Biomimetic Chichibabin Pyridine Synthesis of the COPD Biomarkers and Elastin Cross-Linkers Isodesmosine and Desmosine

Abstract

The tetrasubstituted pyridinium amino acids isodesmosine and desmosine are cross-linkers of elastin and are attractive biomarkers for the diagnosis of chronic obstructive pulmonary disease (COPD). In this study, the biomimetic total synthesis of isodesmosine and desmosine via a lanthanide-promoted Chichibabin pyridine synthesis using the corresponding aldehyde and amine hydrochloride is reported.