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

Autor:	Carolyn V. Coulter, Deborah J. Moore, Juliet A. Gerrard, Andrew J. Pratt, James A.E. Kraunsoe
Rok vydání:	1996
Předmět:	chemistry.chemical_classification Aqueous solution Stereochemistry Lactol Organic Chemistry Biochemistry Aldehyde chemistry.chemical_compound Hydrolysis chemistry Heteronuclear molecule Drug Discovery Enol ether Methanol Hydrate
Zdroj:	Tetrahedron. 52:7127-7136
ISSN:	0040-4020
DOI:	10.1016/0040-4020(96)00330-4
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::5d6c4d749eef3f9843a165cfa4a208c0 https://doi.org/10.1016/0040-4020(96)00330-4 Zobrazit plný text záznamu Full Text from ScienceDirect