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DOI: 10.1055/a-2205-7105
Synthesis of Ser-Ala-Ala Cyclic Desmosine
This work was supported in part by JSPS KAKENHI (grant nos. 19KK0420 and 20K05734).
Abstract
Elastin is present in the extracellular matrix of various tissues, most abundantly in the aorta and major vascular vessels, and is formed by self-assembly followed by concomitant crosslinkers of tropoelastin, an elastin precursor. Desmosine is a pyridinium-based tetrafunctional amino acid that serves as an important crosslinker to bind the polymeric chains of peptides in the 3D network of elastin. Despite its significance, the detailed structure of elastin has not been elucidated. In this work, the synthesis of a cyclic desmosine peptide designed to mimic elastin, which could serve as a compound for mass spectrometric analysis to elucidate crosslinking structures is reported. The synthesis involved stepwise and regioselective palladium-catalyzed cross-couplings, and inter- and intramolecular condensations.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2205-7105.
- Supporting Information
Publication History
Received: 01 October 2023
Accepted after revision: 07 November 2023
Accepted Manuscript online:
07 November 2023
Article published online:
13 December 2023
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