The development of new molecular tools containing a chemically synthesized carbohydrate ligand for the elucidation of carbohydrate roles via photoaffinity labeling: Carbohydrate-protein interactions are affected by the structures of the glycosidic bonds and the reducing-end sugar

Isao Ohtsuka, Yutaka Sadakane, Noriyasu Hada, Mari Higuchi, Toshiyuki Atsumi, Nobuko Kakiuchi

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Photoaffinity labeling technology is a highly efficient method for cloning carbohydrate-binding proteins. When the carbohydrate probes are synthesized according to conventional methods, however, the reducing terminus of the sugar is opened to provide an acyclic structure. Our continued efforts to solve this problem led to the development of new molecular tools with an oligosaccharide structure that contains a phenyldiazirine group for the elucidation of carbohydrate-protein interactions. We investigated whether carbohydrate-lectin interactions are affected by differences in the glycosidic formation and synthesized three types of molecular tools containing Galp-GlcpNAc disaccharide ligands and a photoreactive group (1, 2, 3). Photoaffinity labeling validated the recognition of the new ligand by different glycosidic bonds. Photoaffinity labeling also demonstrated that both the reducing end sugar and non-reducing end sugar recognized the Erythrina cristagalli agglutinin.

Original languageEnglish
Pages (from-to)3829-3837
Number of pages9
JournalBioorganic and Medicinal Chemistry
Volume22
Issue number15
DOIs
Publication statusPublished - 2014 Aug 1

Keywords

  • Carbohydrate-lectin interactions
  • Different glycosidic bonds
  • Molecular tool
  • Oligosaccharide synthesis
  • Photoaffinity labeling

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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