title: 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.
authors.affiliation: Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University , 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan.
authors.forename: Toyonobu
authors.initials: T
authors.lastname: Usuki
authors.forename: Takanori
authors.initials: T
authors.lastname: Sugimura
authors.forename: Akira
authors.initials: A
authors.lastname: Komatsu
authors.forename: Yohei
authors.initials: Y
authors.lastname: Koseki
mesh_terms: D015415:Biomarkers / Q000378:metabolism; D032701:Biomimetics; D003432:Cross-Linking Reagents / Q000737:chemistry; D003895:Desmosine / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004549:Elastin / Q000737:chemistry / Q000378:metabolism*; D006801:Humans; D007524:Isodesmosine / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D028581:Lanthanoid Series Elements / Q000737:chemistry; D015394:Molecular Structure; D029424:Pulmonary Disease, Chronic Obstructive / Q000378:metabolism*; D011725:Pyridines / Q000378:metabolism; D011726:Pyridinium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D015415:Biomarkers; D003432:Cross-Linking Reagents; D028581:Lanthanoid Series Elements; D011725:Pyridines; D011726:Pyridinium Compounds; D003895:Desmosine; D004549:Elastin; D007524:Isodesmosine; C023666:pyridine