Issue 10, 2015

A γ-cyclodextrin duplex connected with two disulfide bonds: synthesis, structure and inclusion complexes

Abstract

Per(2,3,6-tri-O-benzyl)-γ-cyclodextrin was debenzylated by DIBAL-H to produce a mixture of C6I,C6IV and C6I,C6V isomeric diols, which were separated and isolated. The C2-symmetrical C6I,C6V diol was transformed into dithiol and dimerized to produce a γ-cyclodextrin duplex structure. A crystal structure revealed tubular cavity whose peripheries are slightly elliptically distorted. The solvent accessible volume of the cavity of the γ-CD duplex is about 740 Å3. Due to this large inner space the duplex forms very stable inclusion complexes with steroids; bile acids examined in this study show binding affinities to the γ-cyclodextrin duplex in the range of 5.3 × 107 M−1–1.9 × 108 M−1.

Graphical abstract: A γ-cyclodextrin duplex connected with two disulfide bonds: synthesis, structure and inclusion complexes

Supplementary files

Article information

Article type
Paper
Submitted
24 nov 2014
Accepted
11 jan 2015
First published
12 jan 2015
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2015,13, 2980-2985

Author version available

A γ-cyclodextrin duplex connected with two disulfide bonds: synthesis, structure and inclusion complexes

S. Volkov, L. Kumprecht, M. Buděšínský, M. Lepšík, M. Dušek and T. Kraus, Org. Biomol. Chem., 2015, 13, 2980 DOI: 10.1039/C4OB02464H

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