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

doi:10.1021/ol006235x

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 journal › Article › peer-review

38 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 (K_D/K_L) arising from the guest's depth of penetration into the host's cavity.

Original language	English
Pages (from-to)	3257-3260
Number of pages	4
Journal	Organic Letters
Volume	2
Issue number	21
DOIs	https://doi.org/10.1021/ol006235x
Publication status	Published - 2000 Oct 19
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

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AU - Hembury, Guy

AU - Rekharsky, Mikhail

AU - Nakamura, Asao

AU - Inoue, Yoshihisa

PY - 2000/10/19

Y1 - 2000/10/19

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AB - (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.

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

Abstract

ASJC Scopus subject areas

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