Highly regioselective enzymatic synthesis of polymerizable derivatives of methyl shikimate

Regiocontrollable selectivity of enzymatic method for synthesis of polymerizable derivatives of methyl shikimate was described. Lipase acrylic resin from Candida antarctica (CAL-B) and immobilized lipase from Mucor miehei (MML) showed high regioselectivity toward the secondary hydroxyl of methyl shikimate, which presents three hydroxyl groups with similar reactivity. Catalysis by MML in acetone facilitated the single step synthesis of 5-O-acyl methyl shikimate derivatives in high yields, while the use of CAL-B in acetone afforded 4-O-acyl methyl shikimate derivatives. The obtained series of methyl shikimate derivatives would be important monomers for potential useful analogues of shikimic acid.

Graphical abstractRegiocontrollable selectivity of enzymatic method for synthesis of polymerizable derivatives of methyl shikimate was described. The obtained derivatives would be useful as important monomers for potential analogues of shikimic acid.Figure optionsDownload full-size imageDownload as PowerPoint slide