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Bednářová E, Hybelbauerová S, Jindřich J. Optimized methods for preparation of 6(I)-(ω-sulfanyl-alkylene-sulfanyl)-β-cyclodextrin derivatives. Beilstein J Org Chem. 2016;12:349-52doi: 10.3762/bjoc.12.38.
Bednářová, E., Hybelbauerová, S., & Jindřich, J. (2016). Optimized methods for preparation of 6(I)-(ω-sulfanyl-alkylene-sulfanyl)-β-cyclodextrin derivatives. Beilstein journal of organic chemistry, 12349-52. https://doi.org/10.3762/bjoc.12.38
Bednářová, Eva, et al. "Optimized methods for preparation of 6(I)-(ω-sulfanyl-alkylene-sulfanyl)-β-cyclodextrin derivatives." Beilstein journal of organic chemistry vol. 12 (2016): 349-52. doi: https://doi.org/10.3762/bjoc.12.38
Bednářová E, Hybelbauerová S, Jindřich J. Optimized methods for preparation of 6(I)-(ω-sulfanyl-alkylene-sulfanyl)-β-cyclodextrin derivatives. Beilstein J Org Chem. 2016 Feb 24;12:349-52. doi: 10.3762/bjoc.12.38. eCollection 2016. PMID: 26977195; PMCID: PMC4778511.
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Beilstein J Org Chem. 2016 Feb 24;12:349-52. doi: 10.3762/bjoc.12.38. eCollection 2016.

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

Beilstein journal of organic chemistry

Eva Bednářová, Simona Hybelbauerová, Jindřich Jindřich

Affiliations

  1. Department of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43, Prague 2, Czech Republic.
  2. Department of Teaching and Didactics of Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43, Prague 2, Czech Republic.

PMID: 26977195 PMCID: PMC4778511 DOI: 10.3762/bjoc.12.38

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.

Keywords: cyclodextrins; disulfides; monosubstituted derivatives; thiols

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