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Alpha-cyclodextrins reversibly capped with disulfide bonds
- 1.0350020 - ÚOCHB 2011 RIV GB eng J - Journal Article
Kumprecht, Lukáš - Buděšínský, Miloš - Bouř, Petr - Kraus, Tomáš
Alpha-cyclodextrins reversibly capped with disulfide bonds.
New Journal of Chemistry. Roč. 34, č. 10 (2010), s. 2254-2260. ISSN 1144-0546. E-ISSN 1369-9261
R&D Projects: GA AV ČR IAA400550810
Institutional research plan: CEZ:AV0Z40550506
Keywords : cyclodextrins * disulfide bond * dynamic covalent bond
Subject RIV: CC - Organic Chemistry
Impact factor: 2.631, year: 2010
Per-O-methyl-6I, 6IV-disulfanyl-6I, 6IV-dideoxy-alpha-cyclodextrin undergoes air-oxidation at pH 9 to exclusively form monomeric species having an intramolecular disulfide linkage capping the C6I and C6IV positions. Molecular models show that the disulfide bridge effectively closes the primary rim of the the cyclodextrin cavity and can be cleaved by reduction with dithiothreitol. Thus, the macrocyclic system can interchange the open-ended and cup-like forms by application of external stimuli.
Permanent Link: http://hdl.handle.net/11104/0190124
Number of the records: 1