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Synthesis of isotopically labelled amino acids
Author(s) -
Rees David O.,
Bushby Nick,
Harding John R.,
Song Chuanjun,
Willis Christine L.
Publication year - 2007
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.1301
Subject(s) - chemistry , amino acid , enantioselective synthesis , racemization , alkene , yield (engineering) , bromide , decarboxylation , stereochemistry , enantiomer , stereocenter , hydrolysis , cleavage (geology) , organic chemistry , catalysis , biochemistry , materials science , geotechnical engineering , fracture (geology) , engineering , metallurgy
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.