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Synthesis of optically active deuterium labelled serine and glycylserine derivatives

✍ Scribed by J. Kovacs; G. Jham; K. Y. Hui

Publisher
John Wiley and Sons
Year
1982
Tongue
French
Weight
445 KB
Volume
19
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Optically active α‐deuterated serine dipeptide active ester derivatives were prepared to study the racemization mechanism. N‐Acetyl‐O‐benzyl‐DL‐serine, 1, was converted to 5(4H)‐oxazolone 2 and deuterated with CH~3~‐COOD in α‐position. 5(4^2^H)‐Oxazolone 3 was converted to Z‐(α^2^H)‐L‐Ser(Bzl)‐OHThe following abbreviations are used: benzyloxycarbonyl = Z; tert‐butyloxycarbonyl = Boc; benzyl = Bzl; pentachlorophenyl = Pcp; dicyclohexylcarbodiimide = DCC; dicyclohexylurea = DCU, tetrahydrofuran = PHF; thin layer chromatography = TLC

7, after opening the 5(4^2^H)‐oxazolone ring with D~2~O, removal of the N‐acetyl group, treatment with carbobenzoxy chloride and resolution with (+)‐α‐phenylethylamine. Pentachlorophenyl ester 8 of 7 was converted to Z‐Gly‐(α^2^H)‐L‐Ser(Bzl)‐OPcp, 10, after removal of carbobenzoxy group by catalytic hydrogenation. The deuterium content of the intermediates was determined by mass spectrometry.

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