Synthesis and conformational analysis of a chiral fluorinated bilirubin analog lacking carboxyl groups

Authors
Boiadjiev, SE Lightner, DA
Citation
Se. Boiadjiev et Da. Lightner, Synthesis and conformational analysis of a chiral fluorinated bilirubin analog lacking carboxyl groups, J HETERO CH, 36(4), 1999, pp. 969-977
Citations number
36
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022152X → ACNP
Volume
36
Issue
4
Year of publication
1999
Pages
969 - 977
Database
ISI
SICI code
0022-152X(199907/08)36:4<969:SACAOA>2.0.ZU;2-P
Abstract
An optically active analog 1 of etiobilirubin-IV gamma with a single fluori ne on each of the C(8) and C(12) alkyl groups has been synthesized in order to examine its potential for hydrogen bonding with fluorine. Circular dich roism spectroscopy reveals an unusually strong influence of 2,2,2-trifluoro ethanol solvent on diastereo-selection of the M-helical conformation of (8( 1)S, 12(1)S)-1.