aS,7S‐absolute configuration of natural (−)‐colchicine and allocongeners

FEBS Letters

George, Clifford¹  Brossi, Arnold³  Toome, Voldemar⁴  Boyé, Olivier³  Muzaffar, Anjum³  Yeh, Herman J.C.²  Wegrzynski, Bogda⁴ 

[1] Laboratory for the Structure of Matter, Naval Research Laboratory, Washington, DC 20375-9000, USA;Laboratory of Analytical Chemistry, NIDDK, National Institutes of Health, Bethesda, MD 20892 USA;Natural Products Section, Laboratory of Structural Biology, NIDDK, National Institutes of Health, Bethesda, MD 20892 USA;Research Division, Hoffmann-La Roche Inc., Nutley, NJ 07110 USA

关键词: Colchicine;    Allocolchicine;    Tubulin binding;   

DOI  :  10.1016/0014-5793(90)80139-A

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

The aS,7S-absolute configuration of (−)-colchicine (1) and (−)-N-acetylcolchinol methyl ether (3, NCME) suggested on the basis of ¹H NMR data and negative Cotton effects at about 260 nm (EtOH) is firmly established by an X-ray analysis of urea 5, a compound derived from 3. Binding of these compounds to tubulin requires an aS-configuration of the biaryl system.

【 授权许可】

Unknown