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Bio-synthesis and Function of a Novel Cross-linking Amio Acid, of Elastin Allodesmosine.

Research Project

Project/Area Number 02660293
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 Univ., Fac. Agric., Associate Prof., 農学部, 助教授 (70005635)

Co-Investigator(Kenkyū-buntansha) SUGAWARA Hiroshi  Tohoku Univ., Fac. Agric., Assistant, 農学部, 教務職員 (80089797)
Project Period (FY) 1990 – 1991
Project Status Completed (Fiscal Year 1991)
Budget Amount *help
¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1991: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1990: ¥1,300,000 (Direct Cost: ¥1,300,000)
KeywordsElastin / Cross-linking amino acid / Allodesmosine / Aldol Cross-link
Research Abstract

Elastin is a connective tissue protein found in virtually every tissue and organs. Elastin is primarily synthesized during physiological development by cells as a soluble precursor, tropoelastin. Tropoelastin are exposed to the extracellular space Ydierc. - they continue to undergo chemical modifications that result uLtimately in formation of specific kinds of covalent attachments, called cross-link. Ultimately, a family of different crosslinks restilts, many members of which have now have been isolated and identified.
A new pentafmotional cross-]Linking andno acid, termed allodesmosine, was isolated from bovine lige-mntum nuchae, aorta and lung elastin This was characterized by LAI, NMR and MS spectroscopy. The compound was shown by Uv and 1H-NMR to have pyridinium ring structure. Mass spectral analysis indicated a pELrent ural with a mass of 655. We postulated that it arose by condensation of a redurw aldol condensation products via aldol crogs-liriking amino acid, aldosine, which is novel amino acid isolated AM identified in this project by our laboratory.
In our model reaction, we employed the aldol corxiensation products of propanal, 2methyl-2-pentenal(MP), as aldehydes, and n-butylamine(l)and lysine(2)as primary amities. The reaction of MP and I and 2 was carried out under the neutral condition at room temperature. Hofmann degradation(160-170 ゚C for 10min)of water soltibl. e reactanlq gave various pyridines, 2-ethyl-, 4-etityl- and 2-(l-methyl-l-biitenyl)-3, 5-dimethylpyridine with other nuidetitLfied pyridines. From the reaction products of MP and 2, 1-alpha-aminoadipicaid 2-(l-mtyl-l-buLe-nyl.)-3, 5-dimetylpyridinium which was formffl by the condensation of 2 moles of MP and epsilon-amnino group of lysine was separated and identified. A highperforwmce liquid chromatgraphic procedxjlre for the determination of allodesmosine with other cross-links has been developed.

Report

(3 results)
  • 1991 Annual Research Report   Final Research Report Summary
  • 1990 Annual Research Report
  • Research Products

    (9 results)

All Other

All Publications (9 results)

  • [Publications] 須山 享三: "Isolation and Structural Identification of a New Crossーlinking Amino Acid,Allodesmosine,from the Acid Hydrolysate of Elastin" Agricultural and Biological Chemistry. 55. 547-554 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] 須山 享三: "動物体結合組織タンパク質の架橋構造と機能 ーとくにエラスチンの架橋についてー" 化学と生物. 29. 90-98 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] 中村 文彦,須山 享三: "Silica gel highーPerformance liguid chromatography of the determination of Crossーlinbs in elastin" Journal of Chromatographic Science. 29. 217-220 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] 中村 文彦,須山 享三: "牛項靭帯,大動脈および肺を素材としたピリジニウム環含有架橋アミノ酸の分離調製" 日本蓄産学会報. 62. 186-193 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] 須山 享三: "Aldosine,an Acid Hydrolysis Product from the Aldol Crossーlink of Bovine Elastin and Collagen" Agricultural and Biological Chemistry. 55. 3147-3149 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] 須山 享三: "Aldosine,a new amino acid derived from aldol crossーlinK of elastin and callagen" Proc.1st lntn.Cont.Amino Acid Res.,. (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] 須山 享三: "Isolation and Structual Identification of a New Crossーliking Amino Acid,Allodesmosine,from the Acid Hydrolysate of Elastin" AGRICULTURAL AND BIOLOGICAL CHEMISTRY. 55. 547-554 (1991)

    • Related Report
      1990 Annual Research Report
  • [Publications] 須山 享三: "3ー(2CARBOXYー6ーPIPERIDINYL)ー2,3,4,5ーTETRAHYDROー2ーPYRIDINECARBOXYLIC ACID,Aldosine:NOVEL ACID HYDROLYSIS PRODUCT OF BOVINE EAROTA ELASTIN" Biochem.Biophys.Res.Commun.

    • Related Report
      1990 Annual Research Report
  • [Publications] 須山 享三: "動物体結合組織タンパク質の架橋構造と機能" 化学と生物. 29. 90-98 (1991)

    • Related Report
      1990 Annual Research Report

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Published: 1990-04-01   Modified: 2016-04-21  

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