VISUAL PIGMENTS AND BACTERIORHODOPSINS FORMED FROM AROMATIC RETINAL ANALOGS

Abstract

Abstract— Rhodopsin (Rh) and bacteriorhodopsin (bR) analogs have been prepared from retinals containing various aromatic and heterocyclic nuclei. In the case of Rh, aromatic methyl substituents facilitate the regeneration and stabilize the pigments formed; in bR, however, methyl substituents seem to have little influence. Rhodopsins derived from unsubstituted aromatic retinals show fine structure in the relatively stable “pre‐pigment” intermediate and their maxima are red‐shifted compared to pigments derived from methylated aromatic retinals. This implies that in these aromatic rhodopsins the ring moiety adopts a more planar conformation when unsubstituted. In bR derivatives also the aromatic ring adopts a close‐to‐planar conformation when unsubstituted, but comparison with indene‐derived bR suggests that even the unsubstituted phenyl ring may not be coplanar with the side‐chain.