Synthesis of 11-cis-locked bicyclo[5.1.0]octanyl retinal and an enantioselective binding to bovine opsin |
| |
Authors: | Fujimoto Yukari Xie Rongyuan Tully Sarah E Berova Nina Nakanishi Koji |
| |
Affiliation: | Department of Chemistry, Columbia University, New York, New York 10027, USA. |
| |
Abstract: | Both enantiomers of 13-(E) and 13-(Z) isomers of 11-cis-locked bicyclo[5.1.0]octanyl retinal were prepared by an improved synthesis and incubated with bovine opsin. The synthesis also establishes the absolute configuration of the enantiomers. Only one of the enantiomers binds to opsin, thus showing the steric restrictions regarding the middle polyene moiety of the retinoid molecule; this is in sharp contrast to the known leniency of the ring moiety binding site of retinoids. However, although one enantiomer is incorporated into the pigment, the circular dichroic spectrum of the pigment incorporating the bound enantiomer yields only a very weak Cotton effect, showing that, once incorporated, the bicyclo[5.1.0]octanyl chromophore is flattened by the opsin binding site. The titled retinoid was synthesized for study of the absolute conformation of the retinal pigment in rhodopsin. |
| |
Keywords: | cyclopropyl retinoid rhodopsin circular dichroic spectroscopy (CD) chiral separation chiral discrimination exciton coupled CD |
本文献已被 PubMed 等数据库收录! |
|