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

Masaki Nishijima, Jae Won Chang, Cheng Yang, Gaku Fukuhara, Tadashi Mori, Yoshihisa Inoue

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)371-383
Number of pages13
JournalResearch on Chemical Intermediates
Volume39
Issue number1
DOIs
Publication statusPublished - 2013 Jan 1
Externally publishedYes

Keywords

  • Binaphthol
  • Chiral photochemistry
  • Serum albumin
  • Supramolecular photochirogenesis

ASJC Scopus subject areas

  • Chemistry(all)

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