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Inter-residual Hydrogen Bonding in Carbohydrates Unraveled by NMR Spectroscopy and Molecular Dynamics Simulations
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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Number of Authors: 62019 (English)In: ChemBioChem (Print), ISSN 1439-4227, E-ISSN 1439-7633, Vol. 20, p. 2519-2528Article in journal (Refereed) Published
Abstract [en]

Carbohydrates, also known as glycans in biological systems, are omnipresent in nature where they as glycoconjugates occur as oligo- and polysaccharides linked to lipids and proteins. Their three-dimensional structure is defined by two or three torsion angles at each glycosidic linkage. In addition, transglycosidic hydrogen bonding between sugar residues may be important. Herein we investigate the presence of these inter-residue interactions by NMR spectroscopy in D2O/[D-6]DMSO (70:30) or D2O and by molecular dynamics (MD) simulations with explicit water as solvent for disaccharides with structural elements alpha-d-Manp-(1 -> 2)-d-Manp, beta-d-GlcpNAc-(1 -> 2)-d-Manp, and alpha-d-Glcp-(1 -> 4)-beta-d-Glcp, all of which have been suggested to exhibit inter-residue hydrogen bonding. For the disaccharide beta-d-GlcpNAc-(1 -> 2)-beta-d-Manp-OMe, the large extent of O5 '...HO3 hydrogen bonding as seen from the MD simulation is implicitly supported by the H-1 NMR chemical shift and (3)J(HO3,H3) value of the hydroxy proton. In the case of alpha-d-Glcp-(1 -> 4)-beta-d-Glcp-OMe, the existence of a transglycosidic hydrogen bond O2 '...HO3 was proven by the presence of a cross-peak in H-1,C-13 HSQC-TOCSY experiments as a result of direct TOCSY transfer between HO3 of the reducing end residue and H2 ' (detected at C2 ') of the terminal residue. The occurrence of inter-residue hydrogen bonding, albeit transient, is judged important for the stabilization of three-dimensional structures, which may be essential in maintaining a conformational state for carbohydrate-protein interactions of glycans to take place in biologically important environments.

Place, publisher, year, edition, pages
2019. Vol. 20, p. 2519-2528
Keywords [en]
amylose, disaccharides, glycans, O-methyl groups, transient hydrogen bonds
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-175104DOI: 10.1002/cbic.201900301ISI: 000484055100001PubMedID: 31066963OAI: oai:DiVA.org:su-175104DiVA, id: diva2:1362821
Available from: 2019-10-21 Created: 2019-10-21 Last updated: 2019-10-21Bibliographically approved

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Rönnols, JerkEngström, OlofSäwén, ElinWidmalm, Göran
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