(S)-ASPARTATE SEMI-ALDEHYDE - SYNTHETIC AND STRUCTURAL STUDIES

We report a novel synthesis of (S)-aspartate semi-aldehyde, (S)-ASA, 1 , a key intermediate in the biosynthesis of lysine, based on hydrolysi s of an enol ether precursor, (S)-2-amino-4-methoxybut-3-enoic acid, 1 0. (S)-ASA is conveniently and quantitatively liberated from this stab le intermediate and can be used in biological studies directly, since methanol is the only side-product. Enzyme inhibition studies and chemi cal precedent imply a cyclic lactol structure might be significant; he teronuclear multibond coupling (HMBC) measurements, however, are consi stent with the hydrate being the predominant species in aqueous soluti on. Copyright (C) 1996 Published by Elsevier Science Ltd