Chiral recognition and supramolecular photoreaction of 1,1'-binaphthol with bovine and human serum albumins

摘要

In their pioneering study in 1991, Levi-Minzi and Zandomeneghi discovered that photoirradiation of racemic 1,1'-binaphthol (rac-1) in the presence of bovine serum albumin (BSA) in distilled water gave (R)-1 in 99 % enantiomeric excess (ee) after 77 % of the starting material had been consumed. No similar attempt was made with human serum albumin (HSA). In this study of the effects of phosphate buffer solution on the ground-state affinity and excited-state photobehavior of 1 with serum albumin we found that both BSA and HSA preferentially bind the (S) enantiomer of 1 and that photoreaction of rac-1 mediated by BSA and HSA affords (R)-1 in 98 % ee with 99 % conversion and in 46 % ee with 65 % conversion, respectively.