Pr(OTf) sub(3)-promoted Chichibabin pyridine synthesis of isodesmosine in H sub(2)O/MeOH

1,2,3,5-Tetrasubstituted pyridinium amino acid isodesmosine is a crosslinking amino acid of elastin and is an attractive biomarker for the diagnosis of chronic obstructive pulmonary disease (COPD). Herein, we report an application of the Chichibabin pyridine synthesis to the total synthesis of isode...

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Bibliographic Details
Published in:Tetrahedron letters 2014-11, Vol.55 (46), p.6343-6346
Main Authors: Sugimura, Takanori, Komatsu, Akira, Koseki, Yohei, Usuki, Toyonobu
Format: Article
Language:English
Subjects:
Amino acids
Biomarkers
Crosslinking
Diagnosis
Lysine
Pyridines
Synthesis (chemistry)
Tetrahedrons
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Summary:1,2,3,5-Tetrasubstituted pyridinium amino acid isodesmosine is a crosslinking amino acid of elastin and is an attractive biomarker for the diagnosis of chronic obstructive pulmonary disease (COPD). Herein, we report an application of the Chichibabin pyridine synthesis to the total synthesis of isodesmosine. Specifically, the appropriate protected lysine and the corresponding aldehyde were reacted using Pr(OTf) sub(3) in H sub(2)O/MeOH.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2014.09.097