Experimental and theoretical analysis of the steric tolerance of the binding site of bacterioopsin with the use of side-chain methyl-shifted retinal analogs

…, B Iglesias, J Rodriguez, R Alvarez…

Index: De Lera, Angel R.; Iglesias, Beatriz; Rodriguez, Jesus; Alvarez, Rosana; Lopez, Susana; Villanueva, Xavier; Padros, Esteve Journal of the American Chemical Society, 1995 , vol. 117, # 31 p. 8220 - 8231

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Citation Number: 53

Abstract

Abstract: Four positional isomers of trans-retinal (1) differing in the location of the side-chain methyl groups have been prepared by a combination of Wittig and highly stereocontrolled Suzuki coupling reactions. The incubation of 9-demethyl-10-methylretinal (5) with bacterioopsin yielded an artificial pigment with an opsin sh@ of 4630 cm-'. The other three analogs, namely 13-demethyl-14-methylretinal (3), 13-demethyl-12-methylretinal (4), and ...