New Glycotechnology Exploiting 1,2-Glycosidic Polymer

• Project/Area Number: 17H03070
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Polymer chemistry
• Research Institution: Toyama Prefectural University
• Principal Investigator: Koyama Yasuhito 富山県立大学, 工学部, 准教授 (10456262)
• Project Period (FY): 2017-04-01 – 2020-03-31
• Project Status: Completed (Fiscal Year 2019)
• Budget Amount: ¥17,680,000 (Direct Cost: ¥13,600,000、Indirect Cost: ¥4,080,000); Fiscal Year 2019: ¥6,370,000 (Direct Cost: ¥4,900,000、Indirect Cost: ¥1,470,000); Fiscal Year 2018: ¥7,540,000 (Direct Cost: ¥5,800,000、Indirect Cost: ¥1,740,000); Fiscal Year 2017: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
• Keywords: 糖鎖 / 高分子合成 / 生体分子 / 自己組織化 / 超分子化学

Outline of Final Research Achievements

This work was aimed to manipulate the properties of bioactive natural glycosides and to create high performance polymers and biomaterials exploiting 1,2-glycosidic polymer as a scaffold. We investigated (i) the development of modification method of 1,2-glycosidic polymer, (i) the elucidation of dynamic structure of the polymer single chain, and (iii) the evaluation of the phisical properties of new materials. Through the comparison of properties with those of the other polysaccharides, we evaluated the impact of glycosidic position on the properties of polysaccharides.

Academic Significance and Societal Importance of the Research Achievements

本研究は糖鎖化学で欠落していた1,2-グリコシド型ポリマーについて研究したため、糖の重合位置・構造が糖鎖の高次構造に及ぼす効果を体系的に理解できるようになると期待され、糖鎖化学の観点からも重要な成果であると考えている。糖鎖は様々な研究分野で取り扱われる標的分子であり、新材料を目指す研究だけでなく、基礎化学、医療、製薬分野において極めて重要な分子群である。そのため、本研究で合成した糖鎖は、糖鎖の全研究分野で縦断的に利用される有用なライブラリーになると期待される。

Research Products

• [Journal Article] Bolaamphiphilic properties and pH-dependent micellization of quercetin polyglycoside (2019)
  • Author(s): Mahmuda Nargis, Abu Bin Ihsan, Yasuhito Koyama
  • Journal Title: RSC Advances Volume: 9 Issue: 58 Pages: 33674-33677
  • DOI: 10.1039/c9ra05711k
  • Peer Reviewed / Open Access
• [Journal Article] Structural factors of benzylated glucopyranans for shear-induced adhesion (2019)
  • Author(s): Abu Bin Ihsan, Yuta Kawaguchi, Hiromichi Inokuchi, Hiroshi Endo, Yasuhito Koyama
  • Journal Title: RSC Advances Volume: 9 Issue: 45 Pages: 26214-26218
  • DOI: 10.1039/c9ra02644d
  • Peer Reviewed / Open Access
• [Journal Article] Effects of the hydrophilic-lipophilic balance of alternating peptides on self-assembly and thermo-responsive behaviors (2019)
  • Author(s): Abu Bin Ihsan, Mahmuda Nargis, Yasuhito Koyama
  • Journal Title: International Journal of Molecular Sciences Volume: 20 Issue: 18 Pages: 4604-4604
  • DOI: 10.3390/ijms20184604
  • Peer Reviewed / Open Access
• [Journal Article] Strong, tough, and repeatable adhesion of an alternating peptide comprising phenyl glycine as a repeating unit (2019)
  • Author(s): Abu Bin Ihsan, Yuta Kawaguchi, Hiroshi Endo, Yasuhito Koyama
  • Journal Title: Journal of Material Chemistry B Volume: 7 Issue: 17 Pages: 2766-2770
  • DOI: 10.1039/c9tb00391f
  • Peer Reviewed
• [Journal Article] Effects of 2,5-furanylene sulfides in polymer main chains on polymer physical properties (2019)
  • Author(s): Abu Bin Ihsan, Yasuhiro Tawara, Shinya Goto, Hirokazu Kobayashi, Kiyotaka Nakajima, Atsushi Fukuoka, Yasuhito Koyama
  • Journal Title: Polymer Journal Volume: 51 Issue: 4 Pages: 413-422
  • DOI: 10.1038/s41428-018-0140-9
  • NAID: 40021935832
  • Peer Reviewed
• [Journal Article] Impact of polypeptide sequence on thermal properties for diblock, random, and alternating copolymers containing a stoichiometric mixture of glycine and valine (2019)
  • Author(s): Abu Bin Ihsan, Yasuhito Koyama
  • Journal Title: Polymer Volume: 161 Pages: 197-204
  • DOI: 10.1016/j.polymer.2018.12.021
  • Peer Reviewed
• [Journal Article] Development of regenerated silk films coated with fluorinated polypeptides to achieve high water repellency and biodegradability in seqwater (2019)
  • Author(s): Kousuke Tsuchiya, Nao Ifuku, Yasuhito Koyama, Keiji Numata
  • Journal Title: Polymer Degradation and Stability Volume: 160 Pages: 96-101
  • DOI: 10.1016/j.polymdegradstab.2018.12.016
  • Peer Reviewed
• [Journal Article] オリゴ糖の直接導入を可能とする(1→2)グルコピラナンのグラフト法の開発 (2019)
  • Author(s): 小山靖人
  • Journal Title: Cellulose Communications Volume: 26 Pages: 14-18
  • NAID: 40021826131
• [Journal Article] Direct grafting reactions of thermo-responsive (1→2)-glucopyranan derivatives using a sugar-based cyclic sulfite as monomer (2018)
  • Author(s): Sangeetha Srinivasa Shetty, Abu Bin Ihsan, Yasutomo Masugata, Yasuhito Koyama*
  • Journal Title: Chemistry Letters Volume: 47 Issue: 11 Pages: 1375-1378
  • DOI: 10.1246/cl.180650
  • NAID: 130007504949
  • Peer Reviewed
• [Journal Article] Thermo-responsive structure and surface activity of kinetically stabilized micelle composed of fluorinated alternating peptides in organic solvent (2018)
  • Author(s): Abu Bin Ihsan, Yasuhito Koyama,* Toshiaki Taira, Tomohiro Imura
  • Journal Title: ChemistrySelect Volume: 3 Issue: 16 Pages: 4173-4178
  • DOI: 10.1002/slct.201800590
  • Peer Reviewed
• [Journal Article] Fluorinated polymer surfactants bearing an alternating peptide skeleton prepared by three-component polycondensation (2018)
  • Author(s): Yasuhito Koyama,* Abu Bin Ihsan, Toshiaki Taira, Tomohiro Imura
  • Journal Title: RSC Advances Volume: 8 Issue: 14 Pages: 7509-7513
  • DOI: 10.1039/c8ra00581h
  • Peer Reviewed / Open Access
• [Journal Article] Synthetic approach of thermally tunable nature-mimetic polypeptides from N-protected alternating peptoids (2018)
  • Author(s): Yasuhito Koyama,* Abu Bin Ihsan, Prashant Gopal Gudeangadi
  • Journal Title: Macromolecular Chemistry and Physics Volume: 219 Issue: 19
  • DOI: 10.1002/macp.201800303
  • Peer Reviewed
• [Journal Article] Induction of Single-Handed Helicity of Polyacetylenes Using Mechanically Chiral Rotaxanes as Chiral Sources (2017)
  • Author(s): Ishiwari Fumitaka、Nakazono Kazuko、Koyama Yasuhito、Takata Toshikazu
  • Journal Title: Angewandte Chemie International Edition Volume: 56 Issue: 47 Pages: 14858-14862
  • DOI: 10.1002/anie.201707926
  • Peer Reviewed
• [Journal Article] One-pot synthesis of alternating peptides exploiting a new polymerization technique based on Ugi's 4CC reaction (2017)
  • Author(s): Y. Koyama, P. G. Gudeangadi
  • Journal Title: Chemical Communications Volume: 53 Issue: 27 Pages: 3846-3849
  • DOI: 10.1039/c6cc09379e
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Synthesis and properties of rotaxane-cross-linked polymers using a double-stranded γ-CD-based inclusion complex as a supramolecular cross-linker (2017)
  • Author(s): K. Jang, K. Iijima, Y. Koyama, S. Uchida, S. Asai, T. Takata
  • Journal Title: Polymer Volume: 印刷中 Pages: 379-385
  • DOI: 10.1016/j.polymer.2017.01.062
  • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
• [Presentation] 天然配糖体のミセル化挙動における糖鎖の影響 (2020)
  • Author(s): 宮﨑 凌, M. Nargis, A. B. Ihsan, 小山靖人
  • Organizer: 日本化学会第100春季年会
• [Presentation] グリチルレチン酸誘導体と発光性金属錯体の複合化による特異的ナノ構造の創製とその機能 (2019)
  • Author(s): チャン テイ ジウ ヒエン、小山靖人、黒岩敬太
  • Organizer: 第68回高分子学会年次大会
• [Presentation] ケルセチン多糖配糖体からなるミセルのpH依存性 (2019)
  • Author(s): M. Nargis, A. B. Ihsan, Y. Koyama
  • Organizer: 2019年度有機合成化学北陸セミナー
• [Presentation] 開環重合によるケルセチン多糖配糖体の合成とそのミセル化挙動 (2019)
  • Author(s): M. Nargis, A. B. Ihsan, Y. Koyama
  • Organizer: 第68回高分子学会北陸支部研究発表会
• [Presentation] Structural Effects of (1→2)-Glucopyranan on Shear-Induced Adhesion (2019)
  • Author(s): A. B. Ihsan, Y. Koyama
  • Organizer: 第30回エラストマー討論会
• [Presentation] Surface Saccharification and Thermo-Responsive Behaviors of (1→2)-Glucopyranan (2018)
  • Author(s): Abu Bin Ihsan, Sangeetha S. Shetty, Yasutomo Masugata, Yasuhito Koyama*
  • Organizer: The 5th Toyama-Basel Joint Symposium on Pharmaceutical Research and Drug Development
  • Int'l Joint Research
• [Presentation] Surface Saccharification and Thermo-Responsive Behaviors of (1→2)-Glucopyranan (2018)
  • Author(s): Abu Bin Ihsan, Sangeetha S. Shetty, Yasutomo Masugata, Yasuhito Koyama*
  • Organizer: 平成30年度有機合成化学北陸セミナー
• [Presentation] Molecular Design and Synthesis for Tuning Thermo-Response of Biopolymers (2018)
  • Author(s): Abu Bin Ihsan, Yasuhito Koyama*
  • Organizer: INTERNATIONAL CONGRESS ON PURE & APPLIED CHEMISTRY (ICPAC Langkawi) 2018
  • Int'l Joint Research / Invited
• [Presentation] Thermally Tunable Nature-Mimetic Polypeptides from N-Protected Alternating Peptoids Towards Tough and Strong Adhesive Materials (2018)
  • Author(s): Abu Bin Ihsan, Yasuhito Koyama*
  • Organizer: 第67回高分子学会北陸支部研究発表会
• [Presentation] 環状サルファイトの開環重合を利用した(1→2)-グルコピラナン類の合成と特性 (2018)
  • Author(s): 小山靖人
  • Organizer: 福井マテリアル＆テクノロジー研究会 秋季事例発表・技術講演会
  • Invited
• [Presentation] 1,2-グリコシド型ポリマー配糖体のワンポット合成とフォルダマー特性 (2017)
  • Author(s): 小山靖人、Sangeetha S. Shetty
  • Organizer: 創薬懇話会2017 in 加賀
• [Presentation] Direct Grafting Reactions of 1,2-Glucopyranan Skeleton as a Fully Aliphatic Helical Foldamer (2017)
  • Author(s): Yasuhito Koyama, Sangeetha S. Shetty
  • Organizer: Chirality2017
• [Presentation] 環状サルファイトの開環重合による1,2-グリコシド型ポリマー配糖体の合成 (2017)
  • Author(s): 小山靖人
  • Organizer: 2017年度セルロース学会西部支部セミナー
  • Invited
• [Book] バイオ3Dプリント関連技術の開発と応用 (2019)
  • Author(s): 小山靖人, アブ ビン イヘサン
  • Total Pages: 269
  • Publisher: 株式会社シーエムシー出版
  • ISBN: 9784781314327
• [Book] Click Polymerization (2018)
  • Author(s): Toshikazu Takata, Yasuhito Koyama, Hiromitsu Sogawa
  • Total Pages: 248
  • Publisher: RSC Publishing
  • ISBN: 9781782627166
• [Remarks] 研究室のwebページ
  • URL: https://www.pu-toyama.ac.jp/PH/koyama/
• [Remarks] 研究室のweb cite
  • URL: https://www.pu-toyama.ac.jp/PH/koyama/
• [Remarks] 研究室のweb cite
  • URL: http://www.pu-toyama.ac.jp/PH/koyama/