A comparison of enzymatic hydrolysis and synthesis of optically active (4R)-2-methoxycarbonylmethyl-4-alkyloxy-2-cyclopentene-1-one using the Penicillium solitum lipase

I. Veinberga, J. Freimanis, H. Kazoka

Institute of Organic Synthesis, Latvian Academy of Sciences, Riga

Abstract: Enzymatic hydrolysis of (4R,S)-2-methoxycarbonylmethyl-4-hydroxy-2-cyclopen-tene-1-one esters and their enzymatic synthesis via direct esterification or transesterification in organic solvents in the presence of small amounts of water using lipase from Penicillium solitum was studied.

The structure of the esters acyl moiety (or) of carboxylic acids used for their synthesis and containing 2 to 18 carbon atoms affects the enantioselectivity of both hydrolysis and synthesis. Using vinyl acetate, the enantioselectivity of synthesis is twice as high as that of hydrolysis of the corresponding acetyl derivative. In both cases, the R-enantio-mer reacts faster. This enables one to raise the optical purity of (4R)-2-methoxycarbonyl-methyl-4-cyclopentene-1-one by alternating the reactions of enzymatic synthesis and hydrolysis.

Russian Journal of Bioorganic Chemistry 1991, 17 (6):760-766

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