SYNTHESIS OF (+)-(4S)- AND (-)-(4R)-11Z-4-HYDROXYRETINALS AND DETERMINATION OF THE ABSOLUTE STEREOCHEMISTRY OF A VISUAL PIGMENT CHROMOPHORE IN THE BIOLUMINESCENT SQUID, WATASENIA SCINTILLANS

被引：12

作者：

KATSUTA, Y

YOSHIHARA, K

NAKANISHI, K

ITO, M

机构：

[1] KOBE WOMENS COLL PHARM,KOBE 658,JAPAN

[2] SUNTORY INST BIOORGAN RES,OSAKA 618,JAPAN

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

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 06期

关键词：

(4S)- AND (4R)-11Z-4-HYDROXYRETINAL; VISUAL PIGMENT; ABSOLUTE CONFIGURATION; CIRCULAR DICHROISM (CD); EXCITON CHIRALITY METHOD;

D O I：

10.1016/S0040-4039(00)75995-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of (+)-(4S)- and (-)-(4R)-11Z-4-hydroxyretinals (4-OH-RALs) la and Ib was accomplished from (4S)- and (4R)-4-hydroxy-beta-ionones, respectively, to determine the absolute configuration of a visual pigment chromophore in Watasenia scintillans. The CD spectra of the native chromophore and its anti-oxime agreed with those of synthetic (4R)-compounds. The CD exciton chirality method as applied to the p-dimethylaminocinnamate of (4R)-4-OH-RAL also establishes the absolute configuration of the native chromophore as

引用

页码：905 / 908

页数：4

共 8 条

[1] CD EXCITON CHIRALITY METHOD - NEW RED-SHIFTED CHROMOPHORES FOR HYDROXYL-GROUPS [J].