'Click chemistry' on polysaccharides: A convenient, general, and monitorable approach to develop (1→3)-β-d-glucans with various functional appendages

Teruaki Hasegawa, Mariko Umeda, Munenori Numata, Chun Li, Ah Hyun Bae, Tomohisa Fujisawa, Shuichi Haraguchi, Kazuo Sakurai, Seiji Shinkai

Research output: Contribution to journalArticlepeer-review

109 Citations (Scopus)

Abstract

(1→3)-β-d-Glucans having various functional appendages (lactoside, ferrocene, pyrene, and porphyrin) can be prepared in an convenient, quantitative, and regioselective manner through regioselective bromination-azidation of curdlan to afford 6-azido-6-deoxycurdlan followed by chemoselective [3+2]-cycloadditions with various functional modules bearing a terminal alkyne group. The ability to monitor reaction conversions is an additional advantage of this synthetic approach over the conventional direct modifications on polysaccharides; the reaction can be readily monitored based on the intensity of azido peaks in the in situ attenuated total reflection infrared spectra.

Original languageEnglish
Pages (from-to)35-40
Number of pages6
JournalCarbohydrate Research
Volume341
Issue number1
DOIs
Publication statusPublished - Jan 16 2006

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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