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Enzymatic Synthesis of Chitin/Chitosan Stereoisomers as Candidates for Functional Polymeric Materials

Research Project

Project/Area Number 25620177
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Polymer/Textile materials
Research InstitutionKagoshima University

Principal Investigator

KADOKAWA Jun-ichi  鹿児島大学, 理工学域工学系, 教授 (30241722)

Co-Investigator(Kenkyū-buntansha) YAMAMOTO KAZUYA  鹿児島大学, 理工学域工学系, 准教授 (40347084)
Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2015: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2014: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2013: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywordsキチン/キトサン / 酵素触媒重合 / 立体異性体 / ホスホリラーゼ / 非天然型 / 酵素反応
Outline of Final Research Achievements

This study performed the synthesis of chitin/chitosan stereoisomers by thermostable phosphorylase-catalyzed enzymatic polymerization. Phosphorylase catalyzes the enzymatic polymerization of α-D-glucose 1-phosphate (Glc-1-P) as a monomer to produce amylose with liberating inorganic phosphate. Because of loose specificity for the recognition of substrates, in this study, the thermostable phosphorylase-catalyzed enzymatic polymerization of α-D-glucosamine 1-phosphate (GlcN-1-P) as an analogue monomer was achieved under the conditions for removal of inorganic phosphate from the reaction media to give a non-natural aminopolysaccaride, that is, a chitosan stereoisomer. The product was further converted into a chitin stereoisomer by N-acetylation. The thermostable phosphorylase-catalyzed enzymatic copolymerization of Glc-1-P and GlcN-1-P as comonomers was also carried out to produce a non-natural glucosaminoglucan.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (32 results)

All 2016 2015 2014 Other

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Acknowledgement Compliant: 3 results) Presentation (28 results) (of which Int'l Joint Research: 3 results,  Invited: 3 results) Book (1 results)

  • [Journal Article] Enzymes as Green Catalysts for Precision Macromolecular Synthesis2016

    • Author(s)
      Shin-ichiro Shoda, Hiroshi Uyama, Jun-ichi Kadokawa, Shunsaku Kimura, Shiro Kobayashi
    • Journal Title

      Chemical Reviews

      Volume: 116 Issue: 4 Pages: 2307-2413

    • DOI

      10.1021/acs.chemrev.5b00472

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of Non-Natural Heteroaminopolysaccharides by alpha-Glucan Phosphorylase-Catalyzed Enzymatic Copolymerization: alpha(1 -> 4)-Linked Glucosaminoglucans2015

    • Author(s)
      Kento Yamashita, Riko Shimohigoshi, Kazuya Yamamoto, Jun-ichi Kadokawa
    • Journal Title

      Biomacromolecules

      Volume: 16 Issue: 12 Pages: 3989-3994

    • DOI

      10.1021/acs.biomac.5b01332

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of chitin and chitosan stereoisomers by thermostable α-glucan phosphorylase-catalyzed enzymatic polymerization of α-D-glucosamine 1-phosphate2015

    • Author(s)
      Jun-ichi Kadokawa, Riko Shimohigoshi, Kento Yamashita, Kazuya Yamamoto
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 13 Issue: 14 Pages: 4336-4343

    • DOI

      10.1039/c5ob00167f

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] Synthesis of chitin/chitosan stereoisomers by phosphorylase-catalyzed enzymatic polymerization2015

    • Author(s)
      Kento Yamashita, Riko Shimohigoshi, Kazuya Yamamoto, Jun-ichi Kadokawa
    • Organizer
      Pacifichem2015
    • Place of Presentation
      Hawaii Convention Center (Honolulu, USA)
    • Year and Date
      2015-12-17
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of Non-Natural Aminopolysaccharides by Phosphorylase-Catalyzed Enzymatic Polymerization2015

    • Author(s)
      Kento Yamashita, Kazuya Yamamoto, Jun-ichi Kadokawa
    • Organizer
      JTBW2015
    • Place of Presentation
      大阪大学吹田キャンパス(大阪府吹田市)
    • Year and Date
      2015-11-14
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Enzymatic Synthesis of Chitin/Chitosan Stereoisomers by Phosphorylase-catalyzed Polymerization2015

    • Author(s)
      Kento Yamashita, Riko Shimohigoshi, Kazuya Yamamoto, Jun-ichi Kadokawa
    • Organizer
      IUPAC 11th International Conference on Advanced Polymers via Macromolecular Engineering
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2015-10-19
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ホスホリラーゼ酵素触媒重合による両性ブロック多糖の合成2015

    • Author(s)
      高田祐成、山元和哉、門川淳一
    • Organizer
      第64回高分子討論会
    • Place of Presentation
      東北大学川内キャンパス(宮城県仙台市)
    • Year and Date
      2015-09-16
    • Related Report
      2015 Annual Research Report
  • [Presentation] ホスホリラーゼ酵素触媒重合による非天然型アミノ多糖の合成2015

    • Author(s)
      山下健人、山元和哉、門川淳一
    • Organizer
      第64回高分子討論会
    • Place of Presentation
      東北大学川内キャンパス(宮城県仙台市)
    • Year and Date
      2015-09-15
    • Related Report
      2015 Annual Research Report
  • [Presentation] ホスホリラーゼ酵素触媒共重合によるグルコサミノグルコグリカンの合成2015

    • Author(s)
      山下健人、下吹越理子、山元和哉、門川淳一
    • Organizer
      第52回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場(福岡県北九州市)
    • Year and Date
      2015-06-27
    • Related Report
      2015 Annual Research Report
  • [Presentation] 両性ブロック多糖の化学‐酵素合成2015

    • Author(s)
      高田祐成、山元和哉、門川淳一
    • Organizer
      第64回高分子学会年次大会
    • Place of Presentation
      札幌コンベンションセンター(北海道札幌市)
    • Year and Date
      2015-05-29
    • Related Report
      2015 Annual Research Report
  • [Presentation] ホスホリラーゼ酵素触媒重合によるキトサン立体異性体多糖の合成2015

    • Author(s)
      山下健人、下吹越理子、山元和哉、門川淳一
    • Organizer
      第64回高分子学会年次大会
    • Place of Presentation
      札幌コンベンションセンター(北海道札幌市)
    • Year and Date
      2015-05-29
    • Related Report
      2015 Annual Research Report
  • [Presentation] ホスホリラーゼ酵素触媒共重合による非天然型アミノ多糖の合成2015

    • Author(s)
      山下健人、山元和哉、門川淳一
    • Organizer
      第64回高分子学会年次大会
    • Place of Presentation
      札幌コンベンションセンター(北海道札幌市)
    • Year and Date
      2015-05-29
    • Related Report
      2015 Annual Research Report
  • [Presentation] 酵素触媒重合によるキトサン立体異性体多糖の合成2015

    • Author(s)
      山下 健人、下吹越 理子、山元 和哉、門川 淳一
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学(船橋市)
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] アナログ基質を用いた酵素反応による新規糖鎖の精密合成2015

    • Author(s)
      門川淳一
    • Organizer
      第25回繊維学会西部支部セミナー
    • Place of Presentation
      琉球大学(沖縄県中頭郡西原町)
    • Year and Date
      2015-02-06
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] Enzymatic Synthesis of Non-natural Aminopolysaccharide by Thermostable Phosphorylase Catalysis2014

    • Author(s)
      Riko Shimohigoshi, Kazuya Yamamoto and Jun-ichi Kadokawa
    • Organizer
      The 10th SPSJ International Polymer Conference (IPC 2014)
    • Place of Presentation
      つくば国際会議場(つくば市)
    • Year and Date
      2014-12-03
    • Related Report
      2014 Research-status Report
  • [Presentation] Enzymatic Synthesis of Novel Functional Oligo- and Polysaccharides by Phosphorylase Catalysis2014

    • Author(s)
      Jun-ichi Kadokawa
    • Organizer
      World Gene Convention-2014
    • Place of Presentation
      海口(中国)
    • Year and Date
      2014-11-14
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] 酵素で創る非天然型多糖・オリゴ糖 ~ホスホリラーゼのアナログ基質を用いた新規糖鎖の酵素合成~2014

    • Author(s)
      門川淳一
    • Organizer
      第8回多糖の未来フォーラムシンポジウム
    • Place of Presentation
      九州大学(福岡市)
    • Year and Date
      2014-11-06
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] 耐熱性ホスホリラーゼによる非天然型アミノ多糖の酵素合成2014

    • Author(s)
      下吹越理子、山元和哉、門川淳一
    • Organizer
      第4回CSJ化学フェスタ
    • Place of Presentation
      タワーホール船堀(東京都)
    • Year and Date
      2014-10-15
    • Related Report
      2014 Research-status Report
  • [Presentation] Thermostable phosphorylase-catalyzed enzymatic synthesis of chitosan stereoisomer2014

    • Author(s)
      Kento Yamashita, Riko Shimohigoshi, Kazuya Yamamoto, Jun-ichi Kadokawa
    • Organizer
      TJBW-2014
    • Place of Presentation
      台南(台湾)
    • Year and Date
      2014-10-13
    • Related Report
      2014 Research-status Report
  • [Presentation] 耐熱性ホスホリラーゼ触媒グルコサミニル化反応によるα-グルコサミン鎖の合成と反応解析2014

    • Author(s)
      山下健人、下吹越理子、山元和哉、門川淳一
    • Organizer
      第63回高分子討論会
    • Place of Presentation
      長崎大学(長崎市)
    • Year and Date
      2014-09-24
    • Related Report
      2014 Research-status Report
  • [Presentation] Enzymatic synthesis of chitin/chitosan stereoisomers by thermostable phosphorylase catalysis2014

    • Author(s)
      Jun-ichi Kadokawa, Riko Shimohigoshi, Kazuya Yamamoto
    • Organizer
      ACS 248th National Meeting
    • Place of Presentation
      サンフランシスコ(アメリカ合衆国)
    • Year and Date
      2014-08-10
    • Related Report
      2014 Research-status Report
  • [Presentation] 耐熱性ホスホリラーゼによるキトサン立体異性体糖鎖の酵素合成2014

    • Author(s)
      山下健人、下吹越理子、畑中大輔、山元和哉、門川淳一
    • Organizer
      セルロース学会第21回年次大会
    • Place of Presentation
      鹿児島大学(鹿児島市)
    • Year and Date
      2014-07-17
    • Related Report
      2014 Research-status Report
  • [Presentation] Enzymatic Synthesis of Non-natural α-Glucosamine Chains by Thermostable Phosphorylase Catalysis2014

    • Author(s)
      Riko Shimohigoshi, Kazuya Yamamoto, Jun-ichi Kadokawa
    • Organizer
      2014 IUPAC World Polymer Congress (MACRO 2014)
    • Place of Presentation
      チェンマイ(タイ)
    • Year and Date
      2014-07-10
    • Related Report
      2014 Research-status Report
  • [Presentation] 耐熱性ホスホリラーゼによるα‐グルコサミン鎖の酵素合成2014

    • Author(s)
      下吹越理子、山元和哉、門川淳一
    • Organizer
      第51回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場(北九州市)
    • Year and Date
      2014-06-28
    • Related Report
      2014 Research-status Report
  • [Presentation] 耐熱性ホスホリラーゼによる非天然型アミノ糖鎖の酵素合成2014

    • Author(s)
      山下健人、畑中大輔、下吹越理子、山元和哉、門川淳一
    • Organizer
      平成26年度繊維学会年次大会
    • Place of Presentation
      タワーホール船堀(東京都)
    • Year and Date
      2014-06-12
    • Related Report
      2014 Research-status Report
  • [Presentation] 耐熱性ホスホリラーゼによる連続的グルコサミニル化反応を利用したα‐グルコサミン鎖の合成2014

    • Author(s)
      下吹越理子、山元和哉、門川淳一
    • Organizer
      第63回高分子学会年次大会
    • Place of Presentation
      名古屋国際会議場(名古屋市)
    • Year and Date
      2014-05-28
    • Related Report
      2014 Research-status Report
  • [Presentation] 耐熱性ホスホリラーゼによる酵素反応を利用したキチン/キトサン立体異性体糖鎖の合成

    • Author(s)
      門川淳一・竹本康高・山元和哉
    • Organizer
      第62回高分子学会年次大会
    • Place of Presentation
      京都国際会館(京都市)
    • Related Report
      2013 Research-status Report
  • [Presentation] 耐熱性ホスホリラーゼによるキトサン立体異性体オリゴ糖の酵素合成

    • Author(s)
      下吹越理子・竹本康高・山元和哉・門川淳一
    • Organizer
      第50回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場(北九州市)
    • Related Report
      2013 Research-status Report
  • [Presentation] Phosphorylase-catalyzed enzymatic glycosylations using analogue substrates toward synthesis of cnitin/chitosan stereoisomers

    • Author(s)
      Jun-ichi Kadokawa
    • Organizer
      15th Asian Chemical Congress
    • Place of Presentation
      Resorts World Sentosa Convention Centre(Singapore)
    • Related Report
      2013 Research-status Report
  • [Presentation] Enzymatic synthesis of chitin/chitosan stereoisomers

    • Author(s)
      Jun-ichi Kadokawa
    • Organizer
      Japan-Taiwan Bilateral Workshop 2013
    • Place of Presentation
      鹿児島大学(鹿児島市)
    • Related Report
      2013 Research-status Report
  • [Presentation] 耐熱性ホスホリラーゼを用いるα-グルコサミン鎖の酵素合成

    • Author(s)
      下吹越理子・山元和哉・門川淳一
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学東山キャンパス(名古屋市)
    • Related Report
      2013 Research-status Report
  • [Book] Green Polymer Chemistry: Biobased Materials and Biocatalysis, ACS Symposium Series 11922015

    • Author(s)
      Jun-ichi Kadokawa
    • Total Pages
      13
    • Publisher
      American Chemical Society
    • Related Report
      2015 Annual Research Report

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Published: 2014-07-25   Modified: 2019-07-29  

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