Convenient synthesis of deuterated glutamic acid, proline and leucine via catalytic deuteration of unsaturated pyroglutamate derivatives

✍ Scribed by Makoto Oba; Kosuke Ohkuma; Hiroshi Hitokawa; Ayumi Shirai; Kozaburo Nishiyama

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: French
• Weight: 106 KB
• Volume: 49
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.1038

✦ Synopsis

Abstract

Novel 3,4‐didehydropyroglutamate derivatives, the key intermediates in this synthesis, were obtained from a protected pyroglutamate by the well‐known selenenylation‐oxidative deselenenylation method and were catalytically deuterated using a slow‐addition technique. The obtained deuterated pyroglutamates were converted to [3,4‐^2^H~2~]glutamic acid, [3,4,5‐^2^H~3~]proline, and [3,4,5,5,5‐^2^H~5~]leucine via an appropriate functional group interconversions followed by the standard deprotection procedure. Copyright © 2006 John Wiley & Sons, Ltd.