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

0443750 - ÚOCHB 2016 RIV GB eng J - Článek v odborném periodiku
Volkov, Sergey - Kumprecht, Lukáš - Buděšínský, Miloš - Lepšík, Martin - Dušek, Michal - Kraus, Tomáš
A gamma-cyclodextrin duplex connected with two disulfide bonds: synthesis, structure and inclusion complexes.
Organic & Biomolecular Chemistry. Roč. 13, č. 10 (2015), s. 2980-2985. ISSN 1477-0520. E-ISSN 1477-0539
Grant CEP: GA MŠMT LD12019; GA ČR(CZ) GA14-03276S
Institucionální podpora: RVO:61388963 ; RVO:68378271
Klíčová slova: bridged beta-cyclodextrin * strong binding * molecular recognition
Kód oboru RIV: CC - Organická chemie; BM - Fyzika pevných látek a magnetismus (FZU-D)
Impakt faktor: 3.559, rok: 2015
http://pubs.rsc.org/en/content/articlepdf/2015/ob/c4ob02464h

Per(2,3,6-tri-O-benzyl)-gamma-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 C-2-symmetrical C6(I), C6(V) diol was transformed into dithiol and dimerized to produce a gamma-cyclodextrin duplex structure. A crystal structure revealed tubular cavity whose peripheries are slightly elliptically distorted. The solvent accessible volume of the cavity of the gamma-CD duplex is about 740 angstrom(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 gamma-cyclodextrin duplex in the range of 5.3 x 10(7) M-1-1.9 x 10(8) M-1.
Trvalý link: http://hdl.handle.net/11104/0246449