Synthesis of regio-and stereoselectively deuterium-labelled derivatives of l-glutamate semialdehyde for studies on carbapenem biosynthesis

…, RB Hamed, ET Batchelar, JL Sorensen…

Index: Ducho, Christian; Hamed, Refaat B.; Batchelar, Edward T.; Sorensen, John L.; Odell, Barbara; Schofield, Christopher J. Organic and Biomolecular Chemistry, 2009 , vol. 7, # 13 p. 2770 - 2779

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Citation Number: 17

Abstract

L-Glutamate semialdehyde (L-GSA) is an intermediate in biosynthetic pathways including those leading to the carbapenem antibiotics. We describe studies on asymmetric deuteration or hydrogenation of appropriate didehydro-amino acid precursors for the stereoselective synthesis of C-2-and/or C-3-[2H]-labelled L-GSA suitable for use in mechanistic studies. Regioselective deuterium incorporation into the 5-position of L-GSA was achieved using a ...