Total synthesis of collagen crosslinker deoxypyridinoline

Abstract

Collagen, a fibrous protein, accounts for 30 % of all proteins in the human body and serves as an essential extracellular matrix component that imparts mechanical strength to connective tissues such as skin and bones. Deoxypyridinoline, a collagen crosslinking amino acid, was first isolated from bovine bone in 1982. This compound is released into the bloodstream during bone resorption without being reused and has recently garnered attention as a biomarker for osteoporosis. In this study, we achieved the total synthesis of deoxypyridinoline, with a 22 % overall yield, in five steps from commercially available protected amino acids. The synthesis would aid a quantitative analysis of deoxypyridinoline as an alternative to isolating it from natural sources.