Carbohydrate-appended curdlans as a new family of glycoclusters with binding properties both for a polynucleotide and lectins

Teruaki Hasegawa, Munenori Numata, Shiro Okumura, Taro Kimura, Kazuo Sakurai, Seiji Shinkai

Research output: Contribution to journalArticlepeer-review

61 Citations (Scopus)

Abstract

β-1,3-Glucans having carbohydrate-appendages (α-d-mannoside, N-acetyl-β-d-glucosaminide and β-lactoside) at the C6-position of every repeating unit can be readily prepared from curdlan (a linear β-1,3-glucan) through regioselective bromination/azidation to afford 6-azido-6-deoxycurdlan followed by chemo-selective Cu(i)-catalyzed [3 + 2]-cycloaddition with various carbohydrate modules having a terminal alkyne. The resultant carbohydrate-appended curdlans can interact with polycytosine to form stable macromolecular complexes consistent with two polysaccharide strands and one polycytosine strand. Furthermore, these macromolecular complexes show strong and specific affinity toward carbohydrate-binding proteins (lectins). Therefore, one can utilize these carbohydrate-appended curdlans as a new family of glycoclusters.

Original languageEnglish
Pages (from-to)2404-2412
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume5
Issue number15
DOIs
Publication statusPublished - Jan 1 2007

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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