HELICALLY FIXED CHIRAL BILIRUBINS AND BILIVERDINS - A NEW INSIGHT INTO THE CONFORMATIONAL, ASSOCIATIVE AND DYNAMIC FEATURES OF LINEAR TETRAPYRROLS

被引：25

作者：

KROIS, D ^{[1
]}

LEHNER, H ^{[1
]}

机构：

[1] UNIV VIENNA, INST ORGAN CHEM, WAHRINGERSTR 38, A-1090 VIENNA, AUSTRIA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1993年 / 07期

关键词：

D O I：

10.1039/p29930001351

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 2,18-bridged biliverdins 1, 2 and 5 and bilirubins 3, 4 and 6 each forced into a helical conformation have been prepared and investigated by UV-VIS spectroscopy, H-1 NMR spectroscopy techniques and vapour pressure osmometry. Barriers to interconversion of the tetrapyrrole moieties of M and P chirality were accomplished by kinetic measurements of partially resolved materials using CD spectroscopy. These results were compared with those obtained for non-bridged analogues reported here and in the literature. Based on the above, the structural and environmental factors controlling the dynamic, associative and conformational behaviour of biliverdins and bilirubins have been established. In this connection the complete conformational and associative pattern of bilirubin-IXalpha-dimethyl ester (10) is presented.

引用

页码：1351 / 1360

页数：10

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