Assembly state of catalytic modules as chiral switches in asymmetric strecker amino acid synthesis

Nobuki Kato, Tsuyoshi Mita, Motomu Kanai, Bruno Therrien, Masaki Kawano, Kentaro Yamaguchi, Hiroshi Danjo, Yoshihisa Sei, Akihiro Sato, Sanae Furusho, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

110 Citations (Scopus)

Abstract

Self-assembled chiral polymetallic complexes often demonstrate novel properties as asymmetric catalysts. We report the three-dimensional structures of two such asymmetric catalysts (crystals A and B) for Strecker α,α-disubstituted amino acid synthesis. These complexes are constructed via assembly of the same chiral modules derived from d-glucose, but their assembly modes differ. The enantioselectivity in the Strecker reaction was dramatically switched, depending on which assembly mode was used: the catalyst generated in situ whose structure is represented by crystal B, or by crystal A. These findings provide insight into the functional importance of higher-order structures of an artificial catalyst.

Original languageEnglish
Pages (from-to)6768-6769
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number21
DOIs
Publication statusPublished - 2006 May 31
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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