SYNTHESIS OF RETINALS WITH 8-MEMBERED AND 9-MEMBERED RINGS IN THE SIDE-CHAIN - MODELS FOR RHODOPSIN PHOTOBLEACHING INTERMEDIATES

被引：11

作者：

CALDWELL, CG ^{[1
]}

DERGUINI, F ^{[1
]}

BIGGE, CF ^{[1
]}

CHEN, AH ^{[1
]}

HU, SH ^{[1
]}

WANG, J ^{[1
]}

SASTRY, L ^{[1
]}

NAKANISHI, K ^{[1
]}

机构：

[1] COLUMBIA UNIV,DEPT CHEM,NEW YORK,NY 10027

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 13期

关键词：

D O I：

10.1021/jo00065a014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The triggering process of rhodopsin activation leading to visual transduction has remained a key problem in the chemistry of vision. In order to provide probes to explore this process, retinal analogs ret8 3 and ret9 4, with the 11-ene cis-locked by 8- and 9-membered rings, have been synthesized. These could lead to pigment analogs which might accomodate a transoid chromophore upon irradiation, thus providing unique models for rhodopsin activation studies. Enzyme assays and flash photolysis of rhodopsin analogs incorporating ret8 and other retinal analogs showed that the triggering process requires complete 11-cis to trans isomerization involving the entire polyene moiety. The syntheses of ret8 3 and ret9 4 double bond isomers are described.

引用

页码：3533 / 3537

页数：5

共 28 条

[21] SYNTHESIS OF PROGESTERONE FROM DEHYDROEPIANDROSTERONE [J].