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Understanding the Molecular Structure of the Sialic Acid–Phenylboronic Acid Complex by using a Combined NMR Spectroscopy and DFT Study: Toward Sialic Acid Detection at Cell Membranes
The origin of the unusually high stability of the sialic acid (SA) and phenylboronic acid (PBA) complex was investigated by a combined nuclear magnetic resonance (NMR) spectroscopy and density functional theory (DFT) study. SA is a glycan‐terminating monosaccharide, and its importance as a clinical...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6031860/ https://www.ncbi.nlm.nih.gov/pubmed/30003005 http://dx.doi.org/10.1002/open.201800071 |
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author | Nishitani, Shoichi Maekawa, Yuki Sakata, Toshiya |
author_facet | Nishitani, Shoichi Maekawa, Yuki Sakata, Toshiya |
author_sort | Nishitani, Shoichi |
collection | PubMed |
description | The origin of the unusually high stability of the sialic acid (SA) and phenylboronic acid (PBA) complex was investigated by a combined nuclear magnetic resonance (NMR) spectroscopy and density functional theory (DFT) study. SA is a glycan‐terminating monosaccharide, and its importance as a clinical target has long been recognized. Inspired by the fact that the binding properties of SA–PBA complexation are anomalously high relative to those of typical monosaccharides, great effort has been made to build a clinical platform with the use of PBA as a SA‐selective receptor. Although a number of applications have been reported in recent years, the ability of PBA to recognize SA‐terminating surface glycans selectively is still unclear, because high‐affinity SA–PBA complexation might not occur in a physiological environment. In particular, different forms of SA (α‐ and β‐pyranose) were not considered in detail. To answer this question, the combined NMR spectroscopy/DFT study revealed that the advantageous binding properties of the SA–PBA complex arise from ester bonding involving the α‐carboxylate moieties (C(1) and C(2)) of β‐SA but not α‐SA. Moreover, the facts that the C(2) atom is blocked by a glycoside bond in a physiological environment and that α‐SA basically exists on membrane‐bound glycans in a physiological environment lead to the conclusion that PBA cannot selectively recognize the SA unit to discriminate specific types of cells. Our results have a significant impact on the field of SA‐based cell recognition. |
format | Online Article Text |
id | pubmed-6031860 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-60318602018-07-12 Understanding the Molecular Structure of the Sialic Acid–Phenylboronic Acid Complex by using a Combined NMR Spectroscopy and DFT Study: Toward Sialic Acid Detection at Cell Membranes Nishitani, Shoichi Maekawa, Yuki Sakata, Toshiya ChemistryOpen Full Papers The origin of the unusually high stability of the sialic acid (SA) and phenylboronic acid (PBA) complex was investigated by a combined nuclear magnetic resonance (NMR) spectroscopy and density functional theory (DFT) study. SA is a glycan‐terminating monosaccharide, and its importance as a clinical target has long been recognized. Inspired by the fact that the binding properties of SA–PBA complexation are anomalously high relative to those of typical monosaccharides, great effort has been made to build a clinical platform with the use of PBA as a SA‐selective receptor. Although a number of applications have been reported in recent years, the ability of PBA to recognize SA‐terminating surface glycans selectively is still unclear, because high‐affinity SA–PBA complexation might not occur in a physiological environment. In particular, different forms of SA (α‐ and β‐pyranose) were not considered in detail. To answer this question, the combined NMR spectroscopy/DFT study revealed that the advantageous binding properties of the SA–PBA complex arise from ester bonding involving the α‐carboxylate moieties (C(1) and C(2)) of β‐SA but not α‐SA. Moreover, the facts that the C(2) atom is blocked by a glycoside bond in a physiological environment and that α‐SA basically exists on membrane‐bound glycans in a physiological environment lead to the conclusion that PBA cannot selectively recognize the SA unit to discriminate specific types of cells. Our results have a significant impact on the field of SA‐based cell recognition. John Wiley and Sons Inc. 2018-07-02 /pmc/articles/PMC6031860/ /pubmed/30003005 http://dx.doi.org/10.1002/open.201800071 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Full Papers Nishitani, Shoichi Maekawa, Yuki Sakata, Toshiya Understanding the Molecular Structure of the Sialic Acid–Phenylboronic Acid Complex by using a Combined NMR Spectroscopy and DFT Study: Toward Sialic Acid Detection at Cell Membranes |
title | Understanding the Molecular Structure of the Sialic Acid–Phenylboronic Acid Complex by using a Combined NMR Spectroscopy and DFT Study: Toward Sialic Acid Detection at Cell Membranes |
title_full | Understanding the Molecular Structure of the Sialic Acid–Phenylboronic Acid Complex by using a Combined NMR Spectroscopy and DFT Study: Toward Sialic Acid Detection at Cell Membranes |
title_fullStr | Understanding the Molecular Structure of the Sialic Acid–Phenylboronic Acid Complex by using a Combined NMR Spectroscopy and DFT Study: Toward Sialic Acid Detection at Cell Membranes |
title_full_unstemmed | Understanding the Molecular Structure of the Sialic Acid–Phenylboronic Acid Complex by using a Combined NMR Spectroscopy and DFT Study: Toward Sialic Acid Detection at Cell Membranes |
title_short | Understanding the Molecular Structure of the Sialic Acid–Phenylboronic Acid Complex by using a Combined NMR Spectroscopy and DFT Study: Toward Sialic Acid Detection at Cell Membranes |
title_sort | understanding the molecular structure of the sialic acid–phenylboronic acid complex by using a combined nmr spectroscopy and dft study: toward sialic acid detection at cell membranes |
topic | Full Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6031860/ https://www.ncbi.nlm.nih.gov/pubmed/30003005 http://dx.doi.org/10.1002/open.201800071 |
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