1991 Fiscal Year Final Research Report Summary
Bio-synthesis and Function of a Novel Cross-linking Amio Acid, of Elastin Allodesmosine.
| Project/Area Number |
02660293
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
畜産化学
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| Research Institution | Tohoku University |
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Principal Investigator |
SUYAMA Kyozo Tohoku Univ., Fac. Agric., Associate Prof., 農学部, 助教授 (70005635)
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| Co-Investigator(Kenkyū-buntansha) |
SUGAWARA Hiroshi Tohoku Univ., Fac. Agric., Assistant, 農学部, 教務職員 (80089797)
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| Project Period (FY) |
1990 – 1991
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| Keywords | Elastin / Cross-linking amino acid / Allodesmosine / Aldol Cross-link |
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| 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.
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