Stereogenic competition in bilirubin conformational enantiomerism

被引：13

作者：

Boiadjiev, SE ^{[1
]}

Lightner, DA ^{[1
]}

机构：

[1] UNIV NEVADA,DEPT CHEM,RENO,NV 89557

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 13期

关键词：

D O I：

10.1016/S0957-4166(97)00206-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Optically active bilirubin analogs (1 and 2) with a stereogenic center in each propionic acid side chain were synthesized and examined by CD and NMR spectroscopy. Introduction of an alpha-methyl and a beta-methyl forces the pigment to adopt either a left-handed (M) or right-handed (P) helicity with a folded, ridge-tile conformation. As evidenced by exciton-type circular dichroism spectra, the (alpha S, alpha'S-3), (beta S, beta'S-5), (alpha S, beta'S-1) stereoisomers strongly prefer the M-helicity ridge-tile conformation, but the (alpha R, beta'S) stereoisomer (2) prefers the P-helicity. (C) 1997 Elsevier Science Ltd.

引用

页码：2115 / 2129

页数：15

共 32 条

[1]

[Anonymous], 1989, NUCL OVERHAUSER EFFE, DOI DOI 10.1002/MRC.1260280819

[2] CONFORMATION OF BILIRUBIN AND BILIVERDIN IN THEIR COMPLEXES WITH SERUM-ALBUMIN [J].