Total synthesis of merodesmosine. (28th September 2022)

• Record Type: Journal Article
• Authors: Oishi, Kaho; Tanaka, Nao; Usuki, Toyonobu
• Is Part Of: Tetrahedron letters. Volume 107(2022)
• Publication Date: 2022-09-28
• Subjects: Total synthesis -- Amino acids -- Merodesmosine -- Elastin; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.154106
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Elastin is an important extracellular matrix protein responsible for the elasticity of tissues such as ligamentum, arteries, and lungs. Its three-dimensional crosslinking structure plays an important role in its elasticity. However, the precise structure has not yet been clarified since it is difficult to analyze due to its insoluble nature. Merodesmosine is one of the possible crosslinking amino acids in elastin. In this work, the first total synthesis of merodesmosine was achieved in five steps in 21% overall yield from protected allysine. This achievement will aid in the elucidation of the crosslinking structure of elastin.