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Synthetic study on the mycobacterial cell wall glycoconjugate

Research Project

Project/Area Number 26350966
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Biomolecular chemistry
Research InstitutionInstitute of Physical and Chemical Research

Principal Investigator

ISHIWATA AKIHIRO  国立研究開発法人理化学研究所, 伊藤細胞制御化学研究室, 専任研究員 (70342748)

Project Period (FY) 2014-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywordsグリコシル化 / 立体選択的合成 / 複合糖質 / オリゴ糖 / 結核菌細胞壁 / 収斂的合成 / 多糖
Outline of Final Research Achievements

As part of chemical study on glycoconjugate in the cell wall component of mycobacteria, oligoarabinofuranosides has been synthesized in order to use as the probe with fragment structure of the arabinan which is the outmost glycan of cell wall glycoconjugate.
For the analysis of the novel hydrolases of arabinan, label-free ESI Mass analysis of the products degraded by the enzyme has been carried out. Furthermore, for the development of general methodology toward synthesis of the 1.2-cis glycosidic linkages, intramolecular aglycon delivery (IAD) has been examined. The syntheses and structural analysis of oligosaccharides found in hydrophilic motif of HRGP, various plant polysaccharides and oligosaccharide-modified structure of marine toxin have been demonstrated. On the other hand, based on the study on glycan modification process of bacterial N-linked glycoprotein by chemical and enzymatic techniques, substrate specificity of the key oligosaccharyl transferase could be suggested.

Report

(5 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (51 results)

All 2018 2017 2016 2015 2014

All Journal Article (5 results) (of which Open Access: 1 results,  Peer Reviewed: 2 results,  Acknowledgement Compliant: 1 results) Presentation (44 results) (of which Int'l Joint Research: 10 results,  Invited: 5 results) Book (2 results)

  • [Journal Article] 緑膿菌転写調節因子AmpR作用領域のムロペプチドとのX線構造2017

    • Author(s)
      石渡明弘、伊藤幸成
    • Journal Title

      Chemical Biology

      Volume: 10 Pages: 16-16

    • Related Report
      2017 Annual Research Report
  • [Journal Article] Study on N-glycosylation of synthetic substrates by PglB oligosaccharyltransferase from Gram-negative bacterium Campylobacter jejuni2015

    • Author(s)
      Ishiwata, A.;* Taguchi, Y.; Lee, Y. J.; Watanabe, T.; Koda, D.;* Ito, Y.*
    • Journal Title

      Proceeding for Symposium on the chemistry of natural products

      Volume: 57 Pages: 603-608

    • NAID

      130007491912

    • Related Report
      2015 Research-status Report
    • Open Access
  • [Journal Article] N-Glycosylation with Synthetic Undecaprenyl Pyrophosphate-Linked Oligosaccharide to Oligopeptides by PglB Oligosaccharyltransferase from Campylobacter jejuni2015

    • Author(s)
      Ishiwata A, Taguchi Y, Lee YJ, Watanabe T, Kohda D, Ito Y.
    • Journal Title

      Chembiochem

      Volume: 16 Issue: 5 Pages: 731-737

    • DOI

      10.1002/cbic.201402658

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of Highly Glycosylated Hydrophilic Motif of Extensins2014

    • Author(s)
      Ishiwata, A.; Kaeothip, S.; Takeda, Y.; Ito, Y.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 53 Issue: 37 Pages: 9812-9816

    • DOI

      10.1002/anie.201404904

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthetic study and structural analysis of one of hydrophilic motifs of hydroxyproline-rich glycoprotein extensin2014

    • Author(s)
      Ishiwata, A.; Kaeothip, S.; Takeda, Y.; Ito, Y.
    • Journal Title

      Proceeding for Symposium on the chemistry of natural products

      Volume: 56 Pages: 37-42

    • NAID

      130007399463

    • Related Report
      2014 Research-status Report
  • [Presentation] 1,2-cis O-グリコシドの立体選択的構築へのアプローチ2018

    • Author(s)
      ○ 石渡明弘
    • Organizer
      第一回糖化学フォーラム
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] N-(L-アラビノフラノシル) ハロアセトアミド両異性体の立体選択的合成2018

    • Author(s)
      ○ 成田覚, 石渡明弘, 伊藤幸成
    • Organizer
      日本農芸化学会2018年度大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 結核菌アラビナン分解酵素の機能解析に向けた オリゴアラビノフラノシド誘導体の合成研究2018

    • Author(s)
      ○ 石渡明弘, 伊藤幸成
    • Organizer
      日本農芸化学会2018年度大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 渦鞭毛藻由来 -1,5 結合した-L-アラビノフラノシド三糖構造の構築と構造解析2018

    • Author(s)
      ○ 石渡明弘, 伊藤幸成
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Synthetic studies on L-arabinofuranosylated probes for bifidobacterial -L-arabinofuranosidase2018

    • Author(s)
      ○ Ishiwata, A.; Narita, S.; Kimura, K.; Fushinobu S.; Fujita K.; Ito, Y.
    • Organizer
      International Symposium on ER stress, glycosylation, homeostasis and diseases
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Stereoselective synthesis of bacterial and plant glycoconjugates as substrate for glycan-related enzymes2017

    • Author(s)
      Ishiwata, A.
    • Organizer
      3rd RIKEN-Academia Sinica Joint conference: Focus on Chemistry and Chemical Biology on Chemical Biology
    • Place of Presentation
      Wako, Japan
    • Year and Date
      2017-03-30
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 1,5-結合したβ-L-アラビノフラノシドを有するオリゴアラビノフラノシドの合成と構造解析2017

    • Author(s)
      丸山瞬, 伊藤佑, 藤田清貴, 石渡明弘, 伊藤幸成, 荒川孝俊, 伏信進矢
    • Organizer
      日本農芸化学会2017年度大会
    • Place of Presentation
      京都女子大、京都
    • Year and Date
      2017-03-19
    • Related Report
      2016 Research-status Report
  • [Presentation] B. longum JCM1217由来GH127 β-l-アラビノフラノシダーゼ(HypBA1)の機能構造解析2017

    • Author(s)
      丸山瞬, 伊藤佑, 藤田清貴, 石渡明弘, 伊藤幸成, 荒川孝俊, 伏信進矢
    • Organizer
      日本農芸化学会2017年度大会
    • Place of Presentation
      京都女子大、京都
    • Year and Date
      2017-03-18
    • Related Report
      2016 Research-status Report
  • [Presentation] β-L-アラビノフラノシドを有する植物由来オリゴアラビノフラノシドの合成と構造解析2017

    • Author(s)
      石渡明弘, 伊藤幸成
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応義塾大学、横浜
    • Year and Date
      2017-03-17
    • Related Report
      2016 Research-status Report
  • [Presentation] Studies on β-L-arabinofuranosylated oligosaccharides and glycoconjugates from plant2017

    • Author(s)
      ○ Ishiwata, A.; Fushinobu S.; Fujita K.; Ito, Y.
    • Organizer
      EUROCARBO 2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 渦鞭毛藻由来β-アラビノフラノシド構造の立体選択的構築と構造解析2017

    • Author(s)
      ○ 石渡明弘, 伊藤幸成
    • Organizer
      第36回日本糖質学会年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] L-アラビノフラノシルアジド誘導体を経由するL-アラビノフラノース誘導体プローブの立体選択的合成検討2017

    • Author(s)
      ○成田覚, 石渡明弘, 伊藤幸成
    • Organizer
      第36回日本糖質学会年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Bifidobacterium longum 由来の -L-アラビノフラノシダーゼの機能解析2017

    • Author(s)
      ○藤田清貴, 石渡明弘, 伊藤幸成, 若尾雅広, 隅田泰生, 北原兼文
    • Organizer
      第36回日本糖質学会年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Aureobacterium sp. M2 由来 Endo-D-arabinase の基質特異性の解析2017

    • Author(s)
      ○澤井未視, 下川倫子, 石渡明弘, 伊藤幸成, 若尾雅広, 隅田泰生, 北原兼文, 藤田清貴
    • Organizer
      日本応用糖質科学会平成29年度大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] L-アラビノフラノシルアミン誘導体の立体選択的合成検討2017

    • Author(s)
      ○成田覚, 木村謙太, 石渡明弘, 伊藤幸成
    • Organizer
      日本応用糖質科学会平成29年度大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 渦鞭毛藻由来海産毒の糖修飾構造オリゴβ-L-アラビノフラノシドの立体選択的構築と構造解析2017

    • Author(s)
      ○石渡明弘, 伊藤幸成
    • Organizer
      日本応用糖質科学会平成29年度大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Studies on plant -L-arabinofuranosylated oligosaccharides and glycoconjugates2017

    • Author(s)
      ○ Ishiwata, A.; Fujita K.; Fushinobu S.; Ito, Y.
    • Organizer
      International Symposium “Systems Glycobiology and Beyond”
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Stereoselective and Divergent Synthesis of Anomeric Isomers of Triglucosides Using a Single Donor.2017

    • Author(s)
      ○ Ding F. Q.; Ishiwata A.; Ito Y.
    • Organizer
      International Symposium “Systems Glycobiology and Beyond”
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] L-アラビノフラノシルアジドの合成とL-アラビノフラノシルアミン誘導体の立体選択的合成検討2017

    • Author(s)
      ○ 成田覚, 木村謙太, 石渡明弘, 藤田清貴, 伊藤幸成
    • Organizer
      東北糖鎖研究会・東京糖鎖研究会合同シンンポジウム, 第11回東北糖鎖研究会・GlycoTOKYO2017
    • Related Report
      2017 Annual Research Report
  • [Presentation] 細菌や植物由来の複合糖質糖鎖の合成と応用2017

    • Author(s)
      ○ 石渡明弘
    • Organizer
      東北糖鎖研究会・東京糖鎖研究会合同シンンポジウム, 第11回東北糖鎖研究会・GlycoTOKYO2017
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 2-O-(ortho-tosylamidobenzyl) Glucosyl Donor for Stereoselective Preparation of All Possible Anomeric Isomers of D-Glc-(1→2)-D-Glc-(1→6)-D-Glc2017

    • Author(s)
      ○ Ding F.Q.; Ishiwata A.; Ito Y.
    • Organizer
      東北糖鎖研究会・東京糖鎖研究会合同シンンポジウム, 第11回東北糖鎖研究会・GlycoTOKYO2017
    • Related Report
      2017 Annual Research Report
  • [Presentation] Lipoarabinomannan に作用する新規 D-アラビナン分解酵素2017

    • Author(s)
      ○藤田清貴, 石渡明弘, 伊藤幸成, 若尾雅広, 隅田泰生, 北原兼文
    • Organizer
      第2回抗酸菌研究会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Synthesis and structural analysis of glycoconjugates as the substrate for glycan-related enzymes2017

    • Author(s)
      ○ Ishiwata, A.
    • Organizer
      Japan-China joint symposium on natural products to promote the use of high magnetic field and high sensitivity NMR 2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Xanthomonas 属細菌由来 -L-アラビノフラノシダーゼの結晶構造2017

    • Author(s)
      ○澤野 孝太, 丸山 瞬, 石渡 明弘, 伊藤 幸成, 藤田 清貴, 伏信 進矢
    • Organizer
      2017年日本生化学会・日本分子生物学会合同大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Synthesis and structural analysis of plant -L-arabinofuranosylated oligoarabinofuranosides2017

    • Author(s)
      ○ Ishiwata A.; Ito Y.
    • Organizer
      9th Asian Community of Glycoscience and Glycotechology Conference
    • Related Report
      2017 Annual Research Report
  • [Presentation] Stereodivergent O-Glycosylation by a “Single Donor”: Preparation of Anomeric Isomers of Triglucosides.2017

    • Author(s)
      ○ Ding F. Q.; Ishiwata A.; Ito Y.
    • Organizer
      9th Asian Community of Glycoscience and Glycotechology Conference
    • Related Report
      2017 Annual Research Report
  • [Presentation] 植物由来 β-L-アラビノフラノシド構造を有するオリゴ糖及び誘導体の合成検討2016

    • Author(s)
      石渡明弘, 成田覚, 木村謙太, 伊藤幸成
    • Organizer
      GlycoTOKYO2016シンポジウム
    • Place of Presentation
      東京工業大、東京
    • Year and Date
      2016-11-19
    • Related Report
      2016 Research-status Report
  • [Presentation] Stereoselective synthesis of 1,2-cis-b-arabinofuranosylated oligosaccharides and glycoconjugates from plant2016

    • Author(s)
      Ishiwata, A.; Ito, Y.
    • Organizer
      8th Asian Community of Glycobiology and Glycoscience 2016
    • Place of Presentation
      Wuxi, Jiangsu, China
    • Year and Date
      2016-10-14
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] β-1,3-結合に作用する β-L-アラビノフラノシダーゼの機能解析2016

    • Author(s)
      藤田清貴, 角町華子, 石渡明弘, 伊藤幸成, 北原兼文
    • Organizer
      日本応用糖質科学会平成28年度大会(65回)
    • Place of Presentation
      福山大学宮地茂記念館, 福山
    • Year and Date
      2016-09-14
    • Related Report
      2016 Research-status Report
  • [Presentation] 植物由来 β-L-アラビノフラノシド含有糖鎖の合成2016

    • Author(s)
      石渡明弘, 伊藤幸成
    • Organizer
      日本応用糖質科学会平成28年度大会(65回)
    • Place of Presentation
      福山大学宮地茂記念館, 福山
    • Year and Date
      2016-09-14
    • Related Report
      2016 Research-status Report
  • [Presentation] 植物由来 β-L-アラビノフラノシド構造の立体選択的構築2016

    • Author(s)
      石渡明弘, 伊藤幸成
    • Organizer
      第35回日本糖質学会年会
    • Place of Presentation
      高知市文化プラザ かるぽーと、高知
    • Year and Date
      2016-09-03
    • Related Report
      2016 Research-status Report
  • [Presentation] Stereoselective synthesis of oligo-L-arabinofuranosides, its derivatives and L-arabinofuranosylated probes for beta-L-arabinofuranosidases2016

    • Author(s)
      Ishiwata, A.; Kaeothip, S.; Ito, Y.
    • Organizer
      28th International Carbohydrate Symposium,
    • Place of Presentation
      New Orleans Louisiana, USA
    • Year and Date
      2016-07-20
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Characterization of novel -L-arabinofuranosidases acting on HRGPs2016

    • Author(s)
      Fujita, K.; Tsunomachi, H.; Ishiwata, A.; Ito, Y. Kitahara, K.,
    • Organizer
      10th Georgia Glycoscience Symposium / Plant Polysaccharide Workshop 2016
    • Place of Presentation
      Athens, Georgia, USA
    • Year and Date
      2016-07-14
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] 遠隔位からの分子内アグリコン転移反応によるシスグリコシル化の検討2016

    • Author(s)
      ○ 石渡明弘, 伊藤幸成
    • Organizer
      日本農芸化学会2016年度大会
    • Place of Presentation
      札幌コンベンションセンター、札幌、北海道
    • Year and Date
      2016-03-27
    • Related Report
      2015 Research-status Report
  • [Presentation] 遠隔位からの分子内アグリコン転移反応の検討2016

    • Author(s)
      ○ 石渡明弘, 伊藤幸成,
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学、京田辺、京都
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] Study on stereoselective cis-glycosylations through NAP ether-mediated intramolecular aglycon delivery2015

    • Author(s)
      ○ Ishiwata, A.; Ito, Y.
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      Hawaii, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Aureobacterium sp. M2由来のエンド-D-アラビナーゼの精製と諸性質の解析2015

    • Author(s)
      ○ 澤井未視、下川倫子、石渡明弘、伊藤幸成、若尾雅広、隅田泰生、北原兼文、藤田清貴
    • Organizer
      第67回日本生物工学会大会
    • Place of Presentation
      城山観光ホテル、鹿児島、鹿児島
    • Year and Date
      2015-10-26
    • Related Report
      2015 Research-status Report
  • [Presentation] グラム陰性菌 Campylobacter jejuni 由来 PglB オリゴ糖転移酵素による合成基質を用いた N-グリコシル化に関する研究2015

    • Author(s)
      ○ 石渡明弘, 田口裕也, Yong Joo Lee, 渡邉泰輔, 神田大輔, 伊藤幸成
    • Organizer
      第57回天然有機化合物討論会
    • Place of Presentation
      神奈川県民ホール、横浜、神奈川
    • Year and Date
      2015-10-15
    • Related Report
      2015 Research-status Report
  • [Presentation] βーアラビノオリゴ糖鎖に作用するβ-L-アラビノフラノシダーゼの機能解析2015

    • Author(s)
      ○ 藤田清貴, 亀山恭平, 下川倫子, 伏信進矢, 石渡明弘, Sophon Kaeothip, 伊藤幸成, 北原兼文
    • Organizer
      第34回日本糖質学会年会
    • Place of Presentation
      東京大学、文京、東京
    • Year and Date
      2015-07-29
    • Related Report
      2015 Research-status Report
  • [Presentation] NAPエーテルを介した分子内アグリコン転移反応を利用した選択的cis-グリコシル化の検討2015

    • Author(s)
      ○ 石渡明弘, 伊藤幸成
    • Organizer
      第34回日本糖質学会年会
    • Place of Presentation
      東京大学、文京、東京
    • Year and Date
      2015-07-29
    • Related Report
      2015 Research-status Report
  • [Presentation] 植物細胞壁成分エクステンシンの親水性モチーフの合成と構造解析2015

    • Author(s)
      ○石渡明弘, Sophon Kaeothip, 武田陽一, 伊藤幸成,
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学(埼玉県船橋市)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthetic study and structural analysis of highly glycosylated hydrophilic motif of plant extensins2014

    • Author(s)
      ○Ishiwata, A.; Kaeothip, S.; Takeda, Y.; Ito, Y.
    • Organizer
      Joint Meeting of the Society for Glycobiology (SFG) and the Japanese Society of Carbohydrate Research (JSCR)
    • Place of Presentation
      Hilton Hawaiian Village (Honolulu, USA)
    • Year and Date
      2014-11-16 – 2014-11-19
    • Related Report
      2014 Research-status Report
  • [Presentation] ヒドロキシプロリンリッチ糖タンパク質 extensin の親水性モチーフの合成と構造解析2014

    • Author(s)
      ○石渡明弘, Sophon Kaeothip, 武田陽一, 伊藤幸成
    • Organizer
      第56回天然有機化合物討論会
    • Place of Presentation
      高知県立県民文化ホール(高知県高知市)
    • Year and Date
      2014-10-15 – 2014-10-17
    • Related Report
      2014 Research-status Report
  • [Presentation] 植物細胞外マトリックス成分 extensin の親水性モチーフの合成と構造解析2014

    • Author(s)
      ○石渡明弘, Sophon Kaeothip, 武田陽一, 伊藤幸成
    • Organizer
      第33回日本糖質学会年会
    • Place of Presentation
      名古屋大学 (愛知県名古屋市)
    • Year and Date
      2014-08-10 – 2014-08-12
    • Related Report
      2014 Research-status Report
  • [Book] "Intramolecular Aglycon Derivery" In Selective Glycosylations - Synthetic Methods and Catalysts2017

    • Author(s)
      Ishiwata, A.; Ito, Y. (Bennett, C. S. Ed.)
    • Publisher
      Wiley, Weinheim
    • Related Report
      2016 Research-status Report
  • [Book] "Synthesis of Bacterial Cell Envelope Components" In Glycochemical Synthesis: Strategies and Applications2016

    • Author(s)
      Ishiwata, A.; Ito, Y. (Hung, S.-C.; Zulueta, M. M. L. Eds.)
    • Publisher
      Wiley, Weinheim
    • Related Report
      2016 Research-status Report

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Published: 2014-04-04   Modified: 2019-03-29  

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