'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 journalArticle

106 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

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Bearings (structural)
Click Chemistry
Conversion Disorder
Aptitude
Alkynes
Glucans
Cycloaddition
Halogenation
Porphyrins
Cycloaddition Reaction
Polysaccharides
Infrared radiation
ferrocene
curdlan
lactosides
pyrene

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this

'Click chemistry' on polysaccharides : A convenient, general, and monitorable approach to develop (1→3)-β-d-glucans with various functional appendages. / Hasegawa, Teruaki; Umeda, Mariko; Numata, Munenori; Li, Chun; Bae, Ah Hyun; Fujisawa, Tomohisa; Haraguchi, Shuichi; Sakurai, Kazuo; Shinkai, Seiji.

In: Carbohydrate Research, Vol. 341, No. 1, 16.01.2006, p. 35-40.

Research output: Contribution to journalArticle

Hasegawa, Teruaki ; Umeda, Mariko ; Numata, Munenori ; Li, Chun ; Bae, Ah Hyun ; Fujisawa, Tomohisa ; Haraguchi, Shuichi ; Sakurai, Kazuo ; Shinkai, Seiji. / 'Click chemistry' on polysaccharides : A convenient, general, and monitorable approach to develop (1→3)-β-d-glucans with various functional appendages. In: Carbohydrate Research. 2006 ; Vol. 341, No. 1. pp. 35-40.
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