METHODS FOR THE SYNTHESIS OF L-LEUCINE SELECTIVELY LABELED WITH C-13 OR DEUTERIUM IN EITHER DIASTEREOTOPIC METHYL-GROUP

Authors
KELLY NM REID RG WILLIS CL WINTON PL
Citation
Nm. Kelly et al., METHODS FOR THE SYNTHESIS OF L-LEUCINE SELECTIVELY LABELED WITH C-13 OR DEUTERIUM IN EITHER DIASTEREOTOPIC METHYL-GROUP, Tetrahedron letters, 36(45), 1995, pp. 8315-8318
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
45
Year of publication
1995
Pages
8315 - 8318
Database
ISI
SICI code
0040-4039(1995)36:45<8315:MFTSOL>2.0.ZU;2-B
Abstract
A versatile approach is described for the enantioselective synthesis o f isotopically labelled L-leucine involving the preparation of 2-oxo-4 -methylpentanoic acid labelled selectively with carbon-13 or deuterium in either the pro-R or pro-S methyl group followed by a reductive ami nation of the ketone catalysed by leucine dehydrogenase. This strategy is applied to the total synthesis of (2S,4R)-[5,5,5-D-3]-leucine usin g CD3I as the source of deuterium.