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Highly Regioselective Enzymatic Synthesis of Polymerizable Derivatives of Methyl Shikimate

Chao Li, Hai-Yang Wang, Na Wang, Yu-Guo Fang, Xi Chen, Xiao-Qi Yu

Bioorg Med Chem Lett. 2007 Dec 15;17(24):6687-90.

PMID: 17976984

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP9001621-C Lipase acrylic resin Lipase acrylic resin 9001-62-1 Price
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