(2S,3R)-3-Hydroxyproline is a stereoisomer of hydroxyproline, a hydroxylated derivative of the amino acid proline. Structurally, it features a hydroxyl group (-OH) at the 3-position of the pyrrolidine ring, with specific stereochemistry at the 2nd and 3rd carbon atoms—(2S,3R)—which distinguishes it from other isomers like trans-4-hydroxyproline, a major component of collagen.
This compound is of particular interest in biochemical and pharmaceutical research due to its role as a building block in the synthesis of peptides and proteins with enhanced stability and bioactivity. (2S,3R)-3-Hydroxyproline may influence protein folding and resistance to enzymatic degradation, making it valuable in the design of collagen mimetics and therapeutic peptides. It is also used in studies related to fibrosis, tissue engineering, and the development of biomaterials. Its stereochemistry plays a critical role in its biological function and interaction with enzymes like prolyl hydroxylases.
Commercially, (2S,3R)-3-Hydroxyproline can be produced through enzymatic synthesis, chemical hydroxylation of proline, or fermentation using genetically engineered microbial strains.