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Enzymatic synthesis of specifically 2H-labelled L-glutamic acids and 2H-, 15N-, 13C-labelled L-glutamines on a preparative scale

✍ Scribed by A. Ogrel; I. A. Vasilenko; J. Lugtenburg; J. Raap

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
707 KB
Volume
113
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

In this paper we report the preparation of specifically ^2^H‐labelled L‐glutamic acids and ^2^H‐, ^15^N‐, ^13^C‐labelled L‐glutamines on the gram scale. The products obtained have high isotope enrichment (>98%) and high optical purity. The synthetic schemes allow the specific isotope enrichment of every H, C, and N position or any combination of positions. (2‐^2^H)‐L‐Glutamic acid was synthesized by enantioselective enzymatic conversion of 2‐oxoglutaric acid using glutamate dehydrogenase (GDH, E.C. 1.4.1.3.), alcohol dehydrogenase (ADH, E.C. 1.1.1.1.) and (^2^H~6~)ethanol. (3,3‐^2^H~2~)‐L‐Glutamic acid was prepared by enzymatic conversion of 2‐oxo‐3,3‐di‐deuteroglutaric acid which was easily obtained from 2‐oxoglutaric acid by an isotope exchange reaction in ^2^H~2~O at pH 13.0. (4,4‐^2^H~2~)‐L‐Glutamic acid was obtained by chemical exchange in 20% ^2^HCl. Four different isotopomers of L‐glutamine [(2‐^2^H)‐, (3,3‐^2^H~2~)‐, (4,4‐^2^H~2~)‐, and (5‐^13^C)‐L‐Gln] were synthesized by the enantioselective conversion of isotopically labelled L‐glutamic acids using glutamine synthetase (GS, E.C. 6.3.1.2.). The amide group of glutamine was labelled with ^15^N using ^15^NH~4~Cl in the enzymatic reaction. The labelled L‐glutamic acids and L‐glutamines were characterized by ^1^H‐NMR, ^13^C‐NMR and mass spectrometry.

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