Facile syntheses of l-β-haloalanine derivatives from l-cysteine or l-cystine.

Autor:	Feiyan Tao, Yinggang Luo, Qingchun Huang, Yan Liu, Bogang Li, Guolin Zhang
Předmět:	AMINO acid synthesis ALANINE GLYCOPEPTIDES FUNCTIONAL groups HALOGENATION DESULFURIZATION SUCCINIMIDES
Zdroj:	Amino Acids; Oct2009, Vol. 37 Issue 4, p603-607, 5p
Abstrakt:	Abstract   l-β-Haloalanines are physiologically active unnatural amino acids and they are useful intermediates for the synthesis of natural and unnatural amino acids, S-linked glycopeptides, and lanthionines. In general l-β-haloalanines were prepared predominantly from l-serine via functional group transformation. Here we reported an alternative approach for the preparation of l-β-haloalanines via halogenation of protected l-cysteine esters which was obtained from l-cysteine or l-cystine, respectively. The mercapto group of protected l-cysteine esters was efficiently transformed to halo groups by triphenylphosphine/N-halosuccinimides. It has been proved to be a versatile desulfurization strategy via this functional group transformation. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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