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Optimized methods for preparation of 6(I)-(ω-sulfanyl-alkylene-sulfanyl)-β-cyclodextrin derivatives
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 wer...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4778511/ https://www.ncbi.nlm.nih.gov/pubmed/26977195 http://dx.doi.org/10.3762/bjoc.12.38 |
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author | Bednářová, Eva Hybelbauerová, Simona Jindřich, Jindřich |
author_facet | Bednářová, Eva Hybelbauerová, Simona Jindřich, Jindřich |
author_sort | Bednářová, Eva |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-4778511 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-47785112016-03-14 Optimized methods for preparation of 6(I)-(ω-sulfanyl-alkylene-sulfanyl)-β-cyclodextrin derivatives Bednářová, Eva Hybelbauerová, Simona Jindřich, Jindřich Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2016-02-24 /pmc/articles/PMC4778511/ /pubmed/26977195 http://dx.doi.org/10.3762/bjoc.12.38 Text en Copyright © 2016, Bednářová et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Full Research Paper Bednářová, Eva Hybelbauerová, Simona Jindřich, Jindřich Optimized methods for preparation of 6(I)-(ω-sulfanyl-alkylene-sulfanyl)-β-cyclodextrin derivatives |
title | Optimized methods for preparation of 6(I)-(ω-sulfanyl-alkylene-sulfanyl)-β-cyclodextrin derivatives |
title_full | Optimized methods for preparation of 6(I)-(ω-sulfanyl-alkylene-sulfanyl)-β-cyclodextrin derivatives |
title_fullStr | Optimized methods for preparation of 6(I)-(ω-sulfanyl-alkylene-sulfanyl)-β-cyclodextrin derivatives |
title_full_unstemmed | Optimized methods for preparation of 6(I)-(ω-sulfanyl-alkylene-sulfanyl)-β-cyclodextrin derivatives |
title_short | Optimized methods for preparation of 6(I)-(ω-sulfanyl-alkylene-sulfanyl)-β-cyclodextrin derivatives |
title_sort | optimized methods for preparation of 6(i)-(ω-sulfanyl-alkylene-sulfanyl)-β-cyclodextrin derivatives |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4778511/ https://www.ncbi.nlm.nih.gov/pubmed/26977195 http://dx.doi.org/10.3762/bjoc.12.38 |
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