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Synthesis of isotopically labelled amino acids

✍ Scribed by David O. Rees; Nick Bushby; John R. Harding; Chuanjun Song; Christine L. Willis

Publisher
John Wiley and Sons
Year
2007
Tongue
French
Weight
93 KB
Volume
50
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

An efficient approach to the enantioselective synthesis of a series of amino acids from either bromoacetyl bromide or glycine is described using a [2,3]‐sigmatropic rearrangement to establish the stereogenic centre at C‐2 under mild conditions. Protected allylglycine 5 is a valuable building block to several amino acids e.g. hydrolytic cleavage of the auxiliary in 5 followed by deprotection gave L‐allylglycine in 92% yield whilst oxidative cleavage of the terminal alkene followed by deprotection gave L‐aspartic acid in 67% yield over the 2 steps. Furthermore alkene 5 may be converted to hydroxy ester 8 which is an intermediate for the synthesis of various amino acids including L‐lysine and L‐proline. Since the enantiomer of sultam 1 is commercially available, the analogous D‐amino acids may be synthesised. This chemistry is readily adapted for the incorporation of isotopic labels for example for the synthesis of [1,2‐^13^C~2~,^15^N]‐L‐homoserine 14. Copyright © 2007 John Wiley & Sons, Ltd.

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