Deuterium
Substrate Specificity
Amino Acids
Substrates

Keywords

  • Amino acid racemase
  • Enzymatic labeling
  • Phenylalanine
  • Phenylglycine

ASJC Scopus subject areas

  • Biotechnology
  • Applied Microbiology and Biotechnology

Cite this

Stereospecific labeling at α-position of phenylalanine and phenylglycine with amino acid racemase. / Lim, Young Hee; Yoshimura, Tohru; Soda, Kenji; Esaki, Nobuyoshi.

In: Journal of Fermentation and Bioengineering, Vol. 86, No. 4, 01.01.1998, p. 400-402.

Research output: Contribution to journalArticle

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