Mammalian serum albumins as a chiral mediator library for bio-supramolecular photochirogenesis: Optimizing enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate

Masaki Nishijima, Masato Goto, Mayu Fujikawa, Cheng Yang, Tadashi Mori, Takehiko Wada, Yoshihisa Inoue

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

A simple strategy for choosing optimal bio-supramolecular mediators from the mammalian serum albumin library is proposed for bimolecular photochirogenic reactions. Thus, the enantiodifferentiating photocyclodimerization of 2-anthracencecarboxylate (AC) was optimized in chemical and optical yields, when mediated by porcine and canine serum albumins, both of which bound two AC molecules in the first productive site to give the (P)-enantiomer of syn-head-to-tail-cyclodimer in 69% yield and 89% enantiomeric excess (ee) for the former but the (M)-enantiomer in 77% yield and 97% ee for the latter.

Original languageEnglish
Pages (from-to)14082-14085
Number of pages4
JournalChemical Communications
Volume50
Issue number91
DOIs
Publication statusPublished - 2014 Oct 21

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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