Synthesis and reactions of Biginelli compounds, part 19 - X-ray structure,conformational analysis, enantioseparation, and determination of absolute configuration of the mitotic kinesin Eg5 inhibitor monastrol

Authors
Kappe, CO Shishkin, OV Uray, G Verdino, P
Citation
Co. Kappe et al., Synthesis and reactions of Biginelli compounds, part 19 - X-ray structure,conformational analysis, enantioseparation, and determination of absolute configuration of the mitotic kinesin Eg5 inhibitor monastrol, TETRAHEDRON, 56(13), 2000, pp. 1859-1862
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
13
Year of publication
2000
Pages
1859 - 1862
Database
ISI
SICI code
0040-4020(20000324)56:13<1859:SAROBC>2.0.ZU;2-5
Abstract
The conformational features of the mitotic kinesin Eg5 inhibitor monastrol were investigated by computational (AM1, HF/3-21G*), X-ray diffraction, and NMR studies showing that monastrol is a conformationally highly flexible m olecule. Racemic monastrol was resolved by direct enantioselective HPLC and thr absolute configuration of the first eluting (S)-(+) enantiomer was est ablished by CD spectroscopy. (C) 2000 Elsevier Science Ltd. All rights rese rved.