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Chemical modification of oligosaccharide chains of N-aspargine-type glycoproteins

Research Project

Project/Area Number 06453142
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionKeio University

Principal Investigator

OGAWA Seiichiro  Keio University, Faculty of Science and Technology, Professor, 理工学部, 教授 (00051475)

Project Period (FY) 1994 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥5,600,000 (Direct Cost: ¥5,600,000)
Fiscal Year 1996: ¥1,600,000 (Direct Cost: ¥1,600,000)
Fiscal Year 1995: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 1994: ¥2,600,000 (Direct Cost: ¥2,600,000)
KeywordsCarbohydrate mimics / Carba-sugars / Pseudo-sugars / Cyclitols / Glycosidase inhibitors / Glycosyltransferases / Carbaoligosaccharides / カルバ糖(擬似糖) / カルバ糖(擬似糖質)
Research Abstract

In recent years, oligosaccharide-chains involved in complex glycoconjugates existing on a cell surface have attracted much attention of many researchers in various fields of biochemistry and organic chemistry. Therefore, in order to elucidate roles of oligosaccharide-chains, extensive studies have so far been carried out, and biologically very interesting results have been accumulated.
In the present study, carbohydrate-mimicking pseudo-oligosaccharides were designed and synthesized in order to provide chemical tools which may be useful to study roles of glycosidases and glycosyltransferases involved in biosynthesis of such complex oligosaccharide-chanins fo cell-surface glycanes. Several carba-disaccharides and trisaccharides containing carba-sugar residues bonded by way of imino-, ether and sulfide linkages have been newly synthesized and subjected to biological assay. In general, imino-linked carba-oligosaccharides were shown to possess inhibitory action against glycosidases, whereas the carba-oligosaccahrides linked by ether or sulfide-bridge were found to act rather as substrate analogs toward glycosyltransferases. The present results have opened up new opportunity for the design and synthesis of inhibitors for enzymes. Since carba-sugars are chemically very stable cyclitol derivstives but have close similarlity toward three-dimensional structures of true sugars, different kind of chemical modification may be possibly designed for carba-sugar residues.
The present studies have been collaborated with biochemistry professors, Drs.Hindsgaul and Palcic (University of Alberta, Canada), and our synthesized carbohydrate mimics of biological interests seem to assist and contribute to their extensive studies on sugar hydrolases and transferases for important oligosaccharide-chains in future.

Report

(4 results)
  • 1996 Annual Research Report   Final Research Report Summary
  • 1995 Annual Research Report
  • 1994 Annual Research Report
  • Research Products

    (20 results)

All Other

All Publications (20 results)

  • [Publications] S.Ogawa,N.Matsunaga,M.M.Palcic: "Synthesis of carbadisaccharides of biological interest:ether-linked octyl 5a′-carba-β-lactosaminide and related compounds" Carbohydrate Letters. (in press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Ogawa,K.Hirai,T.Yamazaki,A.Nakajima,N.Matsunaga: "Synthesis of methyl 5a′-carba-β-lactosides" Carbohydrate Letters. 183-188 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Ogawa,K.Hirai,M.Ohno,T.Furuya,S.Sasaki,H.Tsunoda: "Preparation of versatile intermediates for ether-linked 5a′-carbaoligosac-charides:synthesis of 5a-carba-β-D-GlcpNAc-(1→4)-D-Manp" Liebigs Annalen der Chemie. 673-677 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Tsunoda,S.Sasaki,T.Furuya,S.Ogawa: "Synthesis of methyl 5a′-carbamaltoses linked by imino,ether and sulfide bridges and unsaturaled derivatives thereof" Liebigs Annalen der Chemie. 159-165 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Ogawa,S.Sasaki,H.Tsunoda: "Synthesis of carbocyclic analogs of the mannosyl trisaccharide:ether and imino-linked methyl 3,6-bis(5a-carba-α-D-mannopyranosyl)-3,6-dideoxy-α-D-mannopyranosides" Carbohydrate Research. 274. 183-196 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Ogawa,T.Furuya,H.Tsunoda: "Synthesis of β-D-GlopNAc-(1→2)-5a-carba-α-D-Manp-(1→6)-β-D-Glcp-O(CH_2)_7CH_3" Carbohydrate Research. 271. 197-205 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Ogawa, K.Hirai, T.Yamazaki, A.Nakajima, N.Matsunaga: "Synthesis of methyl 5a'-carba-beta-lactosides" Carbohydrate Letters. 183-188 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Ogawa, K.Hirai, M.Ohno, T.Furuya, s.Sasaki, H.Tsunoda: "Preparation of versatile intermediates for ether-linked 5a'-carbaoligosaccharides" Liebigs Annalen der Chemie. 673-677 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Tsunoda, S.Sasaki, T.Furuya, S.Ogawa: "Synthesis of methyl 5a'-carbamaltoses linked by imino ether and sulfide bridges and unsaturated derivatives thereof" Liebigs Annalen der Chemie. 159-165 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Ogawa, S.Sasaki, T.Tsunoda: "Synthesis of carbocyclic analogs of the mannosy trisaccharide : eter-and imino-linked methyl 3,6-bis (5a-carba-alpha-D-mannopyranosyl)-3,6-dideoxy- -D-mannopyrano-sides" Carbohydrate Research. 274. 183-196 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Ogawa, T.Furuya, H.Tsunoda: "Synthesis of beta-D-GlcpNAc- (1*2) -5a-carba-alpha-D-Manp- (1*6) -beta-D-Glcp-o (CH_2)_7CH_3 : a reactive acceptor analog for Glc-NAc T-V" Carbohydrate Research. 271. 197-205 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Tsunoda,S.Sasaki,T.Furuya,S.Ogawa: "Synthesis of Methyl 5a′-Carbamaltoses Linked by Imino,Ether and Sulfide Bridges and Unsaturated Derivatives Thereof" Liebigs Annalen der Chemie. 159-165 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] S.Ogawa,K.Hirai,M.Ohno,T.Furuya,S.Sasaki,H.Tsunoda: "Preparation of Versatile Intermediates for Ether-Linked 5a-Carba Oligosaccharides:Synthesis of 5a-Carba-β-D-GlcpNAc-(1→4)-D-Manp" Liebigs Annalen der Chemie. 673-677 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] S.Ogawa,K.Hirai,T.Yamazaki,A.Nakajima,N.Matsunaga: "Synthesis of Methyl 5a′-Carba-β-lactosides" Carbohydrate Letters. 2. 183-188 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] S. Ogawa, T. Furuya, H. Tsunoda: "Synthesis of β-D-GlcpNAc- (1→2) 5a-carba-α-D-Manp- (1→6) -β-D-Glcp-O(CH_2) CH_3: A Reactive Acceptor Analog for GlcNAcT-V" Carbohydrate Research. 271. 197-205 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] S. Ogawa, S. Sasaki, H. Tsunoda: "Synthesis of Carbocyclic Analogs of the Mannosyl Trisaccharide: Ether- and Imino-Linked Methyl 3,6-bis (5a-carba-α-D-mannopyranosyl) -3,6-dideoxy-α-D-mannopyranosides" Carbohydrate Research. 274. 183-196 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] H. Tsunoda, S. Sasaki, T. Furuya, S. Ogawa: "Synthesis of Methyl 5a'-Carbamaltoses Linked by Imino, Ether and Sulfide Bridges and Unsaturated Derivatives Thereof" Liebigs Annalen der Chemie. 159-165 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] S.Ogawa,T.Furuya,H.Tsunoda: "Synthesis of β-D-GlcpNAc-(1→2)-5a-carba-α-D-Manp-(1→6)-β-D-Glcp-O(CH_2)_7CH_3:A Reactive Acceptor Analog for GlcNAcT-V" Carbohydrate Research in press(1995). (1995)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Ogawa,S.Sasaki,H.Tsunoda: "Synthesis of Carbocyclic Analogs of the Mannosyl Trisaccharide:Ether-and Imino-Linked Methyl 3,6-bis(5a-carba-α-D-mannopyranosyl)-3,6-dideoxy-α-D-mannopyranosides" Carbohydrate Research in press(1995). (1995)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Ogawa,Ed.Y.C.Lee and R.T.Lee: "Methods in Enzymology,Vol.247,Neoglycoonjugates Part B Biomedical Application" Academic Press,New York, 450 (1994)

    • Related Report
      1994 Annual Research Report

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Published: 1994-04-01   Modified: 2016-04-21  

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