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
Publication statusPublished - 2000 Oct 19
Externally publishedYes

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Cyclodextrins
amino acids
discrimination
Conformations
inclusions
Amino Acids
Titration
titration
penetration
Nuclear magnetic resonance
nuclear magnetic resonance
cavities
matrices

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Direct correlation between complex conformation and chiral discrimination upon inclusion of amino acid derivatives by β- and γ-cyclodextrins. / Hembury, Guy; Rekharsky, Mikhail; Nakamura, Asao; Inoue, Yoshihisa.

In: Organic Letters, Vol. 2, No. 21, 19.10.2000, p. 3257-3260.

Research output: Contribution to journalArticle

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