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Chemical Synthesis of Residue-Selectively C and H Double-Isotope-Labeled Oligosaccharides as Chemical Probes for the NMR-Based Conformational Analysis of Oligosaccharides. | LitMetric

AI Article Synopsis

  • The analysis of oligosaccharide shapes is key in glycobiology, and using NMR with atom-selectively C-labeled oligosaccharides gives more detailed insights into their structures.
  • Traditional non-labeled oligosaccharides lack the depth of information provided by labeled ones, which can be limited in scope.
  • This study introduces the synthesis of residue-selectively C- and H-labeled oligosaccharides, enhancing NMR measurements to reveal important information on their conformations, specifically in β(1,3)-glucan oligosaccharides.

Article Abstract

The conformational analysis of oligosaccharide is a fundamental issue in glycobiology. NMR measurements of atom-selectively C-labeled oligosaccharides have provided valuable information concerning their conformation, which would not be possible using nonlabeled oligosaccharides. The amount of accessible information from an atom-selectively labeled molecule, however, is limited. In this work, we report on the chemical synthesis of residue-selectively C- and H-labeled oligosaccharides and their use in conformational analysis. H NMR measurements of such double isotope-labeled compounds can provide a great deal of information on the dihedral angles across glycosidic linkages. We demonstrated this method in the conformational analyses of some linear and branched β(1,3)-glucan oligosaccharides.

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Source
http://dx.doi.org/10.1021/acs.joc.0c01939DOI Listing

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