Tetrahedron p. 7127 - 7136 (1996)
Update date:2022-08-04
Topics: Enantiomer NMR spectroscopy Chiral center Organocatalysis (S)-aspartate semi-aldehyde Diastereomer
Coulter, Carolyn V.
Gerrard, Juliet A.
Kraunsoe, James A. E.
Moore, Deborah J.
Pratt, Andrew J.
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.
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