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Short Paper | Regular issue | Vol 104, No. 5, 2022, pp.961-968
Published online, 22nd February, 2022
DOI: 10.3987/COM-22-14620
Middle-Scale IsoChichibabin Desmosine Synthesis

Takahiro Suzuki, Nao Tanaka, Hiroaki Tanaka, and Toyonobu Usuki*

*Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan


Desmosine is a 1,3,4,5-tetrasubstituted pyridinium amino acid that crosslinks elastin, and is considered to be a useful biomarker for elastin-degraded diseases such as chronic obstructive pulmonary disease (COPD). In this work, starting from the corresponding aldehyde and amine, the isoChichibabin pyridinium synthesis of protected desmosine was achieved on a middle-scale in H2O/CH2Cl2 (1/6) with Pr(OTf)3. A shorter route for the synthesis of the aldehyde was also developed.