Abstract
Per-O-methyl-6I,6IV-disulfanyl-6I,6IV-dideoxy-α-cyclodextrin undergoes air oxidation at pH 9 to exclusively form a monomeric species having an intramolecular disulfide linkage capping the C6I and C6IV positions. In contrast, its non-methylated analogue, 6I,6IV-disulfanyl-6I,6IV-dideoxy-α-cyclodextrin, gives a mixture of monomeric and dimeric species under the same conditions. Molecular models show that in both cases of the monomeric species, the disulfide bonds effectively close the primary rims of the cyclodextrin cavities. The disulfide bonds of the capped cyclodextrins could be cleaved by reduction with dithiothreitol. Thus, the macrocyclic system can interchange the open-ended and cup-like forms by the application of external stimuli.
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