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Separation of saccharides using fullerene-bonded silica monolithic columns via π interactions in liquid chromatography

We report on a potential method to separate sugars by using the specific interaction between fullerenes and saccharides in liquid chromatography (LC). Aromatic rings with high electron density are believed to interact strongly with saccharides due to CH–π and/or OH–π interactions. In this study, the...

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Autores principales: Kobayashi, Hiroshi, Okada, Kazuya, Tokuda, Shinnosuke, Kanao, Eisuke, Masuda, Yusuke, Naito, Toyohiro, Takaya, Hikaru, Yan, Mingdi, Kubo, Takuya, Otsuka, Koji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7429847/
https://www.ncbi.nlm.nih.gov/pubmed/32796903
http://dx.doi.org/10.1038/s41598-020-70904-3
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author Kobayashi, Hiroshi
Okada, Kazuya
Tokuda, Shinnosuke
Kanao, Eisuke
Masuda, Yusuke
Naito, Toyohiro
Takaya, Hikaru
Yan, Mingdi
Kubo, Takuya
Otsuka, Koji
author_facet Kobayashi, Hiroshi
Okada, Kazuya
Tokuda, Shinnosuke
Kanao, Eisuke
Masuda, Yusuke
Naito, Toyohiro
Takaya, Hikaru
Yan, Mingdi
Kubo, Takuya
Otsuka, Koji
author_sort Kobayashi, Hiroshi
collection PubMed
description We report on a potential method to separate sugars by using the specific interaction between fullerenes and saccharides in liquid chromatography (LC). Aromatic rings with high electron density are believed to interact strongly with saccharides due to CH–π and/or OH–π interactions. In this study, the fullerene-bonded columns were used to separate saccharides by LC under aqueous conditions. As a result, 2-aminobenzamide-labeled glucose homopolymer (Glcs) was effectively separated by both C60 and C70 columns in the range of Glc-1 to Glc-20 and high blood glucose level being retained in greater quantity. Furthermore, similar separations were identified by LC–mass spectrometry with non-labeled glucose homopolymers. Theoretical study based on molecular dynamics and DFT calculation demonstrated that a supramolecular complex of saccharide–fullerene was formed through CH–π and/or OH–π interactions, and that the interactions between saccharide and fullerene increase with the increase units of the saccharide. Additionally, the C60 column retained disaccharides containing maltose, trehalose, and sucrose. In this case, it was assumed that the retention rates were determined by the difference of the dipole moment in each saccharide. These results suggest that the dipole-induced dipole interaction was dominant, and that maltose—with the higher dipole moment—was more strongly retained compared to other disaccharides having lower dipole moment.
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spelling pubmed-74298472020-08-18 Separation of saccharides using fullerene-bonded silica monolithic columns via π interactions in liquid chromatography Kobayashi, Hiroshi Okada, Kazuya Tokuda, Shinnosuke Kanao, Eisuke Masuda, Yusuke Naito, Toyohiro Takaya, Hikaru Yan, Mingdi Kubo, Takuya Otsuka, Koji Sci Rep Article We report on a potential method to separate sugars by using the specific interaction between fullerenes and saccharides in liquid chromatography (LC). Aromatic rings with high electron density are believed to interact strongly with saccharides due to CH–π and/or OH–π interactions. In this study, the fullerene-bonded columns were used to separate saccharides by LC under aqueous conditions. As a result, 2-aminobenzamide-labeled glucose homopolymer (Glcs) was effectively separated by both C60 and C70 columns in the range of Glc-1 to Glc-20 and high blood glucose level being retained in greater quantity. Furthermore, similar separations were identified by LC–mass spectrometry with non-labeled glucose homopolymers. Theoretical study based on molecular dynamics and DFT calculation demonstrated that a supramolecular complex of saccharide–fullerene was formed through CH–π and/or OH–π interactions, and that the interactions between saccharide and fullerene increase with the increase units of the saccharide. Additionally, the C60 column retained disaccharides containing maltose, trehalose, and sucrose. In this case, it was assumed that the retention rates were determined by the difference of the dipole moment in each saccharide. These results suggest that the dipole-induced dipole interaction was dominant, and that maltose—with the higher dipole moment—was more strongly retained compared to other disaccharides having lower dipole moment. Nature Publishing Group UK 2020-08-14 /pmc/articles/PMC7429847/ /pubmed/32796903 http://dx.doi.org/10.1038/s41598-020-70904-3 Text en © The Author(s) 2020 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Kobayashi, Hiroshi
Okada, Kazuya
Tokuda, Shinnosuke
Kanao, Eisuke
Masuda, Yusuke
Naito, Toyohiro
Takaya, Hikaru
Yan, Mingdi
Kubo, Takuya
Otsuka, Koji
Separation of saccharides using fullerene-bonded silica monolithic columns via π interactions in liquid chromatography
title Separation of saccharides using fullerene-bonded silica monolithic columns via π interactions in liquid chromatography
title_full Separation of saccharides using fullerene-bonded silica monolithic columns via π interactions in liquid chromatography
title_fullStr Separation of saccharides using fullerene-bonded silica monolithic columns via π interactions in liquid chromatography
title_full_unstemmed Separation of saccharides using fullerene-bonded silica monolithic columns via π interactions in liquid chromatography
title_short Separation of saccharides using fullerene-bonded silica monolithic columns via π interactions in liquid chromatography
title_sort separation of saccharides using fullerene-bonded silica monolithic columns via π interactions in liquid chromatography
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7429847/
https://www.ncbi.nlm.nih.gov/pubmed/32796903
http://dx.doi.org/10.1038/s41598-020-70904-3
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