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Studies on glycan processing inhibitors

Research Project

Project/Area Number 63560123
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field 製造化学・食品
Research InstitutionGifu University

Principal Investigator

KISO Makoto  Gifu University, Associate Professor, 農学部, 助教授 (90092931)

Co-Investigator(Kenkyū-buntansha) ISHIDA Hideharu  Gifu University, Assistant, 農学部, 助手 (20203002)
HASEGAWA Akira  Gifu University, Professor, 農学部, 教授 (10026429)
Project Period (FY) 1988 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1989: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1988: ¥1,400,000 (Direct Cost: ¥1,400,000)
KeywordsN-acetylneuraminic acid / KDO / 1-deoxynojirimycin / complex carbohydrates / glycan processing / KDO誘導体
Research Abstract

1. The 2-beta-SNa derivative of N-acetylneuraminic acid (Neu5Ac) was combined with cytidine, deoxycytidine and arabinosyl,cytosine, respectively, through the spacer-arms such as (a) -SCH_2O- and (b) -SCH_2CONH-, to give the corresponding CMP-Neu5Ac derivatives and analogs. These compounds showed the inhibition activity against Neu5Ac synthase and Neu5Ac transferase, and might be useful to analyze the biological functions of cell-surface sialo-glycoconjugates. The 2-beta-SNa derivative of 2-keto-3-deoxy-octonic acid (KDO) has, also been synthesized and combined with cytidine, deoxycytidine and arabinosyl cytosine, respectively, as described for Neu5Ac. The biological activities are now in investigation.
2.1-Deoxynojirimycin (DNJ) was converted, via the epoxide intermediates, into a series of N-acetylhexosamine analogs, i. e., 2-acetamido-1,2,5-trideoxy-1,5-imino- D-glucitol (GlcNAcDNJ), -D-mannitol (ManNAcDNJ), -D-galactitol (GalNAcDNJ) and their isomers. The inhibition activity against the corresponding N-acetylhexosaminidase was examines. GlcNAcDNJ was further converted to the disaccharides related to lactose, lactosamine and chitobiose which are the prominent components of widespread glycoconjugates. More complex glycans containing DNJ as a reducing-end component will be designed.

Report

(3 results)
  • 1989 Annual Research Report   Final Research Report Summary
  • 1988 Annual Research Report
  • Research Products

    (40 results)

All Other

All Publications (40 results)

  • [Publications] Kiso,M.: "Conjugates of biologically active lipid A-subunit analogs with 3-deoxy-D-manno-2-octulosonic acid(KDO)and its methyl ester." Carbohydr.Res.177. 51-67 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kanie,O.: "Glycosylation using methylthioglycosides of N-acetylneuraminic acid and dimethyl(methylthio)sulfonium triflate." J.Carbohydr.Chem.7. 501-506 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Murase,T.: "A facile regio-and stereo-selective synthesis of α-glycosides of N-acetylneuraminic acid" Carbohydr.Res.184. c1-c4 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Hasegawa,A.: "Synthetic studies on sialoglycoconjugates 4:synthesis of 5-acetamido-3,5-dideoxy-D-galacto-2-octulosonic acid derivatives and analogs." J.Carbohydr.Chem.8. 135-144 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kartha,K.P.R.: "Synthetic studyies toward gangliosides and their analogs;synthesis of appropriately protected core oligosaccharides ad construction blocks." J.Carbohydr.Chem.8. 145-158 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kartha,K.P.R.: "A facile,regio-and stereo-selective synthesis of ganglioside GM_3." Carbohydr.Res.188. 71-80 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kartha,K.P.R.: "Synthetic studyies on sialoglycoconjugates 9:an efficient method for the selective acetolysis of 2-(trimethylsilyl)ethyl glycosides using ferric chloride in acetic anhydride." J.Carbohydr.Chem.8. 675-679 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Murase,T.: "Synthetic studies on sialoglycoconjugates 10:facile 6-0-sialylation following stannylene activation of an unprotected D-galactopyranoside." Carbohydr.Res.195. 134-137 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 石田秀治: "シアル酸含有糖鎖の合成" 日本農芸化学会誌. 63. 1248-1252 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 木曾真: "含硫シアル酸誘導体" 生体の科学. 40. 518-519 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kiso,M.: "Synthesis of α-Kdo-(2-4-)-Kdo disaccharide derivatives and their conjugation with a protected form of GLA-60,a biologically active analog of a lipid A subunit." Carbohydr.Res.196. 59-73 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kiso,M.: "Studies on glycan processing inhibitors:synthesis of N-acetylhexosamine analogs of 1-deoxy-nojirimycin." J.Carbohydr.Chem.(1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 石田秀治: "複合糖質の化学と応用" シ-エムシ-, 14 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kiso, M., Fujita, M., Tanahashi, M., Fujishima, Y., Ogawa, Y., Hasegawa, A. & Unger F. M.: "Conjugates of biologically active lipid A-subunit analogs with 3-deoxy-D-manno-2-octulosonic acid (KDO) and its methyl ester." Carbohydr. Res. 177: 51-67, 1988.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kanie, O., Kiso, M. & Hasegawa, A.: "Glycosylation using methylthioglycosides of N-acetylneuraminic acid and dimethyl(methylthio)sulfonium triflate." J. Carbohydr. Chem. 7: 501-506, 1988.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Murase, T., Ishida, H., Kiso, M. & Hasegawa, A.: "A facile regio- and stereo-selective synthesis of alpha-glycosides of N-acetylneuraminic acid." Carbohydr. Res. 184: c1-c4, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Hasegawa, A., Ito, Y., Morita, M., Ishida, H. & Kiso, M.: "Synthetic studies on sialoglycoconjugates 4: synthesis of 5-acetamido-3,5-dideoxy-D-galacto-2-octulosonic acid derivatives and analogs." J. Carbohydr. Chem. 8: 135-144, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kartha, K. P. R., Kameyama, A., Kiso, M. & Hasegawa, A.: "Synthetic studies toward gangliosides and their analogs: synthesis of appropriately protected core oligosaccharides as construction blocks." J. Carbohydr. Chem. 8: 145-158, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Murase, T., Kartha, K. P. R., Kiso, M. & Hasegawa, A.: "Synthetic studies on sialoglycoconjugates 10: facile 6-O-sialylation following stannylene activation of an unprotected D-galactopyranoside." Carbohydr. Res. 195: 134-137, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kiso, M., Fujita, M., Ogawa, Y., Ishida, H. & Hasegawa, A.: "Synthesis of alpha-Kdo-(2->4)-Kdo disaccharide derivatives and their conjugation with a protected form of GLA-60, a biologically active analog of a lipid A subunit." Carbohydr. Res. 196: 1990.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kiso, M., Kitagawa M., Ishida, H. & Hasegawa, A.: "Studies on glycan processing inhibitors: synthesis of N-acetylhexosamine analogs of 1-deoxy-nojirimycin." J. Carbohydr. Chem.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kiso、M.: "Conjugates of biologically active lipid A-subunit analogs with 3-deoxy-D-manno-2-octulosonic acid(KDO)and its methyl ester." Carbohydr.Res.177. 51-67 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kanie、O.: "Glycosylation using methylthioglycosides of N-acetylneuraminic acid and dimethyl(methylthio)sulfonium triflate." J.Carbohydr.Chem.7. 501-506 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] Murase、T.: "A facile regio-and stereo-selective synthesis of α-glycosides of N-acetylneuraminic acid." Carbohydr.Res.184. c1-c4 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] Hasegawa、A.: "Synthetic studies on sialoglycoconjugates 4:synthesis of 5-acetamido-3、5-dideoxy-D-galacto-2-octulosonic acid derivatives and analogs." J.Carbohydr.Chem.8. 135-144 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kartha、K.P.R.: "Synthetic studies toward gangliosides and their analogs;synthesis of appropriately protected core oligosaccharides ad construction blocks." J.Carbohydr.Chem.8. 145-158 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kartha、K.P.R.: "A facile、regio-and stereo-selective synthesis of glycoside GM3." Carbohydr.Res.188. 71-80 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kartha、K.P.R.: "Synthetic studies sialoglycoconjugates 9:an efficient method for the selective acetolysis of 2-(trimethylslyl)ethyl glycosides using ferric chloride in acetic anhydride." J.Carbohydr.Chem.8. 675-679 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Murase、T.: "Synthetic studies on sialoglycoconjugates 10:facile 6-0-sialyiation following stannylene activation of an unprotected D-galactopyranoside." Carbohydr.Res.195. 134-137 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 石田秀治: "シアル酸含有糖鎖の合成" 日本農芸化学会誌. 63. 1248-1252 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 木曽真: "合成シアル酸誘導体" 生体の科学. 40. 518-519 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kiso、M.: "Synthesis of α-Kdo-(2-4)-Kdo disaccharide derivatives and their conjugation with a protected from of GLA-60、abiologically active analog of a lipid A subunit." Carbohydr.Res.196. 59-73 (1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kiso、M.: "Studeies on glycan processing inhibitors:synthesis of N-acetylthxosamine analogs of 1-deoxy-nojirimycin." J.Carbohydr.Chem.(1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] 石田秀治: "複合糖質の化学と応用" シ-エムシ-, 14 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Makoto,Kiso: Carbohydr.Res.177. 51-67 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Osamu,Kanie: J.Carbohydr.Chem.7(2). 501-506 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] K.P.R.Kartha: J.Carbohydr.Chem.8(1). (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] Makoto,Kiso: Carbohydr.Res.

    • Related Report
      1988 Annual Research Report
  • [Publications] Takatoshi,Murase: J.Carbohydr.Chem.

    • Related Report
      1988 Annual Research Report
  • [Publications] Makoto,Kiso: J.Carbohydr.Chem.

    • Related Report
      1988 Annual Research Report

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Published: 1988-04-01   Modified: 2016-04-21  

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