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Synthesis of D- and L-5-Oxaproline and of a New Captopril Analogue

✍ Scribed by Andrea Vasella; Robert Voeffray; Janos Pless; René Huguenin

Book ID
102858773
Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
823 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The 1,3‐dipolar cycloaddition of the C‐t‐butyloxycarbonyl‐N‐mannosyl‐nitrone 5, formed in situ from the partially protected D‐mannose‐oxime 3 and the glyoxylate 4, to ethylene gave preferentially the (3__S__)‐N‐glycosyl‐isoxazolidine 6 which was transformed into the 3‐isoxazolidine‐carboxylate (L‐5‐oxaproline ester) 12 and into some derivatives thereof. The (S)‐configuration of 12 was proved by chemical correlation with a derivative of L‐asparagine. The D‐5‐oxaproline ester was obtained from the corresponding N‐ribosyl‐nitrone 24. Two protected dipeptides containing either C‐terminal‐ (28) or N‐terminal‐5‐oxaproline (= Opro) (30) were synthesized. Starting from 12, the analogue 1 of captopril® (2) was prepared and its activity as an inhibitor of the angiotensin‐converting‐enzyme (ACE) was examined.

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