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

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

doi:10.1016/S0922-338X(99)89012-6

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 journal › Article › peer-review

3 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 language	English
Pages (from-to)	400-402
Number of pages	3
Journal	Journal of Fermentation and Bioengineering
Volume	86
Issue number	4
DOIs	https://doi.org/10.1016/S0922-338X(99)89012-6
Publication status	Published - 1998
Externally published	Yes

Keywords

Amino acid racemase
Enzymatic labeling
Phenylalanine
Phenylglycine

ASJC Scopus subject areas

Biotechnology
Applied Microbiology and Biotechnology

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10.1016/S0922-338X(99)89012-6

Cite this

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title = "Stereospecific labeling at α-position of phenylalanine and phenylglycine with amino acid racemase",

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.",

keywords = "Amino acid racemase, Enzymatic labeling, Phenylalanine, Phenylglycine",

author = "Lim, {Young Hee} and Tohru Yoshimura and Kenji Soda and Nobuyoshi Esaki",

year = "1998",

doi = "10.1016/S0922-338X(99)89012-6",

language = "English",

volume = "86",

pages = "400--402",

journal = "Journal of Bioscience and Bioengineering",

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TY - JOUR

T1 - Stereospecific labeling at α-position of phenylalanine and phenylglycine with amino acid racemase

AU - Lim, Young Hee

AU - Yoshimura, Tohru

AU - Soda, Kenji

AU - Esaki, Nobuyoshi

PY - 1998

Y1 - 1998

N2 - 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.

AB - 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.

KW - Amino acid racemase

KW - Enzymatic labeling

KW - Phenylalanine

KW - Phenylglycine

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DO - 10.1016/S0922-338X(99)89012-6

M3 - Article

AN - SCOPUS:0031738919

SN - 1389-1723

VL - 86

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EP - 402

JO - Journal of Bioscience and Bioengineering

JF - Journal of Bioscience and Bioengineering

IS - 4

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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