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Synthesis and conformational analysis of poly(phenylacetylene)s with serinol-tethered carbohydrate appendages.

Authors
  • Masubuchi, Kana1
  • Maehata, Masakiyo1
  • Suzuki, Chieko1
  • Matsuoka, Ryoji2
  • Sekiguchi, Maki1
  • Chigira, Naoto2
  • Amano, Yoshitsugu2
  • Inokuchi, Mayu1
  • Li, Qintong1
  • Hasegawa, Teruaki3
  • 1 Faculty of Life Sciences, Toyo University, 1-1-1 Izumino, Itakura-machi, Ora-gun, Gumma, 374-0193, Japan. , (Japan)
  • 2 Graduate School of Life Sciences, Toyo University, 1-1-1 Izumino, Itakura-machi, Ora-gun, Gumma, 374-0193, Japan. , (Japan)
  • 3 Faculty of Life Sciences, Toyo University, 1-1-1 Izumino, Itakura-machi, Ora-gun, Gumma, 374-0193, Japan; Bio-Nano Electronics Research Centre, Toyo University, 2100 Kujirai, Kawagoe, Saitama, 350-8585, Japan. Electronic address: [email protected] , (Japan)
Type
Published Article
Journal
Carbohydrate research
Publication Date
Jul 15, 2019
Volume
481
Pages
23–30
Identifiers
DOI: 10.1016/j.carres.2019.06.002
PMID: 31220628
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

We synthesized phenylacetylenes containing β-lactoside, β-cellobioside, or β-maltoside, and polymerized them to produce the corresponding poly (phenylacetylene)s. In these poly (phenylacetylene)s, the pendent carbohydrates were tethered to the mainchains by serinol spacers. Because similar glycosyl serinol units are found in the natural glycosphingolipids in cell membranes, the densely packed carbohydrate clusters along the poly (phenylacetylene) mainchains act as molecular mimics of cell surface glycoclusters. We analyzed the conformation of the glycosylated poly (phenylacetylene)s using circular dichroism spectroscopy, and found that the spatial carbohydrate packing within the glycoclusters changed on the addition of salts. Copyright © 2019 Elsevier Ltd. All rights reserved.

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