title: 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 C6(I),C6(IV) and C6(I),C6(V) isomeric diols, which were separated and isolated. The C2-symmetrical C6(I),C6(V) 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 Å(3). 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 × 10(7) M(-1)-1.9 × 10(8) M(-1).
authors.affiliation: Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic. kraus@uochb.cas.cz.
authors.forename: Sergey
authors.initials: S
authors.lastname: Volkov
authors.forename: Lukáš
authors.initials: L
authors.lastname: Kumprecht
authors.forename: Miloš
authors.initials: M
authors.lastname: Buděšínský
authors.forename: Martin
authors.initials: M
authors.lastname: Lepšík
authors.forename: Michal
authors.initials: M
authors.lastname: Dušek
authors.forename: Tomáš
authors.initials: T
authors.lastname: Kraus
mesh_terms: D002151:Calorimetry; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D018360:Crystallography, X-Ray; D019281:Dimerization; D004220:Disulfides / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D000068877:Imatinib Mesylate / Q000737:chemistry; D007700:Kinetics; D008095:Lithocholic Acid / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010100:Oxygen / Q000737:chemistry; D011485:Protein Binding; D012997:Solvents / Q000737:chemistry; D013256:Steroids / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013816:Thermodynamics; D047408:gamma-Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D004220:Disulfides; D012997:Solvents; D013256:Steroids; D013438:Sulfhydryl Compounds; D047408:gamma-Cyclodextrins; D008095:Lithocholic Acid; D000068877:Imatinib Mesylate; C023792:gamma-cyclodextrin; D010100:Oxygen