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Hydrophobic Interaction of Chromophoresin Visual Pigment Formation

发色团视觉色素形成的疏水相互作用

基本信息

批准号：
04640523
负责人：
TSUJIMOTO Kazuo
金额：
$ 1.34万
依托单位：
JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY, HOKURIKU (1993)The University of Electro-Communications (1992)
依托单位国家：
日本
项目类别：
Grant-in-Aid for General Scientific Research (C)
财政年份：
1992
资助国家：
日本
起止时间：
1992 至 1993
项目状态：
已结题

项目摘要

1. Hydrophobic Interaction around beta-IononeRing of Chromophores5,6-Dihydro-, 7,8-dihydro-, alpha-, and 3,4-dehydroretinals were synthesized Pigment formation of the retinal analogs with aporetinochrome resulted in apparent completion with loose hydrophobic interaction around the beta-ionone ring.2. Opsin Shifts of Retinal Analogs without beta-Ionone RingThe opsin shift of the structurely linear analog, 3,7-dodecapentaenal showed 1400 cm^<-1> smaller value of the neative one, 2400 cm^<-1>.3. The Conformation of Retinochrome Chromophore in 6S-BondWith 6S-cis locked retinal analog, the pigment were formed as in native retinochrome formation, while 6S-trans locked analog gave no pigment.4. Regiospecific Photoisomerization of Retinal AnalogsPhotoisomerization of 3,7-DDP with aporetinochrome regiospecifically gave 11-cis typed isomer, whereas 3,7-DDT did not show the high selectivity, 43%.5. CD Spectra of 6S-Cis Locked Retinal AnalogsThe retinochrome analogs with 8,18-methano- and ethanoretinal gave intense and negative beta-band compared with positive alpha-band.6.11-Methylretinal Analogs11-Methyl-, 13-demethyl-11-methyl-, and 9, 13-didemethyl- 11-methylretinals were synthesized. The conformation of all-trans 11-methylretinal were determined to be 10,12-di-S-cis. Photoisomerization of these analogs with aporetinochrome furnished corresponding 11-cis isomers in more than 90% regioselectivity.

1.合成了5，6-二氢-，7，8-二氢-，α-和3，4-脱氢视黄酸类化合物。用脱辅基视黄色素合成的视黄酸类似物的色素形成在β-紫罗酮环周围产生了松散的疏水作用。不含β-紫罗兰酮环的视网膜类似物的视蛋白位移结构线性类似物3，7-十二碳五烯醛的视蛋白位移值比<-1>阴性类似物2400 cm^小1400 cm^<-1>。视网膜色素发色团在6S-键上的构象6S-顺式锁定的视网膜色素类似物能像天然视网膜色素一样形成色素，而6S-反式锁定的类似物不产生色素.视网膜类似物的区域特异性光异构化3，7-DDP与脱维A色素的光异构化区域特异性地产生11-顺式异构体，而3，7-DDT没有显示出高的选择性，为43%。6S-顺式锁定视网膜类似物的圆二色性（CD）光谱与8，18-亚甲基-和乙醇-视网膜醛反应的维甲酸色素类似物产生较强的负β带，而α带为正。全反式11-甲基视黄醛的构象为10，12-di-S-cis。这些类似物的光异构化与aporetinochrome提供相应的11-顺式异构体在90%以上的区域选择性。