Methods for the Synthesis of L-Leucine Selectively Labelled with Carbon-13 or Deuterium in either Diastereotopic Methyl Group

NM Kelly, RG Reid, CL Willis, PL Winton

Index: Kelly; Kelly, Nicholas M.; Reid; Gordon Reid; Willis; Willis, Christine L.; Winton; Winton, Peter L. Tetrahedron Letters, 1995 , vol. 36, # 45 p. 8315 - 8318

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Citation Number: 18

Abstract

A versatile approach is described for the enantioselective synthesis of 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 amination of the ketone catalysed by leucine dehydrogenase. This strategy is applied to the total synthesis of (2S. 4R)-[5.5. 5-D3]-leucine using CD3I as the source of deuterium.