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An improved synthesis of (2S, 4S)- and (2S, 4R)-2-amino-4-methyldecanoic acids: assignment of the stereochemistry of culicinins

✍ Scribed by Wei Zhang; Ning Ding; Yingxia Li

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
205 KB
Volume
17
Category
Article
ISSN
1075-2617

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✦ Synopsis

Abstract

An improved synthesis of (2__S__, 4__S__)‐ and (2__S__, 4__R__)‐2‐amino‐4‐methyldecanoic acids was accomplished using a glutamate derivative as starting material and Evans' asymmetric alkylation as the decisive step. The NMR data of the two diastereomers were measured and compared with those of the natural product. As a result, the stereochemistry of this novel amino acid unit in culicinins was assigned as (2__S__, 4__R__). Copyright Β© 2011 European Peptide Society and John Wiley & Sons, Ltd.

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