Synthesis of well-controlled glycopolymers bearing oligosaccharides and their interactions with influenza viruses

Masanori Nagao, Yuuki Kurebayashi, Hirokazu Seto, Tomonari Tanaka, Tadanobu Takahashi, Takashi Suzuki, Yu Hoshino, Yoshiko Miura

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The synthesis of a series of glycopolymers bearing oligosaccharides using a 'post-click' chemistry strategy with an acrylamide (AAm) backbone was reported. The synthesized glycopolymers recognized the corresponding lectins, and poly(AAm-r-60-SALac) exhibited interactions with influenza viruses. AAm and trimethylsilyl propargyl acrylamide which has an alkyne moiety, were copolymerized by RAFT polymerization in dimethylsulfoxide. Several saccharides including two types of sialyllactoses were subjected to a one-step azidation reaction to afford the corresponding azide derivatives of the oligosaccharides without the need for a protection step. The terminals of the glycopolymer were reduced to thiol with NaBH4. The reduced glycopolymers were subsequently immobilized onto the SiO2-coated QCM cell surfaces. When the molar ratio of [TMS PrAAm] was greater than 20%, the percentage conversion values were less than 40%. Furthermore, an increase in the initial molar ratio of [TMS PrAAm] resulted in a decrease in the conversion. This result suggested that TMS PrAAm was an inappropriate substrate for radical polymerization reactions.

Original languageEnglish
Pages (from-to)745-749
Number of pages5
JournalPolymer Journal
Volume48
Issue number6
DOIs
Publication statusPublished - Jun 1 2016

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Bearings (structural)
Oligosaccharides
Acrylamide
Viruses
Free radical polymerization
Polyacrylates
Alkynes
Azides
Polymerization
Dimethyl Sulfoxide
Derivatives
Sulfhydryl Compounds
Lectins
Substrates

All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Materials Chemistry

Cite this

Synthesis of well-controlled glycopolymers bearing oligosaccharides and their interactions with influenza viruses. / Nagao, Masanori; Kurebayashi, Yuuki; Seto, Hirokazu; Tanaka, Tomonari; Takahashi, Tadanobu; Suzuki, Takashi; Hoshino, Yu; Miura, Yoshiko.

In: Polymer Journal, Vol. 48, No. 6, 01.06.2016, p. 745-749.

Research output: Contribution to journalArticle

Nagao, Masanori ; Kurebayashi, Yuuki ; Seto, Hirokazu ; Tanaka, Tomonari ; Takahashi, Tadanobu ; Suzuki, Takashi ; Hoshino, Yu ; Miura, Yoshiko. / Synthesis of well-controlled glycopolymers bearing oligosaccharides and their interactions with influenza viruses. In: Polymer Journal. 2016 ; Vol. 48, No. 6. pp. 745-749.
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AU - Suzuki, Takashi

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