Direct correlation between complex conformation and chiral discrimination upon inclusion of amino acid derivatives by β- and γ-cyclodextrins

Guy Hembury, Mikhail Rekharsky, Asao Nakamura, Yoshihisa Inoue

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

(matrix presented) A correlation between the conformation and chiral recognition characteristics of a series of modified amino acid complexes with β- and γ-cyclodextrins has been determined, using titration microcalorimetry and 1H NMR techniques. The enantiomeric discrimination (D or L) is found to be dependent on the adoption of one of two distinct conformations. With the magnitude of the chiral discrimination (KD/KL) arising from the guest's depth of penetration into the host's cavity.

Original languageEnglish
Pages (from-to)3257-3260
Number of pages4
JournalOrganic Letters
Volume2
Issue number21
DOIs
Publication statusPublished - 2000 Oct 19
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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