Synthesis and LC-MS/MS Analysis of Cyclic Desmosien Peptides

2022 Fiscal Year Final Research Report

• Project/Area Number: 20K05734
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Review Section: Basic Section 37020:Chemistry and chemical methodology of biomolecules-related
• Research Institution: Sophia University
• Principal Investigator: USUKI Toyonobu 上智大学, 理工学部, 教授 (50514535)
• Project Period (FY): 2020-04-01 – 2023-03-31
• Keywords: エラスチン / desmosine / 環状ペプチド / LC-MS/MS

Outline of Final Research Achievements

Stepwise Sonogashira and Negishi cross-coupling reactions of trisubstituted halopyridines and the corresponding amino acid wih protecting groups were carried out. Cyclic peptides were prepared via intramolecular condensation of the peptide with three alanines. Furthermore, we succeeded in constructing a second cyclic peptide consisting of two alanines and one serine by cross-coupling and condensation reactions.
By LC-MS/MS analysis of the synthesized cyclic desmosine peptide, we confirmed the retention time on LC and the fragment pattern of MS/MS in detail. As a result of the analysis, we were able to identify the structure of the peptide chain at the cross-linking portion of elastin.

Free Research Field

エラスチン化学

Academic Significance and Societal Importance of the Research Achievements

エラスチンの架橋ペプチド構造は長年謎であったため、本研究成果は学術的に意義深い。エラスチン分解ペプチドは、エラスチン分解に関わる疾患のバイオマーカーになり得るため、間接的に社会的意義も大きいと考えられる。