Photoactivatable crosslinking sugars for capturing glycoprotein interactions

Yoshihito Tanaka, Jennifer J. Kohler

Research output: Contribution to journalArticle

101 Scopus citations

Abstract

Carbohydrates are key mediators of cell-cell, cell-virus, and cell-ligand interactions. These interactions are often difficult to study because they are characterized by fast off rates and low affinities. Photoactivatable crosslinking sugars can be used to capture these transient interactions by forming a covalent bond between the carbohydrate and its binding partner. We designed and synthesized "photo-sugars" that contain diazirine moieties on the N-acyl side chains. We demonstrated that these photo-sugars could be metabolically incorporated onto the surface of living cells. Upon UV irradiation, specific crosslinks were formed between glycoprotein binding partners. Importantly, photo-sugar incorporation competes efficiently with endogenous carbohydrate biosynthesis and is compatible with the sialic acid modifications, such as 9-O-acetylation, that regulate binding events.

Original languageEnglish (US)
Pages (from-to)3278-3279
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number11
DOIs
StatePublished - Mar 19 2008

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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