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Synthesis of Randomly Substituted Anionic Cyclodextrins in Ball Milling
A number of influencing factors mean that the random substitution of cyclodextrins (CD) in solution is difficult to reproduce. Reaction assembly in mechanochemistry reduces the number of these factors. However, lack of water can improve the reaction outcomes by minimizing the reagent’s hydrolysis. H...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6155213/ https://www.ncbi.nlm.nih.gov/pubmed/28335503 http://dx.doi.org/10.3390/molecules22030485 |
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author | Jicsinszky, László Caporaso, Marina Calcio Gaudino, Emanuela Giovannoli, Cristina Cravotto, Giancarlo |
author_facet | Jicsinszky, László Caporaso, Marina Calcio Gaudino, Emanuela Giovannoli, Cristina Cravotto, Giancarlo |
author_sort | Jicsinszky, László |
collection | PubMed |
description | A number of influencing factors mean that the random substitution of cyclodextrins (CD) in solution is difficult to reproduce. Reaction assembly in mechanochemistry reduces the number of these factors. However, lack of water can improve the reaction outcomes by minimizing the reagent’s hydrolysis. High-energy ball milling is an efficient, green and simple method for one-step reactions and usually reduces degradation and byproduct formation. Anionic CD derivatives have successfully been synthesized in the solid state, using a planetary ball mill. Comparison with solution reactions, the solvent-free conditions strongly reduced the reagent hydrolysis and resulted in products of higher degree of substitution (DS) with more homogeneous DS distribution. The synthesis of anionic CD derivatives can be effectively performed under mechanochemical activation without significant changes to the substitution pattern but the DS distributions were considerably different from the products of solution syntheses. |
format | Online Article Text |
id | pubmed-6155213 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-61552132018-11-13 Synthesis of Randomly Substituted Anionic Cyclodextrins in Ball Milling Jicsinszky, László Caporaso, Marina Calcio Gaudino, Emanuela Giovannoli, Cristina Cravotto, Giancarlo Molecules Article A number of influencing factors mean that the random substitution of cyclodextrins (CD) in solution is difficult to reproduce. Reaction assembly in mechanochemistry reduces the number of these factors. However, lack of water can improve the reaction outcomes by minimizing the reagent’s hydrolysis. High-energy ball milling is an efficient, green and simple method for one-step reactions and usually reduces degradation and byproduct formation. Anionic CD derivatives have successfully been synthesized in the solid state, using a planetary ball mill. Comparison with solution reactions, the solvent-free conditions strongly reduced the reagent hydrolysis and resulted in products of higher degree of substitution (DS) with more homogeneous DS distribution. The synthesis of anionic CD derivatives can be effectively performed under mechanochemical activation without significant changes to the substitution pattern but the DS distributions were considerably different from the products of solution syntheses. MDPI 2017-03-19 /pmc/articles/PMC6155213/ /pubmed/28335503 http://dx.doi.org/10.3390/molecules22030485 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Jicsinszky, László Caporaso, Marina Calcio Gaudino, Emanuela Giovannoli, Cristina Cravotto, Giancarlo Synthesis of Randomly Substituted Anionic Cyclodextrins in Ball Milling |
title | Synthesis of Randomly Substituted Anionic Cyclodextrins in Ball Milling |
title_full | Synthesis of Randomly Substituted Anionic Cyclodextrins in Ball Milling |
title_fullStr | Synthesis of Randomly Substituted Anionic Cyclodextrins in Ball Milling |
title_full_unstemmed | Synthesis of Randomly Substituted Anionic Cyclodextrins in Ball Milling |
title_short | Synthesis of Randomly Substituted Anionic Cyclodextrins in Ball Milling |
title_sort | synthesis of randomly substituted anionic cyclodextrins in ball milling |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6155213/ https://www.ncbi.nlm.nih.gov/pubmed/28335503 http://dx.doi.org/10.3390/molecules22030485 |
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