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Stereoselective synthesis of L-[2,3,4,5-D4] ornithine

✍ Scribed by Makoto Oba; Teruaki Ishihara; Hiromi Satake; Kozaburo Nishiyama

Publisher: John Wiley and Sons
Year: 2002
Tongue: French
Weight: 100 KB
Volume: 45
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.592

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✦ Synopsis

Abstract

Synthesis of L‐[2,3,4,5‐D~4~]ornithine in which all of the diastereotopic hydrogens were stereoselectively labeled with deuterium was investigated. The chirally deuterated 3‐aminopropanal derivative, a key intermediate in this synthesis, was prepared by a catalytic deuteration of an unsaturated γ‐lactone derived for L‐glutamic acid followed by several functional group interconversions. Condensation of the obtained deuterium‐labeled 3‐aminopropanal derivative with a chiral glycine template afforded unsaturated ornithine. The dehydroornithine was then subjected to a catalytic deuteration followed by deprotection to give the L‐[2,3,4,5‐D~4~]ornithine. Copyright © 2002 John Wiley & Sons, Ltd.

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