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Determination of the erythro and threo configuration of the two diastereoisomeric 2-amino-3-mercaptobutyric acids by NMR spectroscopy of derived thiazolidines

✍ Scribed by S. Toppet; P. Claes; J. Hoogmartens

Publisher: John Wiley and Sons
Year: 1974
Tongue: English
Weight: 490 KB
Volume: 6
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1270060113

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✦ Synopsis

Abstract

A study of the ^1^H and ^13^C NMR spectra of the N‐formyl‐2,2,5‐trimethyl‐4‐carboxythiazolidines and the N‐formyl‐4‐carboxy‐5‐methylthiazolidines derived from the two diastereoisomeric 2‐amino‐3‐mercapto‐DL‐butyric acids, permits unambiguous assignment of the erythro and threo configuration of these amino acids. The spectra of the N‐formylthiazolidines, recorded in DMSO‐d~6~ solution, reveal the presence of two conformational isomers with a low rate of interconversion. The geometry around the carbon–nitrogen bond and correlated conformations of the 5‐membered ring in both forms are discussed.

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