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

ChemistryOpen
Shoichi NishitaniToshiya Sakata

Abstract

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 (C1 and C2) of β-SA but not α-SA. Moreover, the facts that the C2 atom is blocked by a glycoside bond in a physiological environmen...Continue Reading

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Citations

Mar 14, 2020·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·Solomon A MensahEno E Ebong
Dec 19, 2019·Langmuir : the ACS Journal of Surfaces and Colloids·Wenfeng HaiWenming Wu

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Methods Mentioned

BETA
NMR
biosensor

Software Mentioned

MP2
GIAO
Delta NMR
Winmostar
Gaussian

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