[(13)C3,(15)N1]-labeled isodesmosine: A potential internal standard for LC-MS/MS analysis of desmosines in elastin degradation

Takahiro Tanigawa; Akira Komatsu; Toyonobu Usuki

doi:10.1016/j.bmcl.2015.03.084

[(13)C3,(15)N1]-labeled isodesmosine: A potential internal standard for LC-MS/MS analysis of desmosines in elastin degradation

Bioorg Med Chem Lett. 2015;25(10):2046-9. doi: 10.1016/j.bmcl.2015.03.084. Epub 2015 Apr 3.

Authors

Takahiro Tanigawa¹, Akira Komatsu¹, Toyonobu Usuki²

Affiliations

¹ Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan.
² Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan. Electronic address: t-usuki@sophia.ac.jp.

PMID: 25890800
DOI: 10.1016/j.bmcl.2015.03.084

Abstract

Isodesmosine and desmosine are crosslinking amino acids that are present only in elastin. They are useful biomarkers for the degradation of elastin, which occurs during the progression of chronic obstructive pulmonary disease (COPD) and related diseases. This Letter describes the synthesis of [(13)C3,(15)N1]-labeled isodesmosine, using Chichibabin pyridine synthesis as a key reaction. The labeled isodesmosine is a potential internal standard for the quantitative LC-MS/MS analysis of desmosines in elastin degradation.

Keywords: Biomarker; Chichibabin pyridine synthesis; Elastin degradation; Isodesmosine; Isotopic label.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Biomarkers / metabolism
Carbon Isotopes / analysis
Chromatography, Liquid*
Desmosine / analysis*
Elastin / chemistry
Elastin / metabolism*
Isodesmosine / chemical synthesis*
Isodesmosine / chemistry
Molecular Structure
Nitrogen Isotopes / analysis
Pulmonary Disease, Chronic Obstructive / pathology
Tandem Mass Spectrometry*

Substances

Biomarkers
Carbon Isotopes
Nitrogen Isotopes
Desmosine
Elastin
Isodesmosine