Approach toward chemical synthesis of highly branched glycans of glycoconjugate

• Project/Area Number: 22510243
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Living organism molecular science
• Research Institution: The Institute of Physical and Chemical Research
• Principal Investigator: ISHIWATA Akihiro 独立行政法人理化学研究所, 伊藤細胞制御化学研究室, 専任研究員 (70342748)
• Project Period (FY): 2010 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000); Fiscal Year 2012: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2011: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2010: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
• Keywords: 糖鎖合成 / オリゴ糖 / 立体選択的合成 / グリコシル化 / 収斂的合成 / 複合糖質糖鎖 / 多分岐糖鎖 / グリコシル化反応

Research Abstract

Long-distance intramolecular aglycon delivery (IAD) was conducted to construct 1.2-cis glycosidic linkages whose stereoselective synthesis is one of the most difficult. The convergent strategy toward tetrabranched docosa- and hentriaconta-saccharide arabinan from Mycobacterial arabinan and the strategy for construction of highly branched structure have been studied. IAD method has been improved to achieve the syntheses of core structure of N-glycan and antifreeze glycan fragment from Upis ceramboides. The concentration effect on various factors of accelerated O-glycosylation when the reaction solvent was frozen has been studied.

Research Products

• [Journal Article] Biotechnological Approaches toward the Synthesis of Eukaryotic <i>N</i>-Linked Glycoprotein (2012)
  • Author(s): Ishiwata, A.
  • Journal Title: Trends in Glycoscience and Glycotechnology Volume: 24 Issue: 139 Pages: 225-227
  • DOI: 10.4052/tigg.24.225
  • NAID: 10031146674
  • ISSN: 0915-7352, 1883-2113
  • Peer Reviewed
• [Journal Article] Accelerated <i>O</i>-Glycosylation under Frozen Conditions and Its Application to the Synthesis of Complex Glycans (2012)
  • Author(s): Ishiwata, A.; Sakurai, A.; Ito, Y.
  • Journal Title: Trends in Glycoscience and Glycotechnology Volume: 24 Issue: 138 Pages: 179-189
  • DOI: 10.4052/tigg.24.179
  • NAID: 10031146669
  • ISSN: 0915-7352, 1883-2113
  • Peer Reviewed
• [Journal Article] Intramolecular Aglycon Delivery and Its Application to Stereoselective Synthesis of Glycans (2012)
  • Author(s): 石渡明弘, 伊藤幸成
  • Journal Title: Journal of Synthetic Organic Chemistry, Japan Volume: 70 Issue: 4 Pages: 382-394
  • DOI: 10.5059/yukigoseikyokaishi.70.382
  • NAID: 10030576919
  • ISSN: 0037-9980, 1883-6526
  • Peer Reviewed
• [Journal Article] Synthetic study and structural analysis of the antifreeze agent xylomannan from Upis ceramboides (2011)
  • Author(s): Ishiwata, A.; Sakurai, A.; Nishimiya, Y.; Tsuda, S.; Ito, Y.
  • Journal Title: J. Am. Chem. Soc Volume: 133 Issue: 48 Pages: 19524-19535
  • DOI: 10.1021/ja208528c
  • Peer Reviewed
• [Journal Article] Drug-Resistant Tuberculosis and Inhibition of Biosynthetic Enzymes for Polysaccharides in Mycobacterial Cell Wall (2011)
  • Author(s): Ishiwata, A.
  • Journal Title: Trends in Glycoscience and Glycotechnology Volume: 23 Issue: 130 Pages: 106-107
  • DOI: 10.4052/tigg.23.106
  • NAID: 10029582816
  • ISSN: 0915-7352, 1883-2113
  • Peer Reviewed
• [Journal Article] Synthesis of docosasaccharide arabinan motif of mycobacterial cell wall (2011)
  • Author(s): Ishiwata, A.; Ito, Y.
  • Journal Title: J. Am. Chem. Soc Volume: 133 Issue: 7 Pages: 2275-2291
  • DOI: 10.1021/ja109932t
  • Peer Reviewed
• [Journal Article] Synthesis of docosasaccharide arabinan motif of mycobacterial cell wall (2011)
  • Author(s): Ishiwata, A.; Ito, Y.
  • Journal Title: J.Am.Chem.Soc. Volume: 133 Pages: 2275-2291
  • Peer Reviewed
• [Journal Article] Effects of frozen conditions on stereoselectivity and velocity of O-glycosylation reactions (2010)
  • Author(s): Ishiwata, A.; Sakurai, A.; Durr, K.; Ito, Y.
  • Journal Title: Bioorg. Med. Chem Volume: 18 Issue: 11 Pages: 3678-3695
  • DOI: 10.1016/j.bmc.2010.04.013
  • Peer Reviewed
• [Journal Article] Effects of frozen conditions on stereoselectivity and velocity of O-glycosylation reactions (2010)
  • Author(s): Ishiwata, A.; Sakurai, A.; Durr, K.; Ito, Y.
  • Journal Title: Bioorg.Med.Chem. Volume: 18 Pages: 3678-3695
  • Peer Reviewed
• [Journal Article] Recent advances in stereoselective glycosylation through intramolecular aglycon delivery (2010)
  • Author(s): Ishiwata, A.; Lee, Y.J.; Ito, Y.
  • Journal Title: Org.Biomol.Chem. Volume: 8 Pages: 3596-3608
  • Peer Reviewed
• [Presentation] 分子内アグリコン転移反応を利用した、β-L-アラビノフラノシド誘導体の合成研究 (2013)
  • Author(s): 石渡明弘, Sophon Kaeothip, 伊藤幸成
  • Organizer: 日本農芸化学会2013年度大会
  • Place of Presentation: 仙台
• [Presentation] 分子内アグリコン転移反応を利用した、マンノースキャッピングされたアラビナン構造の構築検討 (2013)
  • Author(s): 石渡明弘, 伊藤幸成
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 滋賀
• [Presentation] 新規不凍活性物質キシロマンナンの合成研究と構造解 (2012)
  • Author(s): 石渡明弘, 櫻井絢花, 伊藤幸成
  • Organizer: GlycoTOKYO2012シンポジウム
  • Place of Presentation: 東京
  • Year and Date: 2012-11-17
• [Presentation] Stereoselective Constructions of Complex Bacterial Glycans (2012)
  • Author(s): Ishiwata, A.; Ito, Y.
  • Organizer: 4th Asian Communication for Glycobiology and Glycotechnology
  • Place of Presentation: Jeju, Korea(Invited)
• [Presentation] NAPエーテルを介した分子内アグリコン転移反応の応用:1,2-cis グリコシドを含む、キシロマンナンフラグメントの立体選択的構築 (2012)
  • Author(s): 石渡明弘, 櫻井絢花, 伊藤幸成
  • Organizer: 第31回日本糖質学会年会
  • Place of Presentation: 鹿児島
• [Presentation] Application of NAP ether-mediated intramolecular aglycon delivery to stereoselective construction of xylomannan fragment containing 1,2-cis glycosides (2012)
  • Author(s): Ishiwata, A.; Sakurai, A.; Ito, Y.
  • Organizer: 26^<th> International Carbohydrate Symposium
  • Place of Presentation: Madrid, Spain
• [Presentation] 分子内アグリコン転移反応を利用した、Upis ceramboides 由来キシロマンナン不凍多糖の合成研究と構造解析 (2012)
  • Author(s): 石渡明弘, 櫻井絢花, 伊藤幸成
  • Organizer: 日本農芸化学会2012年度大会
  • Place of Presentation: 京都
• [Presentation] 結核菌由来アラビナン4分岐31糖の合成研究 (2012)
  • Author(s): 石渡明弘, 伊藤幸成
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 横浜
• [Presentation] Application of NAP ether-mediated intramolecular aglycon delivery to stereoselective construction of xylomannan fragment containing 1,2-cis glycosides (2012)
  • Author(s): Ishiwata, A.; Sakurai, A.; Ito, Y.
  • Organizer: 26th International Carbohydrate Symposium
  • Place of Presentation: Madrid, Spain
• [Presentation] Stereoselective Constructions of Complex Bacterial Glycans (2012)
  • Author(s): Ishiwata, A.; Ito, Y.
  • Organizer: 4th Asian Communication for Glycobiology and Glycotechnology
  • Place of Presentation: Jeju, Korea
  • Invited
• [Presentation] NAPエーテルを介した分子内アグリコン転移反応の応用：1,2-cis グリコシドを含む、キシロマンナンフラグメントの立体選択的構築 (2012)
  • Author(s): 石渡明弘, 櫻井絢花, 伊藤幸成
  • Organizer: 第31回日本糖質学会年会
  • Place of Presentation: 鹿児島
• [Presentation] 新規不凍活性物質キシロマンナンの合成研究と構造解析 (2012)
  • Author(s): 石渡明弘, 櫻井絢花, 伊藤幸成
  • Organizer: GlycoTOKYO2012シンポジウム
  • Place of Presentation: 東京
• [Presentation] 分子内アグリコン転移反応を利用した、Upis ceramboides由来キシロマンナン不凍多糖の合成研究と構造解析 (2012)
  • Author(s): 石渡明弘, 櫻井絢花, 伊藤幸成
  • Organizer: 日本農芸化学会2012年度大会
  • Place of Presentation: 京都
• [Presentation] 細菌由来複合糖質糖鎖の合成研究 (2011)
  • Author(s): 石渡明弘
  • Organizer: GlycoTOKYO2011シンポジウム,
  • Place of Presentation: 和光(招待講演)
  • Year and Date: 2011-12-09
• [Presentation] 細菌由来複合糖質糖鎖の合成研究 (2011)
  • Author(s): 石渡明弘
  • Organizer: GlycoTOKYO2011シンポジウム
  • Place of Presentation: 和光(招待講演)
  • Year and Date: 2011-12-09
• [Presentation] 細菌由来複合糖質糖鎖の合成研究 (2011)
  • Author(s): 石渡明弘, 伊藤幸成
  • Organizer: 京都大学グローバル COE-基幹研究所 合同シンポジウム
  • Place of Presentation: 和光(poster)
  • Year and Date: 2011-01-28
• [Presentation] 細菌由来複合糖質糖鎖の合成研究 (2011)
  • Author(s): 石渡明弘、伊藤幸成
  • Organizer: 理研・基幹研究所-京都大学グローバルCOE合同シンポジウム
  • Place of Presentation: 和光
  • Year and Date: 2011-01-28
• [Presentation] Strategies toward stereoselective construction of complex bacterial glycans (2011)
  • Author(s): Ishiwata, A.
  • Organizer: 14th Asian Chemical Congress 2011
  • Place of Presentation: Bangkok, Thailand(Invited)
• [Presentation] 結核菌細胞壁多糖アラビナンの合成研究 (2011)
  • Author(s): 石渡明弘, 伊藤幸成
  • Organizer: 第30回日本糖質学会年会
  • Place of Presentation: 長岡(poster)
• [Presentation] 結核菌由来アラビナン8糖フラグメントの合成とフラグメントカップリング (2011)
  • Author(s): 石渡明弘, 伊藤幸成
  • Organizer: 日本農芸化学会2011年度大会
  • Place of Presentation: 京都
• [Presentation] 結核菌由来アラビナン分岐7糖フラグメント構築へ向けた分子内アグリコン転移反応の応用 (2011)
  • Author(s): 石渡明弘, 伊藤幸成
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 横浜
• [Presentation] Synthetic study of pseudaminic acid from bacterial glycoprotein (2011)
  • Author(s): Lee, Y. J.; Kubota, A.Lee, Y. J.; Kubota, A.; Ishiwata, A.; Ito, Y.
  • Organizer: 第52回天然有機化合物討論会
  • Place of Presentation: 静岡(poster &amp; short talk)
• [Presentation] 結核菌細胞壁多糖アラビナンの合成研究 (2011)
  • Author(s): 石渡明弘, 伊藤幸成
  • Organizer: 第30回日本糖質学会年会
  • Place of Presentation: 長岡
• [Presentation] Strategies toward stereoselective construction of complex bacterial glycans (2011)
  • Author(s): Ishiwata, Akihiro
  • Organizer: 14th Asian Chemical Congress 2011
  • Place of Presentation: Bangkok, Thailand(招待講演)
• [Presentation] 結核菌由来アラビナン8糖フラグメントの合成とフラグメントカップリング (2011)
  • Author(s): 石渡明弘、伊藤幸成
  • Organizer: 2011年度農芸化学会大会
  • Place of Presentation: 京都
• [Presentation] NAP エーテルを介する分子内アグリコン転移反応を利用した、β-マンノシル化の検討 (2010)
  • Author(s): 石渡明弘, 櫻井絢花, 李龍柱, 伊藤幸成
  • Organizer: GlycoTOKYO2010 シンポジウム
  • Place of Presentation: 東京(poster)
  • Year and Date: 2010-11-27
• [Presentation] NAPエーテルを介する分子内アグリコン転移反応を利用した、β-マンノシル化の検討 (2010)
  • Author(s): 石渡明弘、櫻井絢花、李龍柱、伊藤幸成
  • Organizer: GlycoTokyo 2010
  • Place of Presentation: 東京
  • Year and Date: 2010-11-27
• [Presentation] Synthetic study of mycobacterial arabinan (2010)
  • Author(s): Ishiwata, A.; Ito Y.
  • Organizer: 25^<th> International Carbohydrate Symposium
  • Place of Presentation: Chiba, Japan
  • Year and Date: 2010-08-15
• [Presentation] Synthetic study of mycobacterial arabinan (2010)
  • Author(s): Ishiwata, A.; Ito, Y.
  • Organizer: PACIFICHEM2010
  • Place of Presentation: Hawaii, USAGlycoTOKYO2010 シンポジウム,
• [Presentation] Accelerated glycosylation under frozen conditions: Effect on stereoselectivity and velocity of O-glycosylation (2010)
  • Author(s): Ishiwata, A.; Sakurai, A.; Durr, K.; Ito, Y.
  • Organizer: PACIFICHEM 2010
  • Place of Presentation: Hawaii, USA
• [Presentation] 細菌由来複合糖質糖鎖の合成研究 (2010)
  • Author(s): 石渡明弘
  • Organizer: 第59回高分子討論会
  • Place of Presentation: 札幌,(招待講演)
• [Presentation] Synthetic study of mycobacterial arabinan (2010)
  • Author(s): Ishiwata, A.; Ito, Y.
  • Organizer: International Carbohydrate Symposium
  • Place of Presentation: Tokyo
• [Presentation] Effects of frozen conditions on stereoselectivity and velocity of O-glycosylation reactions (2010)
  • Author(s): Sakurai, A.; Durr, K.; Ishiwata, A.; Ito, Y.
  • Organizer: 25^<th> International Carbohydrate Symposium
  • Place of Presentation: Chiba, Japan
• [Presentation] 細菌由来複合糖質糖鎖の合成研究 (2010)
  • Author(s): 石渡明弘
  • Organizer: 第59回高分子討論会
  • Place of Presentation: 札幌
• [Presentation] Synthetic study of mycobacterial arabinan (2010)
  • Author(s): Ishiwata, A.; Ito, Y.
  • Organizer: PACIFICHEM 2010
  • Place of Presentation: Hawaii, USA
• [Presentation] Effects of frozen conditions on stereoselectivity and velocity of O-glycosylation reactions (2010)
  • Author(s): Ishiwata, A.; Sakurai, A.; Durr, K.; Ito, Y.
  • Organizer: PACIFICHEM 2010
  • Place of Presentation: Hawaii, USA
• [Remarks] Org. Biomol. Chem. 2010, 8, 3596-3608に掲載さ れた高選択的グリコシル化反応に関する論文 (論文 7)は表紙に採用された.
• [Remarks] J. Am. Chem. Soc. 2011, 133, 2275-2291.に掲載さ れた結核菌多糖の合成に関する論文 (論文 6)はRIKEN RESEARCH で紹介された。
  • URL: http://www.rikenresearch.riken.jp/jpn/research/6871
• [Remarks] J. Am. Chem. Soc. 2011, 133, 19524-19535.に掲載さ れた不凍糖の合成と構造解析に関する論文 (論文 4)はAsian Research News, 2012. 12.で紹介された。また、RIKEN RESEARCH で紹介された。
  • URL: http://www.rikenresearch.riken.jp/eng/research/6592
• [Remarks] 理化学研究所 ホームページ
  • URL: http://www.riken.jp/
• [Remarks] RIKEN RESEARCH : 甲虫の不凍物質を作る
  • URL: http://www.rikenresearch.riken.jp/jpn/research/6871
• [Remarks] RIKEN RESEARCH : Sugar synthesis hits ,,,
  • URL: http://www.rikenresearch.riken.jp/eng/research/6592
• [Remarks]
  • URL: http://www.riken.jp/asi/jp/index.html
• [Remarks]
  • URL: http://www.riken.jp/asi/jp/index.html