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Technological development of oligosaccharide units as biomaterials of life science

Research Project

Project/Area Number 09556021
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section展開研究
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionShizuoka University

Principal Investigator

USUI Taichi  Shizuoka University, Faculty of Agriculture, Professor, 農学部, 教授 (50111802)

Co-Investigator(Kenkyū-buntansha) SUZUKI Yasuo  University of Shizuoka, Faculty of Pharmaceuitical, Professor, 薬学部, 教授 (00046278)
KOBAYASHI Kazukiyo  Nagoya University, Graduate School of Engineering, Professor, 大学院・工学研究科, 教授 (10023483)
MURATA Takeomi  Shizuoka University, Faculty of Agriculture, Assistant Professor, 農学部, 助手 (30273171)
AJISAKA Katsumi  Meiji Milk Products Co., Ltd., Meiji Institute of Health Science, Research Manager, ヘルスサイエンス研究所, 室長
鰺坂 勝美  明治乳業ヘルスサイエンス研究所, 室長
Project Period (FY) 1997 – 1999
Project Status Completed (Fiscal Year 1999)
Budget Amount *help
¥11,400,000 (Direct Cost: ¥11,400,000)
Fiscal Year 1999: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 1998: ¥2,700,000 (Direct Cost: ¥2,700,000)
Fiscal Year 1997: ¥7,500,000 (Direct Cost: ¥7,500,000)
KeywordsGlycotechnology / Biomaterial / Glycoconjugate / Oligosacchride unit / Enzymatic synthesis / Glycopolymer / Molecular recognition / Molecular design / Oligosaccharide unit / Glycopolymor / Oligosaccharide library / Oligosaccharide Unit / Enzymatic Synthesis / Molecular Recognition / Molecular Design
Research Abstract

Our purpose is to prepare oligosaccharide units library folowing practical synthesis of biologically important oligosaccharides essentially for developing glycobology and glycottechnolog. The synthesis of possible array of linkages of (1-3), (1-4) and (1-6) of β-D-Gal-D-GlcNAc and β-D-Gal-D-GalNAc was done by using some readily available β-D-galactosidases. The preparation of the galactosyl-disaccharide units library led to the enzymatic synthesis of trisaccharides containing GlcNAc; β-D-GlcNAc-(1-3)-β-D-Gal-(1-4)-GlcNAc as a common unit of polylacto- saminoglycan and β-D-Gal-(1-3)-[β-D-GlcNAc-(1-6)]-α-D-GalNAc-OCィイD26ィエD2HィイD24ィエD2NOィイD22ィエD2-p as a carbohydrate unit of mucin type 2 core. Transglycosylation of L-Fuc to LacNAc and lactose utilizing α-L-fucosidases also produced α-L-fucosyl-N-acetyllactosamine and 3'-O-α-L-fucosyllactose. Furthermore, as a synthetic strategy of human milk oligosaccharide, lacto-N-tetraose (β-D-Gal-(1-3)-β-D-GlcNAc-(1-3)-β-D-Gal-(1-4)-D-Glc)and lacto-N-neotetraose(β-D-Gal-(1-4)-β-D-GlcNAc-(1-3)-β-D-Gal-(1-4)-D-Glc) were practically synthesized by a combination of glycosyltransferase catalyzed reaction and glycosidase-catalyzed transglycosylation from lactose as an initial substance.
Such synthetic oligosaccharides available in large amounts were used to synthesize glycopolymer. chemo-enzymatic synthesis of glycopeptides carrying LacNAc unit as a model of asialoglycoprotein, and β-D-Gal-(1-3)-α-D-GalNAc and α-NeuAc-(1-3)-β-D-Gal-(1-3)-α-D-GalNAc units as models of mucin-type glycoproteins was carried out by introducing these oigosaccharides as side chain into polyglutamic acid as main chain. The artgificial glycopolypeptides were shown to be useful as probes of carbohydrate recognition and modeling in the analysis of glycoprotein-lectin interactions.

Report

(4 results)
  • 1999 Annual Research Report   Final Research Report Summary
  • 1998 Annual Research Report
  • 1997 Annual Research Report
  • Research Products

    (33 results)

All Other

All Publications (33 results)

  • [Publications] Y.Zeng, T.Usui el al: "Regioselsctive synthesis of p-nitrophenyl glycoside of β-D-galactopyranosyl-disaccharide by use of transgoycosylation of β-D-galactosidase"Carbohydrate Researsh. 325. 120-131 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T.Murata, T.Usui et al: "Enzymatic synthesis of O-α-L-fucosyl N-acetyllactosamine and 3'-O-α-L-fucosyllactose utillizing α-L-fucosiidase"Carbohydrate Research. 320. 192-199 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T.Murata, T.Usui et al: "Facile enzymatc conversion of lactose into lacto-N-tetraose and lacto-N-tetraose"Glycoconjugate Journal. 16. 189-195 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] X.Zeng, T.Usui et al: "Analysis of specific interaction of synthetic glycopeptides carrying N-acetyllactosamine and related compouds with lectins"Carbohydrate Research. 325. 120-131 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] X.Zeng, T.Usui et al: "Synthesis of artificial N-glycopeptides carrying N-acetyllactosamine and its related compounds and their specific interaction with lectins"Bioscience Biotechnology Biochemistry. 62. 1171-1178 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T.Murata, T.Usui et al: "Enzymatic synthesis of β-D-Gal-(1--3)-[β-D-GlcNAc-(1-6)]-α-D-GalNAc-OC_6H_4NO_2-p as a carbohydate unit of mucin-type 2 core"Glycoconjugate Journal. 15. 575-582 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] 碓井泰市: "酵素を用いた糖および糖鎖の合成(分担)"学会出版センター 「生理活性糖鎖研究法」. 7 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] X. Zheg, R. Yoshhino T. Murata, K. Ajisaka and T. Usui: "Regioselective synthesis of p-nitrophenyl glycoside of β-D-galactopyranosyl-disaccharide by use of transglycosylation of β-D-galactosidase"Carbohydr. Res.. 325. 120-131 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T. Murata, S. Morimoto, Zeng, S. Watanabe and T. Usui: "Enzymatic synthesis of O-α-L-fucosyl N-acetyllactosamine and 3'-O-α-L-fucosyllactose utillizing α-L-fucosiidase"Carbohydr. Res.. 320. 192-199 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T. Murata, T. Inukai, T. Suzuki, S. M. Yamagishi and T. Usui: "Facile enzymatc conversion of lactose into lacto-N-tetraose and lacto-N-tetraose"Glycoconjugate J.. 16. 189-195 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] X. Zeng, T. Murata, H. Kawagishi, T. Usui and K. Kobayashi: "Analysis of specific interaction of synthetic glycopeptides carrying N-acetyllactosamine and related compounds with] lectins"Carbohydr. Res.. 325. 120-131 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] X. Zeng, T. Murata, H. Kawagishi, T. Usui and K. Kobayashi: "Synthesis of artificial N-glycopeptides carrying N-acetyl-lactosamine and its related compounds and their specific interaction with lectins"Biosci. Biotech. Biochem.. 62. 1171-1178 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T. Murata, T. Itoh and T. Usui: "Enzymatic synthesis of β-D-Gal-(1-3)-[β-D-GlcNAc-(1-6)]-α-D-GalNAc-OCィイD26ィエD2HィイD24ィエD2NOィイD22ィエD2-pas a carbohydrate unit of mucin-type 2 core"Glycoconjugate J.. 15. 575-582 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T. Usui: ""Synthesis of glycan chain using enzyme" (in Japanese)""Research of biological active glycan" ed by Gakaishuppan center.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Murata,T.inukai,T.,Suzuki,M.,Yamagishi,M.,and Usui,T: "Facile enzymatic conversion of lactose into lacto-N-tetraose and lacto-N-neotetraose"Glycoconjugate J.. 16. 189-195 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Murata,T.,Morimoto,S,,Zeng,X,Watanabe,S.,and Usui,T: "Enzymatic synthesis of O-α-L-fucosyl N-acetyllactosamine and 3'-O-α-L-fucosyllactose utilizing α-L-fucosidases"Carbohydr.Res.. 320. 192-199 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Takada M.,Ogawa K.,Saito S.,Murata T.,and Usui T.: "Chemo-enzymatic synthesis of 6^3-O-benzyl and 6^3-O-β-D-galactosyl-maltotrionolactones as inhibitors for human α-amylases"J.Carbohydr.Chem.. 18. 149-163 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Murata,T.,Shimada M.,Watanabe N.,Sakata K.,and Usui T.: "Practical enzymatic synthesis of primeverose annd its glycoside"J.Appl.Glycosci.. 46. 431-437 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Zeng X.,Yoshino R.,Murata T.,Ajisaka K.Usui T.: "Regioselective synthesis of p-nitrophenyl glycoside of β-D-galactopyranosyl-disaccharide by use of transglycosylation of"Carbohydr.Res.. 325. 120-131 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] Ashida H.,Yamamoto K.,Murata T.,Usui T.,and Kumagai H.: "Characterization of endo-N-acetylgalactosaminidase from Bacillus sp.and symtheses of neo-oligosaccharides using its transglycosylation"Arch.Biochem.Biophys.. 373. 394-400 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] 碓氷 泰市: "酵素を用いた糖および糖鎖の合成(分担)"学会出版センター 「生理活性糖鎖研究法」. 7 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] T.Murata, T.Itho,and T.Usui: "Enzymatic synthesis of β-D-Gal-(1-3)-[β-D-GlcNAc-(1-6)-α-D-GalNAc-OC_6H_4NO_2-ρ as a carbohydrate unit of mucin-type 2 core" Glycoconjugate J.15. 575-582 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] X.Zeng, T Usui et.al.: "Synthesis of artificial N-glycopolypeptide carrying N-acctyllactosamine and related compounds and their specific interactions with lectins" Biosci.Biotech.Biochem.62. 1171-1178 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] A.Tsuchida, S.Akimoto, T.Usui and K.Kobayashi: "Synthesis of artificial glycoconjugate polymers starting from enzymatically synthesized oligosaccharides and their interactions with lectins" J.Biochem.123. 715-721 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] K.Kobayashi, S.Kamiya, M.Matsuyama, T.Murata and T.Usui: "Synthesis and function of a glycopolymer carrying Galβ1-4(GlcNAc)_3 tetrasaccharide" Polymer J.30. 653-658 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] X Zeng, T.Murata, H.Kawagishi, T.Usui and K.Kobayashi: "Analysis of specific interaction of synthetic glycopeptides carrying N-acetyllactosamine and related compounds with lectins" Carbohydr.Res.312. 209-217 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] T.Murata, T.Inukai, M.Suzuki, M.Yamagishi and T.Usui: "Facile enzymatic conversion of lactose into lacto-N-tetraose and lacto-N-neotetraose" Glycoconjugate J.,accepted for publication.

    • Related Report
      1998 Annual Research Report
  • [Publications] T.Murata, A.Tashiro, T.Itho and T.Usui: "Enzymatic synthesis of 3'-O- and 6'-O-N-acetylglucosaminyl-N-acetyl-lactosaminide glycoside catalyzed by -NAHase" Biochim.Biophys.Acta. 1335. 326-334 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] T.Murata and T.Usui: "Oligosaccharide units library and its utilization" Biosci.Biotech.Biochem.61. 607-615 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] K.Kobayashi, E.Tawada, T.Akaike and T.Usui: "Artificial glycopeptide conjugate:simple synthesis of lactose-and N,N'- -glycoside linkages and their interaction with lectins" Biochim.Biophys.Acta. 1336. 117-122 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] K.Kobayashi, A.Tsuchida, T.Usui and T.Akaike: "A new type of artificial glycoconjugate polymer:a covenient synthesis and its interaction with lectins" Macromolecules. 30. 2016-2020 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] T.Murata, T.Itho and T.Usui: "Enzymatic synthesis of -D-Gal-(1-3)-[ -D-GlcNAc-(1-6)- -D-GalNAc-OC_6H_4NO_2-p as a carbohydrate unit of mucin-type 2 core" Glycoconjugate J.(in press).

    • Related Report
      1997 Annual Research Report
  • [Publications] Z.Xiaoxiong et al.: "Synthesis of artificial N-glycopolypeptides carrying N-acetyl-lactosamine and its related compounds and their specific interaction" Biosci.Biotech.Biochem.(in press).

    • Related Report
      1997 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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