SYNTHESIS AND STEREOCHEMISTRY OF BILIRUBIN ANALOGS LACKING CARBOXYLIC-ACIDS

Authors
BOIADJIEV SE PFEIFFER WP LIGHTNER DA
Citation
Se. Boiadjiev et al., SYNTHESIS AND STEREOCHEMISTRY OF BILIRUBIN ANALOGS LACKING CARBOXYLIC-ACIDS, Tetrahedron, 53(43), 1997, pp. 14547-14564
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
43
Year of publication
1997
Pages
14547 - 14564
Database
ISI
SICI code
0040-4020(1997)53:43<14547:SASOBA>2.0.ZU;2-W
Abstract
Bilirubin analogs with propionic acid groups replaced by ser-butyl (1) , 3-acetoxy-1-methylpropyl (2) or 3-acetamido-1-methylpropyl (3) were synthesized in enantiopure form and known absolute configuration. Alth ough there are no propionic acid groups to act in stabilizing folded, ridge-tile conformations, the (S) stereogenic centers induce the pigme nts to adopt a left-handed (M) helicity - as evidenced by exciton circ ular dichroism spectra. (C) 1997 Elsevier Science Ltd.