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Synthesis of Multi‐Deuterated Desmosine
Author(s) -
Hirose Mika,
Yokoo Reiko,
Watanabe Daisuke,
Suzuki Rina,
Tanigawa Miho,
Usuki Toyonobu
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202000507
Subject(s) - desmosine , chemistry , elastin , isotope dilution , sonogashira coupling , chromatography , organic chemistry , mass spectrometry , amino acid , biochemistry , medicine , palladium , pathology , catalysis
Desmosine, a crosslinking pyridinium amino acid found in elastin, is a useful biomarker for the diagnosis of diseases related to elastin degradation, such as chronic obstructive pulmonary disease (COPD). In order to achieve the precise quantitation of this compound using isotope dilution liquid chromatography‐tandem mass spectrometry (LC‐MS/MS) analysis, isotopically‐labeled internal standards including deuterated desmosine are required. We report herein the synthesis of multi‐deuterated desmosine (d 3–9 ) as a potential internal standard. This synthesis involves the preparation of an alkyne via a Sonogashira cross‐coupling, followed by deuterogenation of the triple bond to incorporate deuterium atoms into the substrate.