Facile syntheses of L-beta-haloalanine derivatives from L-cysteine or L-cystine.
L-beta-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-beta-haloalanines were prepared predominantly from L-serine via functional group transformation. Here we reported an alternative approach for the preparation of L-beta-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.
Center for Natural Products Research, Chengdu Institute of Biology, Chinese Academy of Sciences, 610041, Chengdu, People's Republic of China.
Feiyan
F
Tao
Yinggang
Y
Luo
Qingchun
Q
Huang
Yan
Y
Liu
Bogang
B
Li
Guolin
G
Zhang
D003545:Cysteine / Q000737:chemistry*; D003553:Cystine / Q000737:chemistry*; D054879:Halogenation; D006219:Halogens / Q000737:chemistry; D015091:beta-Alanine / Q000031:analogs & derivatives*
D006219:Halogens; D015091:beta-Alanine; D003553:Cystine; D003545:Cysteine