Cargando…
Regioselective self-acylating cyclodextrins in organic solvent
Amphiphilic cyclodextrins have been synthesized with self-acylating reaction using vinyl esters in dimethylformamide. In the present study no base, catalyst, or enzyme was used, and the structural analyses using thin layer chromatography, nuclear magnetic resonance spectroscopy and mass spectrometry...
Autores principales: | , , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group
2016
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4810458/ https://www.ncbi.nlm.nih.gov/pubmed/27020946 http://dx.doi.org/10.1038/srep23740 |
_version_ | 1782423815639269376 |
---|---|
author | Cho, Eunae Yun, Deokgyu Jeong, Daham Im, Jieun Kim, Hyunki Dindulkar, Someshwar D. Choi, Youngjin Jung, Seunho |
author_facet | Cho, Eunae Yun, Deokgyu Jeong, Daham Im, Jieun Kim, Hyunki Dindulkar, Someshwar D. Choi, Youngjin Jung, Seunho |
author_sort | Cho, Eunae |
collection | PubMed |
description | Amphiphilic cyclodextrins have been synthesized with self-acylating reaction using vinyl esters in dimethylformamide. In the present study no base, catalyst, or enzyme was used, and the structural analyses using thin layer chromatography, nuclear magnetic resonance spectroscopy and mass spectrometry show that the cyclodextrin is substituted preferentially by one acyl moiety at the C2 position of the glucose unit, suggesting that cyclodextrin functions as a regioselective catalytic carbohydrate in organic solvent. In the self-acylation, the most acidic OH group at the 2-position and the inclusion complexing ability of cyclodextrin were considered to be significant. The substrate preference was also observed in favor of the long-chain acyl group, which could be attributed to the inclusion ability of cyclodextrin cavity. Furthermore, using the model amphiphilic building block, 2-O-mono-lauryl β-cyclodextrin, the self-organized supramolecular architecture with nano-vesicular morphology in water was investigated by fluorescence spectroscopy, dynamic light scattering and transmission electron microscopy. The cavity-type nano-assembled vesicle and the novel synthetic methods for the preparation of mono-acylated cyclodextrin should be of great interest with regard to drug/gene delivery systems, functional surfactants, and carbohydrate derivatization methods. |
format | Online Article Text |
id | pubmed-4810458 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Nature Publishing Group |
record_format | MEDLINE/PubMed |
spelling | pubmed-48104582016-04-04 Regioselective self-acylating cyclodextrins in organic solvent Cho, Eunae Yun, Deokgyu Jeong, Daham Im, Jieun Kim, Hyunki Dindulkar, Someshwar D. Choi, Youngjin Jung, Seunho Sci Rep Article Amphiphilic cyclodextrins have been synthesized with self-acylating reaction using vinyl esters in dimethylformamide. In the present study no base, catalyst, or enzyme was used, and the structural analyses using thin layer chromatography, nuclear magnetic resonance spectroscopy and mass spectrometry show that the cyclodextrin is substituted preferentially by one acyl moiety at the C2 position of the glucose unit, suggesting that cyclodextrin functions as a regioselective catalytic carbohydrate in organic solvent. In the self-acylation, the most acidic OH group at the 2-position and the inclusion complexing ability of cyclodextrin were considered to be significant. The substrate preference was also observed in favor of the long-chain acyl group, which could be attributed to the inclusion ability of cyclodextrin cavity. Furthermore, using the model amphiphilic building block, 2-O-mono-lauryl β-cyclodextrin, the self-organized supramolecular architecture with nano-vesicular morphology in water was investigated by fluorescence spectroscopy, dynamic light scattering and transmission electron microscopy. The cavity-type nano-assembled vesicle and the novel synthetic methods for the preparation of mono-acylated cyclodextrin should be of great interest with regard to drug/gene delivery systems, functional surfactants, and carbohydrate derivatization methods. Nature Publishing Group 2016-03-29 /pmc/articles/PMC4810458/ /pubmed/27020946 http://dx.doi.org/10.1038/srep23740 Text en Copyright © 2016, Macmillan Publishers Limited http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Article Cho, Eunae Yun, Deokgyu Jeong, Daham Im, Jieun Kim, Hyunki Dindulkar, Someshwar D. Choi, Youngjin Jung, Seunho Regioselective self-acylating cyclodextrins in organic solvent |
title | Regioselective self-acylating cyclodextrins in organic solvent |
title_full | Regioselective self-acylating cyclodextrins in organic solvent |
title_fullStr | Regioselective self-acylating cyclodextrins in organic solvent |
title_full_unstemmed | Regioselective self-acylating cyclodextrins in organic solvent |
title_short | Regioselective self-acylating cyclodextrins in organic solvent |
title_sort | regioselective self-acylating cyclodextrins in organic solvent |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4810458/ https://www.ncbi.nlm.nih.gov/pubmed/27020946 http://dx.doi.org/10.1038/srep23740 |
work_keys_str_mv | AT choeunae regioselectiveselfacylatingcyclodextrinsinorganicsolvent AT yundeokgyu regioselectiveselfacylatingcyclodextrinsinorganicsolvent AT jeongdaham regioselectiveselfacylatingcyclodextrinsinorganicsolvent AT imjieun regioselectiveselfacylatingcyclodextrinsinorganicsolvent AT kimhyunki regioselectiveselfacylatingcyclodextrinsinorganicsolvent AT dindulkarsomeshward regioselectiveselfacylatingcyclodextrinsinorganicsolvent AT choiyoungjin regioselectiveselfacylatingcyclodextrinsinorganicsolvent AT jungseunho regioselectiveselfacylatingcyclodextrinsinorganicsolvent |