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1993 Fiscal Year Final Research Report Summary

Studies on the function and biosynthesis of oxodesmosine, new cross-linking amino acid of elastin

Research Project

Project/Area Number 04660301
Research Category

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

Allocation TypeSingle-year Grants
Research Field 畜産化学
Research InstitutionTohoku University

Principal Investigator

SUYAMA Kyozo  Tohoku University, Faculty of Agriculture, Associate Professor, 農学部, 助教授 (70005635)

Co-Investigator(Kenkyū-buntansha) OHTOMO Yasushi  Tohoku University, Faculty of Agriculture, Research Technician, 農学部, 教務技官
Project Period (FY) 1992 – 1993
KeywordsOxodesmosine / Isooxodismosine / Elastin / Crosslink / Amino Acid / Desmosine
Research Abstract

Elastin is one of the connective tissue protain found in virtually every tissue and organs of mature animals and is major constituent of blood vessels and certain ligaments and other compliant tissues such as lung and skin. Elastin is primarily synthesized during physiological development by such cells as the vascular smooth muscle and fibroblast as a soluble precursor, tropoelastin. Several pairs of deaminated lysyl residues in each tropoelestin molecule are involved in a set of spontaneous condensation reactions that lead to the formation of crosslinking amino acids. In our experiments, we isolated two new crosslinking amino acids having N-substituted dihydrooxopyridine structure named oxodesmosine and isooxodesmosine from bovine aorta elastin. Both oxodesmosine and isooxodesmosine were very hygroscopic, white solid with faint yellow tinges, soluble in aqueous solvents. Structural analysis of both amino acids were done by UV, NMR and MS.It might be deduced from the structure of N-substituted dihydrooxopyridine skeleton that these new amino acids are metabolic intermediate of major pyridinium crosslinking amino acids, desmosine and isodesmosine. The in vivo synthesis of both amino acids were probably took place by oxydation of desmosine and isodesmosine as intermediate for further decompositions of such crosslinks. Although the mechanical details are not clear, one must invoke the cyclization, accompany with decarboxylation reaction during acid hydrolysis to form cyclopentene skeleton.

  • Research Products

    (11 results)

All Other

All Publications (11 results)

  • [Publications] 須山享三・中村文彦: "Two fluorescent crosslinking amino acid having N-substituted dihydroxopyridine skeleton isolated from bovine elastin" Bioorganic and Medicinal Chemistry. 2. 1767-1770 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 中村文彦・須山享三: "Isolation and characterization of a new crosslinking amino acid “Oxodesmosine" from Acid hydrolysate of elastin" Proceeding of the First International Coference of Amino Acid Research. 645-649 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 中村文彦・須山享三: "Two novel oxopyridine crosslinks of bovine elastin" Connective Tissue. 24. 127-128 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 須山享三・中村文彦: "HPLC of elastin crosslinking amino acid" Connective Tissue. 24. 125-126 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 中村文彦・須山享三: "Synthesis of anabasine-6'-carboxylic acid from aldosine the aldol crosslinking amino acid of elastin" Jounal of Chemical Society (London) Perkin transaction 1. 1993. 1007-1010 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 須山享三・梅田英幸: "Analysis of N-substituted dihydroxopyridine crosslinks “oxodesmosine" and “isoxodesmosine"." Analytical Biochemistry.

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Kyouzo Suyama and Fumihiko Nakamura: "Two Fluorescent Crosslinking Amino Acid Having N-Substituted Dihydrooxopyridine Skeleton Isolated From Bovine Elastin" Bioorg. Med. Chem. Lett.2. 1767-1770 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Fumihiko Nakamura and Kyozo Suyama: "Isolation and Characterization of a New Cross-linking Amino Acid "Oxodesmosine" from the Acid Hydrolysate of Elastin" Proc. 1st Intn. Conf. Amino Acid Res.645-649 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Fumihiko Nakamura and Kyozo Suyama: "Two Novel Oxopyridine Crosslinks of Bovine Aorta Elastin" Connec. Tissue. 24. 125-126 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Kyouzo Suyama and Fumihiko Nakamura: "HPLC of Elastin Crosslinking Amino Acids" Connec. Tissue. 24. 127-128 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Fumihiko Nakamura and Kyozo Suyama: "Synthesis of Anabasine-6'-carboxylic Acid from Aldosine, the Aldol Crosslinking Amino Acid of Elastin" J.Chem. Soc. (London) Parkin Trans.1. 1007-1010 (1993)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1995-03-27  

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