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Stereoselective synthesis of L ‐[2,3,4,5‐D 4 ] ornithine
Author(s) -
Oba Makoto,
Ishihara Teruaki,
Satake Hiromi,
Nishiyama Kozaburo
Publication year - 2002
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.592
Subject(s) - chemistry , derivative (finance) , stereoselectivity , stereochemistry , catalysis , glycine , deuterium , ornithine , glutamic acid , lactone , amino acid , organic chemistry , biochemistry , physics , arginine , quantum mechanics , financial economics , economics
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.