SYNTHESIS AND CONFORMATION OF A BILIRUBIN ANALOG WITH PROPIONIC-ACID SIDE-CHAINS EXTENDED TO UNDECANOIC ACID

被引：7

作者：

CHIEFARI, J ^{[1
]}

PERSON, RV ^{[1
]}

LIGHTNER, DA ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1992年 / 48卷 / 29期

关键词：

D O I：

10.1016/S0040-4020(01)89846-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A lipophilic analog of bilirubin with propionic acid groups replaced by undecanoic acid groups (1), was synthesized from 11-bromo-undecanoic acid. UV-visible and NMR spectroscopic analyses suggest reduced intramolecular H-bonding and a preference for a helical conformation. Molecular dynamics computations predict a global energy minimum for a helical porphyrin-like conformation with unusual distorted structures when H-bonding is invoked. Circular dichroism of the pigment complex with human serum albumin gives a bilirubin-like bisignate Cotton effect: DELTA-epsilon(449)max = + 33, DELTA-epsilon(396)max = -47.

引用

页码：5969 / 5984

页数：16

共 35 条

[1] BILE PIGMENT STRUCTURES .2. CRYSTAL-STRUCTURE OF MESOBILIRUBIN-IX-ALPHA-BIS(CHLOROFORM) [J].