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Optimized methods for preparation of 6(I)-(ω-sulfanyl-alkylene-sulfanyl)-β-cyclodextrin derivatives.

Research paper by Eva E Bednářová, Simona S Hybelbauerová, Jindřich J Jindřich

Indexed on: 16 Mar '16Published on: 16 Mar '16Published in: Beilstein journal of organic chemistry



Abstract

A general high-yielding method for the preparation of monosubstituted β-cyclodextrin derivatives which have attached a thiol group in position 6 is described. The thiol group is attached through linkers of different lengths and repeating units (ethylene glycol or methylene). The target compounds were characterized by IR, MS and NMR spectra. A simple method for their complete conversion to the corresponding disulfides as well as a method for the reduction of the disulfides back to the thiols is presented. Both, thiols and disulfides are derivatives usable for well-defined covalent attachment of cyclodextrin to gold or polydopamine-coated solid surfaces.