IsoChichibabin desmosine-C,N synthesis and quantitative LC-MS/MS analysis of desmosine and isodesmosine in human skin.

Bioorg Med Chem

Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan. Electronic address:

Published: December 2021

AI Article Synopsis

  • Desmosine and isodesmosine are important crosslinking amino acids in elastin, which is crucial for the structure of skin.
  • Previous attempts to measure these crosslinkers in human skin have struggled due to the insoluble nature of elastin proteins.
  • This study successfully synthesized isotopically labeled desmosine and used advanced analysis techniques to quantitatively measure desmosine levels in human skin for the first time, detecting approximately 1.43 μg from 1 mg of dry skin.

Article Abstract

Desmosine and isodesmosine are crosslinking amino acids of elastin, which is an essential component of the dermal extracellular matrix protein. Quantitative analysis of crosslinker desmosines in human skin dermis has not been fully achieved due to the insoluble nature of elastin protein. In the present study, chemical synthesis of isotopically labeled desmosine, desmosine-C,N, was carried out via isoChichibabin pyridinium synthesis starting from corresponding isotopically labeled amino acids. Isotope-dilution LC-MS/MS analysis of desmosine and isodesmosine utilizing synthetic desmosine-C,N enabled the quantitative analysis of desmosines in human skin for the first time. Thus, ca. 1.43 μg of desmosines was detected from analysis of 1 mg of dry human skin.

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Source
http://dx.doi.org/10.1016/j.bmc.2021.116519DOI Listing

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