SYNTHESIS OF (2S,4S)-5,5'-DIHYDROXY[5,5-H-2(2)]LEUCINE AND (2S,4R)-5,5'-DIHYDROXY[5,5-H-2(2)]LEUCINE BY 2 INDEPENDENT ROUTES

Authors
DURAND X HUDHOMME P KHAN JA YOUNG DW
Citation
X. Durand et al., SYNTHESIS OF (2S,4S)-5,5'-DIHYDROXY[5,5-H-2(2)]LEUCINE AND (2S,4R)-5,5'-DIHYDROXY[5,5-H-2(2)]LEUCINE BY 2 INDEPENDENT ROUTES, Journal of the Chemical Society. Perkin transactions. I, (11), 1996, pp. 1131-1139
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
11
Year of publication
1996
Pages
1131 - 1139
Database
ISI
SICI code
0300-922X(1996):11<1131:SO(A(>2.0.ZU;2-W
Abstract
In studies directed at discovering the absolute stereochemistry of the reaction catalysed by the enzyme glutamate gamma-carboxylase, two ind ependent stereoselective syntheses of (2S,4S)-5,5'-dihydroxy[5,5-H-2(2 )]leucine 4a and its (2S,4R)-diastereoisomer 4b have been developed. T he first synthesis uses (2S)-pyroglutamic acid as starting material an d provides (2S,4S)-5,5'-dihydroxy[-5,5-H-2(2)]leucine 4a, while the se cond starts with (2S,4R)-4-hydroxyproline and provides (2S,4R)-5,5'-di hydroxy[5,5-H-2(2)] leucine 4b.