"Click chemistry" on polysaccharides: A convenient, general, and monitorable approach to develop β-1,3-glucans with various functional appendages

Teruaki Hasegawa, Munenori Numata, Kazuo Sakurai, Seiji Shinkai

Research output: Contribution to conferencePaper

Abstract

β-1,3-glucans having various functional appendages (β-lactoside, ferrocene, pyrene, and porphyrin) can be prepared in a convenient, quantitative, and regioselective manner through regioselective bromination/azidation on curdlan to afford 6-azido-6-deoxy-curdlan followed by chemo-selective [3+2]cycloadditions with various functional modules with a terminal alkyn. In addition to the aforementioned advantages, monitorablity is an additional advantage of this synthetic approach over the conventional direct modifications on polysaccharides, that is, the reaction can be easily monitored based on intensity of azido-peaks in in situ attenuated total reflection-infrared spectra. The resultant curdlan derivatives, especially that having lactoside-appendages, can interact with certain polynucleotides to form stable macromolecular complex that can bind to RCA120 (β-lactoside recognition lectin).

Original languageEnglish
Pages4895-4896
Number of pages2
Publication statusPublished - Dec 1 2005
Event54th SPSJ Symposium on Macromolecules - Yamagata, Japan
Duration: Sep 20 2005Sep 22 2005

Other

Other54th SPSJ Symposium on Macromolecules
CountryJapan
CityYamagata
Period9/20/059/22/05

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Addition reactions
Cycloaddition
Pyrene
Alkylation
Porphyrins
Polysaccharides
Complexation
Macromolecules
Molecular structure
Infrared spectroscopy
Infrared radiation
Derivatives
Polynucleotides
Lectins

All Science Journal Classification (ASJC) codes

  • Engineering(all)

Cite this

Hasegawa, T., Numata, M., Sakurai, K., & Shinkai, S. (2005). "Click chemistry" on polysaccharides: A convenient, general, and monitorable approach to develop β-1,3-glucans with various functional appendages. 4895-4896. Paper presented at 54th SPSJ Symposium on Macromolecules, Yamagata, Japan.

"Click chemistry" on polysaccharides : A convenient, general, and monitorable approach to develop β-1,3-glucans with various functional appendages. / Hasegawa, Teruaki; Numata, Munenori; Sakurai, Kazuo; Shinkai, Seiji.

2005. 4895-4896 Paper presented at 54th SPSJ Symposium on Macromolecules, Yamagata, Japan.

Research output: Contribution to conferencePaper

Hasegawa, T, Numata, M, Sakurai, K & Shinkai, S 2005, '"Click chemistry" on polysaccharides: A convenient, general, and monitorable approach to develop β-1,3-glucans with various functional appendages' Paper presented at 54th SPSJ Symposium on Macromolecules, Yamagata, Japan, 9/20/05 - 9/22/05, pp. 4895-4896.
Hasegawa T, Numata M, Sakurai K, Shinkai S. "Click chemistry" on polysaccharides: A convenient, general, and monitorable approach to develop β-1,3-glucans with various functional appendages. 2005. Paper presented at 54th SPSJ Symposium on Macromolecules, Yamagata, Japan.
Hasegawa, Teruaki ; Numata, Munenori ; Sakurai, Kazuo ; Shinkai, Seiji. / "Click chemistry" on polysaccharides : A convenient, general, and monitorable approach to develop β-1,3-glucans with various functional appendages. Paper presented at 54th SPSJ Symposium on Macromolecules, Yamagata, Japan.2 p.
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