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2003 Fiscal Year Final Research Report Summary

Organic Synthesis of Glycoprotein Structural Motifs

Research Project

Project/Area Number 13480191
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioorganic chemistry
Research InstitutionRIKEN(The Institute of Physical and Chmical Resarch)

Principal Investigator

ITO Yukishige  RIKEN, Synthetic Cellular Chemistry Laboratory, Chief Scientist, 伊藤細胞制御化学研究室, 主任研究員 (80168385)

Co-Investigator(Kenkyū-buntansha) MATSUO Ichiro  RIKEN, Synthetic Cellular Chemistry Laboratory, Senior Resaehc Scientist, 伊藤細胞制御化学研究室, 研究員 (40342852)
MANABE Shino  RIKEN, Synthetic Cellular Chemistry Laboratory, Senior Resaehc Scientist, 伊藤細胞制御化学研究室, 研究員 (60300901)
ISHIWATA Akihiro  RIKEN, Synthetic Cellular Chemistry Laboratory, Resaehc Scientist, 伊藤細胞制御化学研究室, 研究員 (70342748)
Project Period (FY) 2001 – 2003
Keywordsglycoprotein / quality control / chaperone / asparagine-linked / gglycan chain / stereoselctive synthesis / glycopeptide / C-mannosyl tryptophan
Research Abstract

The aim of this study was to develop methodologies for the synthesis of glycoprotein glycans and related molecular probes. The following results were obtained.
1. Synthesis of asparagines-linked glycoprotein glycans: Proposed ligand structure of ER chaperones calnexin and calreticulin was synthesized. Analysis of specific interaction was investigated. Octamarnnrosylated glycans, which are hypothesized to be involved n the recognition of EDEM/Htm1p were synthesized.
2. Methodologies for efficient synthesis of glycpeptide Novel methods for the construction of oligosaccharide-asparagine linkage, chenroselctive peptide bond formation using thioester, and peptide elongation on sold support were developed.
3. Synthesis of C-mannnosyl tryptophan (CMW) and its derivatives: Various types of CMW-containing glycopeptides, as well as glucose analogue of CMW were synthesized.
4. Methods for the facile synthesis of oligosaccharide: New types of linkers, methods for the real-time monitoring of polymer-support oligosacharide synthesis, and capture release purification methods were developed.
5. Synthesis of enzyme inhibitors: Bisubstrate-type derivatives of sialyltransferases were synthesized systematically, and their activities were examined.

  • Research Products

    (64 results)

All 2003 2002 2001

All Journal Article (62 results) Book (2 results)

  • [Journal Article] A novel method for the formation of N-glycosides using hydroxamate2003

    • Author(s)
      J.Nakano, T.Ichiyanagi, H.Ohta, Y.Ito
    • Journal Title

      Tetrahedron Lett. 44

      Pages: 2853-2856

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Selective synthesis of peptide bond by using formyl-substituted phenylthioester2003

    • Author(s)
      A.Ishiwata, T.Ichiyanagi, Y.Ito
    • Journal Title

      Peptide Science 42

      Pages: 25-28

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Synthesis of monoglucosylated high-mannose-type dodecasaccharide, a putative ligand for molecular chaperone, calnexin, and calreticurin2003

    • Author(s)
      I.Matsuo, M.Wada, S.Manabe, Y.Yamaguchi, K.Otake, K.Kato, Y.Ito
    • Journal Title

      J.Am.Chem.Soc. 125

      Pages: 3402-3403

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Total synthesis of mannosyl tryptophan and its derivatives2003

    • Author(s)
      S.Manabe, Y.Marui, Y.Ito
    • Journal Title

      Chem.Eur.J. 9

      Pages: 1435-1447

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Pentafluoropropionyl and trifluoroacetyl groups for temporary hydroxyl group protection in oligomannoside synthesis2003

    • Author(s)
      M.Takatani, I.Matsuo, Y.Ito
    • Journal Title

      Carbohydr.Res. 338

      Pages: 1073-1081

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Chemoselective peptide bond formation using formyl-substituted nitrophenylthio ester2003

    • Author(s)
      A.Ishiwata, T.Ichiyanagi, M.Takatani, Y.Ito
    • Journal Title

      Tetrahedron Lett. 44

      Pages: 3187-3190

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] グリコシル化2003

    • Author(s)
      眞鍋史乃, 伊藤幸成
    • Journal Title

      ファルマシア 39

      Pages: 680-681

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Polymer-resin hybrid capture - Release strategy for rapid oligosaccharide construction2003

    • Author(s)
      S.Hanashima, S.Manabe, Y.Ito
    • Journal Title

      Synlett

      Pages: 979-982

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Systematic syntheses and inhibitory activities of bisubstrate-type inhibitors of sialyltransferases2003

    • Author(s)
      H.Hinou, X.-L.Sun, Y.Ito
    • Journal Title

      J.Org.Chem. 68

      Pages: 5602-5613

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Preparation of sialyl donors carrying functionalized ester substituents : Effects on the selectively of glycosylation2003

    • Author(s)
      A.Ishiwata, Y.Ito
    • Journal Title

      Synlett

      Pages: 1339-1343

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 糖タンパク質糖鎖の生体機能と精密合成:糖タンパク質品質管理機構の解明を目指して2003

    • Author(s)
      松尾一郎, 伊藤幸成
    • Journal Title

      日本農芸化学会誌 77

      Pages: 983-987

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Synthesis of an octamannosyled glycan chain, the key oligosaccharide structure in ER-associated degradation2003

    • Author(s)
      I.Matsuo, Y.Ito
    • Journal Title

      J Carbohydr.Res. 338

      Pages: 2163-2168

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] The novel glycoprotein structure ; C-Mannosyl tryptophan2003

    • Author(s)
      S.Manabe, Y.Ito
    • Journal Title

      Trends in Glycoscience and Glycotechnology 15

      Pages: 181-196

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Approaches to intramolecular sialylation 2. Synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid containing an unprotected carboxy group2003

    • Author(s)
      L.O.Kononov, A.M.Shpirt, Y.Ito, T.Ogawa
    • Journal Title

      Russ.Chem.Bull., Int.Ed. 52

      Pages: 1442-1446

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] A novel method for the formation of N-glycosides using hydroxamate2003

    • Author(s)
      Jun Nakano, Tsuyoshi Ichiyanagi, Hiromichi Ohta, Yukishige Ito
    • Journal Title

      Tetrahedron Lett. 44

      Pages: 2853-2856

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Selective synthesis of peptide bond by using formyl-substituted phenylthio ester2003

    • Author(s)
      Akihiro Ishiwata, Tsuyoshi Ichiyanagi, Yukishige Ito
    • Journal Title

      Peptide Science 2002

      Pages: 25-28

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthesis of monoglucosylated high-mannose-type dodecasaccharide, a putative ligand for molecular chaperone, calnexin, and calreticurin2003

    • Author(s)
      Ichiro Matsuo, Megumi Wada, Shino Manabe, Yoshiki Yamaguchi, Keisuke Otake, Koichi Kato, Yukishige Ito
    • Journal Title

      J. Am. Chem. Soc. 125

      Pages: 3402-3403

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Total synthesis of mannosyl tryptophan and its derivatives2003

    • Author(s)
      Shino Manabe, Yoshihiko Marui, Yukishige Ito
    • Journal Title

      Chem. Eur. J. 9

      Pages: 1435-1447

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Pentafluoropropionyl and trifluoroacetyl groups for temporary hydroxyl group protection in oligomannoside synthesis2003

    • Author(s)
      Maki Takatani, Ichiro Matsuo, Yukishige Ito
    • Journal Title

      Carbohydr. Res. 338

      Pages: 1073-1081

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Chemoselective peptide bond formation using formyl-substituted nitrophenylthio ester2003

    • Author(s)
      Akihito Ishiwata, Tsuyoshi Ichiyanagi, Maki Takatani, Yukishige Ito
    • Journal Title

      Tetrahedron Lett. 44

      Pages: 3187-3190

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Polymer-resin hybrid capture - Release strategy for rapid oligosaccharide construction2003

    • Author(s)
      Shinya Hanashima, Shino Manabe, Yukishige Ito
    • Journal Title

      Synlett

      Pages: 979-982

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Systematic syntheses and inhibitory activities of bisubstrate-type inhibitors of sialyltransferases2003

    • Author(s)
      Hiroshi Hinou, Xue-Long Sun, Yukishige Ito
    • Journal Title

      J. Org. Chem. 68

      Pages: 5602-5613

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Preparation of sialyl donors carrying functionalized ester substituents: Effects on the selectivity of glycosylation2003

    • Author(s)
      Akihiro Ishiwata, Yukishige Ito
    • Journal Title

      Synlett

      Pages: 1339-1343

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Chemical synthesis of asparagine-linked glycoprotein oligosaccharides: Recent examples2003

    • Author(s)
      Yukishige Ito, Ichiro Matsuo
    • Journal Title

      Carbohydrate-based Drug Discovery

      Pages: 253-280

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthesis of an octamannosyled glycan chain, the key oligosaccharide structure in ER-associated degradation2003

    • Author(s)
      Ichiro Matsuo, Yukishige Ito
    • Journal Title

      Carbohydr. Res. 338

      Pages: 2163-2168

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] The novel glycoprotein structure; C-Mannosyl tryptophan2003

    • Author(s)
      Shino Manabe, Yukishige Ito
    • Journal Title

      Trends in Glycosci. & Glycotech. 15

      Pages: 181-196

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Approaches to intramolecular sialylation 2. Synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid containing an unprotected carboxy group2003

    • Author(s)
      LO.Kononov, A.M.Shpirt, Y.Ito, T.Ogawa
    • Journal Title

      Russ. Chem. Bull., Int. Ed. 52

      Pages: 1442-1446

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Preparation of glycosylated amino acid derivatives for glycoprotein synthesis by in Vitro translation system2002

    • Author(s)
      S.Manabe, K.Sakamoto, Y.Nakahara, M.Sisido, T.Hohsaka, Y.Ito
    • Journal Title

      Bioorg. & Med.Chem. 10

      Pages: 573-581

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Tag-reporter and resin capture-release strategy in oligosaccharide synthesis2002

    • Author(s)
      Y, Ito, S.Manabe
    • Journal Title

      Chem.Eur.J. 8

      Pages: 3076-3084

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Synthesis of N-linked glycosyl asparagin derivatives with unproteted sugar components2002

    • Author(s)
      A.Ishiwata, M.Takatani, Y.Nakahara, Y.Ito
    • Journal Title

      SYNLETT

      Pages: 634-636

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Desilylation under high pressure2002

    • Author(s)
      I.Matsuo, M.Wada, Y.Ito
    • Journal Title

      Tetrahedron Lett. 43

      Pages: 3273-3275

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Synthesis of mucin-type glycopeptide (β hCG 130-145) by one-resin fragment condensation of the glycopeptide segments carrying unmasked oligosaccharides2002

    • Author(s)
      T.Ichiyanagi, M.Takatani, K.Sakamoto, Y.Nakahara, Y.Ito, H.Hojo, Y.Nakahara
    • Journal Title

      Tetrahedron Lett. 43

      Pages: 3297-3300

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Combination of silyl carbamate and amino acid fluoride for solid-phase peptide synthesis2002

    • Author(s)
      K.Sakamoto, Y.Nakahara, Y.Ito
    • Journal Title

      Tetrahedron Lett. 43

      Pages: 1515-1518

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 糖鎖合成における新しい迅速合成法の開発2002

    • Author(s)
      伊藤幸成, 眞鍋史乃
    • Journal Title

      有機合成化学協会誌 60

      Pages: 476-477

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] E3 ubiquitin ligase that recognizes sugar chains2002

    • Author(s)
      Y.Yoshida, T.Chiba, F.Tokunaga, H.Kawasaki, K.Iwai, T.Suzuki, Y.Ito, K.Matsuoka, M.Yoshida, K.Tanaka, T.Tai
    • Journal Title

      Nature 418

      Pages: 438-442

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Novel substrates for efficient enzymatic transglucosylation by Bacillus circulans2002

    • Author(s)
      S.Komba, Y.Ito
    • Journal Title

      Can.J.Chem. 80

      Pages: 1174-1185

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] On-Rsin Real-Time Reaction Monitoring of Solid-Phase Oligosacharide Synthesis2002

    • Author(s)
      S.Manabe, Y.Ito
    • Journal Title

      J.Am.Chem.Soc. 124

      Pages: 12638-12639

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Bisubstrate-type inhibitor of sialytransferases2002

    • Author(s)
      H.Hinou, X.-L.Sun, Y.Ito
    • Journal Title

      Tetrahedron Lett. 43

      Pages: 9147-9150

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Preparation of glycosylated amino acid derivatives for glycoprotein synthesis by in Vitro translation system2002

    • Author(s)
      Shino Manabe, Kimitoshi Sakamoto, Yoshiaki Nakahara, Masahiko Sisido, Takahiro Hohsaka, Yukishige Ito
    • Journal Title

      Bioorg. & Med. Chem. 10

      Pages: 573-581

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Tag-reporter and resin capture-release strategy in oligosaccharide synthesis2002

    • Author(s)
      Yukishige Ito, Shino Manabe
    • Journal Title

      Chem. Eur. J. 8

      Pages: 3076-3084

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthesis of N-linked glycosyl asparagin derivatives with unproteted sugar components2002

    • Author(s)
      Akihiro Ishiwata, Maki Takatani, Yoshiaki Nakahara, Yukishige Ito
    • Journal Title

      SYNLETT

      Pages: 634-636

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Desilylation under high pressure2002

    • Author(s)
      Ichiro Matsuo, Megumi Wada, Yukishige Ito
    • Journal Title

      Tetrahedron Lett. 43

      Pages: 3273-3275

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthesis of mucin-type glycopeptide (β hCG 130-145) by one-resin fragment condensation of the glycopeptide segments carrying unmasked oligosaccharides2002

    • Author(s)
      Tsuyoshi Ichiyanagi, Maki Takatani, Kimitoshi Sakamoto, Yuko Nakahara, Yukishige Ito, Hironobu Hojo, Yoshiaki Nakahara
    • Journal Title

      Tetrahedron Lett. 43

      Pages: 3297-3300

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Combination of silyl carbamate and amino acid fluoride for solid-phase peptide synthesis2002

    • Author(s)
      Kimitoshi Sakamoto, Yoshiaki Nakahara, Yukishige Ito
    • Journal Title

      Tetrahedron Lett. 43

      Pages: 1515-1518

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] E3 ubiquitin ligase that recognizes sugar chains2002

    • Author(s)
      Yukiko Yoshida, Tomoki Chiba, Fuminori Tokunaga, Hiroshi Kawasaki, Kazuhiro Iwai, Toshiaki Suzuki, Yukishige Ito, Koji Matsuoka, Minoru Yoshida, Keiji Tanaka, Tadashi Tai
    • Journal Title

      Nature 418

      Pages: 438-442

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Novel substrates for efficient enzymatic transglycosylation by Bacillus circulans2002

    • Author(s)
      Shiro Komba, Yukishige Ito
    • Journal Title

      Can. J. Chem. 80

      Pages: 1174-1185

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] On-Rsin Real-Time Reaction Monitoring of Solid-Phase Oligosaccharide Synthesis2002

    • Author(s)
      Shino Manabe, Yukishige Ito
    • Journal Title

      J. Am. Chem. Soc. 124

      Pages: 12638-12639

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Bisubstrate-type inhibitor of sialyltransferases2002

    • Author(s)
      Hiroshi Hinou, Xue-Long Sun, Yukishige Ito
    • Journal Title

      Tetrahedron Lett. 43

      Pages: 9147-9150

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] A new method for formacetal linkage formation : protection of alcohols, phenols and carboxylic acids2001

    • Author(s)
      D.Sawada, Y.Ito
    • Journal Title

      Tetrahedron Lett. 42

      Pages: 2501-2504

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] On the mechanism of p-methoxybenzylidene assisted intramolecular aglycon delivery2001

    • Author(s)
      Y.Ito, H.Ando, M.Wada, T.Kawai, Y.Ohnishi, Y.Nakahara
    • Journal Title

      Tetrahedron 57

      Pages: 4123-4132

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Tag-reporter strategy for facile oligosaccharide synthesis on polymer support2001

    • Author(s)
      H.Ando, S.Manabe, Y.Nakahara, Y.Ito
    • Journal Title

      J.Am.Chem.Soc. 123

      Pages: 3848-3849

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Wang resin-type linker containing a nitro group for polymer supprtoligosaccharide synthesis : Polymer-supported glucosyl donor2001

    • Author(s)
      S.Manabe, Y.Ito
    • Journal Title

      Chem.Phram.Bull. 49

      Pages: 1234-1235

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 糖鎖固相反応における新規手法の開発2001

    • Author(s)
      眞鍋史乃, 伊藤幸成
    • Journal Title

      ファルマシア 37

      Pages: 884-888

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] β-Galactosidase-catalyzed intramolecular transglycosylation2001

    • Author(s)
      S.Komba, Y.Ito
    • Journal Title

      Tetrahedron Lett. 42

      Pages: 8501-8505

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Solid-phase capture-release strategy applied to oligosaccharide synthesis on a soluble polymer support2001

    • Author(s)
      H.Ando, S.Manabe, Y.Nakahara, Y.Ito
    • Journal Title

      Angew.Chem.Int.Ed. 40

      Pages: 4725-4728

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] A new method for formacetal linkage formation: protection of alcohols, phenols and carboxylic acids2001

    • Author(s)
      Daisuke Sawada, Yukishige Ito
    • Journal Title

      Tetrahedron Lett. 42

      Pages: 2501-2504

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] On the mechanism of p-methoxybenzylidene assisted intramolecular aglycon delivery2001

    • Author(s)
      Yukishige Ito, Hiromune Ando, Megumi Wada, Tsubasa Kawai, Yuki Ohnish, Yoshiaki Nakahara
    • Journal Title

      Tetrahedron 57

      Pages: 4123-4132

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Tag-reporter strategy for facile oligosaccharide synthesis on polymer support2001

    • Author(s)
      Hiromune Ando, Shino Manabe, Yoshiaki Nakahara, Yukishige Ito
    • Journal Title

      J.Am.Chem.Soc. 123

      Pages: 3848-3849

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Wang resin-type linker containing a nitro group for polymer supprt oligosaccharide synthesis: Polymer-supported glycosyl donor2001

    • Author(s)
      Shino Manabe, Yukishige Ito
    • Journal Title

      Chem. Pharm. Bull. 49

      Pages: 1234-1235

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] β-Galactosidase-catalyzed intramolecular transglycosylation2001

    • Author(s)
      Shiro Komba, Yukishige Ito
    • Journal Title

      Tetrahedron Lett. 42

      Pages: 851-8505

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Solid-phase capture-release strategy applied to oligosaccharide synthesis on a soluble polymer support2001

    • Author(s)
      Hiromune Ando, Shino Manabe, Yoshiaki Nakahara, Yukishige Ito
    • Journal Title

      Angew. Chem. Int. Ed. 40

      Pages: 4725-4728

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthesis of enediyne antibiotic oligosaccharides2001

    • Author(s)
      Yukishige Ito, Shino Manabe
    • Journal Title

      Chemistry and Chemical Biology III

      Pages: 2441-2469

    • Description
      「研究成果報告書概要(欧文)」より
  • [Book] Carbonhydrate-based Drug Discovery2003

    • Author(s)
      Y.Ito, I.Matsuo
    • Total Pages
      253-280
    • Publisher
      WILEY-VCH
    • Description
      「研究成果報告書概要(和文)」より
  • [Book] Glycoscience : Chemistry and Chemical Biology III2001

    • Author(s)
      Y.Ito, S.Manabe
    • Total Pages
      2441-2469
    • Publisher
      Springer
    • Description
      「研究成果報告書概要(和文)」より

URL: 

Published: 2006-07-11  

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