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Cyclodextrins tethered with oligolactides – green synthesis and structural assessment
Biodegradable oligolactide derivatives based on α-, β- and γ-cyclodextrins (CDs) were synthesized by a green procedure in which CDs play the role of both the initiator and the catalyst. The synthetic procedure in which CDs and L-lactide (L-LA) are reacting in bulk at relatively high temperature of 1...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5433207/ https://www.ncbi.nlm.nih.gov/pubmed/28546834 http://dx.doi.org/10.3762/bjoc.13.77 |
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author | Peptu, Cristian Balan-Porcarasu, Mihaela Šišková, Alena Škultéty, Ľudovít Mosnáček, Jaroslav |
author_facet | Peptu, Cristian Balan-Porcarasu, Mihaela Šišková, Alena Škultéty, Ľudovít Mosnáček, Jaroslav |
author_sort | Peptu, Cristian |
collection | PubMed |
description | Biodegradable oligolactide derivatives based on α-, β- and γ-cyclodextrins (CDs) were synthesized by a green procedure in which CDs play the role of both the initiator and the catalyst. The synthetic procedure in which CDs and L-lactide (L-LA) are reacting in bulk at relatively high temperature of 110 °C was investigated considering the structural composition of the products. The obtained products were thoroughly characterized via mass spectrometry methods with soft ionization like matrix-assisted laser desorption ionization (MALDI) and electrospray ionization (ESI). Liquid chromatography (LC) separation with evaporative light scattering detection (ELSD) and NMR analysis were employed in order to elucidate the structural profiles of the obtained mixtures. The results clearly demonstrate that the cyclodextrins were tethered with more than one short oligolactate chain per CD molecule, predominantly at the methylene group, through ring opening of L-LA initiated by primary OH groups. |
format | Online Article Text |
id | pubmed-5433207 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-54332072017-05-25 Cyclodextrins tethered with oligolactides – green synthesis and structural assessment Peptu, Cristian Balan-Porcarasu, Mihaela Šišková, Alena Škultéty, Ľudovít Mosnáček, Jaroslav Beilstein J Org Chem Full Research Paper Biodegradable oligolactide derivatives based on α-, β- and γ-cyclodextrins (CDs) were synthesized by a green procedure in which CDs play the role of both the initiator and the catalyst. The synthetic procedure in which CDs and L-lactide (L-LA) are reacting in bulk at relatively high temperature of 110 °C was investigated considering the structural composition of the products. The obtained products were thoroughly characterized via mass spectrometry methods with soft ionization like matrix-assisted laser desorption ionization (MALDI) and electrospray ionization (ESI). Liquid chromatography (LC) separation with evaporative light scattering detection (ELSD) and NMR analysis were employed in order to elucidate the structural profiles of the obtained mixtures. The results clearly demonstrate that the cyclodextrins were tethered with more than one short oligolactate chain per CD molecule, predominantly at the methylene group, through ring opening of L-LA initiated by primary OH groups. Beilstein-Institut 2017-04-26 /pmc/articles/PMC5433207/ /pubmed/28546834 http://dx.doi.org/10.3762/bjoc.13.77 Text en Copyright © 2017, Peptu et al. https://creativecommons.org/licenses/by/4.0https://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/4.0), 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 Peptu, Cristian Balan-Porcarasu, Mihaela Šišková, Alena Škultéty, Ľudovít Mosnáček, Jaroslav Cyclodextrins tethered with oligolactides – green synthesis and structural assessment |
title | Cyclodextrins tethered with oligolactides – green synthesis and structural assessment |
title_full | Cyclodextrins tethered with oligolactides – green synthesis and structural assessment |
title_fullStr | Cyclodextrins tethered with oligolactides – green synthesis and structural assessment |
title_full_unstemmed | Cyclodextrins tethered with oligolactides – green synthesis and structural assessment |
title_short | Cyclodextrins tethered with oligolactides – green synthesis and structural assessment |
title_sort | cyclodextrins tethered with oligolactides – green synthesis and structural assessment |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5433207/ https://www.ncbi.nlm.nih.gov/pubmed/28546834 http://dx.doi.org/10.3762/bjoc.13.77 |
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