Chiral recognition and supramolecular photoreaction of 1,1′-binaphthol with bovine and human serum albumins
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.
KeywordsChiral photochemistry Serum albumin Binaphthol Supramolecular photochirogenesis
This work was supported by a Grant-in-Aid for Scientific Research (A) (no. 21245011; YI) and (B) (no. 23350018; TM) from the Japan Society for the Promotion of Science, and a Grant for Basic Science Research from The Sumitomo Foundation (no. 080435; MN), which are gratefully acknowledged.
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