(S)-aspartate semi-aldehyde: Synthetic and structural studies

Article abstract of DOI:10.1016/0040-4020(96)00330-4

We report a novel synthesis of (S)-aspartate semi-aldehyde, (S)-ASA, 1, a key intermediate in the biosynthesis of lysine, based on hydrolysis of an enol ether precursor, (S)-2-amino-4-methoxybut-3-enoic acid, 10, (S)-ASA is conveniently and quantitatively liberated from this stable intermediate and can be used in biological studies directly, since methanol is the only side-product. Enzyme inhibition studies and chemical precedent imply a cyclic lactol structure might be significant; heteronuclear multibond coupling (HMBC) measurements, however, are consistent with the hydrate being the predominant species in aqueous solution.