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20.2.1.2.10.1.7 Enzymatic Hydrolysis

DOI: 10.1055/sos-SD-120-00030

Mourad, A. K.; Czekelius, C.Science of Synthesis Knowledge Updates, (2011365.

A variety of structurally diverse esters can be hydrolyzed in aqueous media or suitable organic solvents using enzymes which are isolated from natural sources.[‌46‌,‌47‌] For high efficiency in ester hydrolysis, enzymes with an appropriate substrate scope have to be selected or screened. If suitable enzymes are chosen, highly stereoselective transformations, including desymmetrizations, are possible.[‌48‌,‌49‌] In addition, enzyme-catalyzed hydrolysis can be combined with in situ racemization of the ester starting material.[‌50‌] Improvements to the method have included specific enzyme engineering, immobilization, and derivatization.[‌46‌] Examples include the use of pig liver esterase to convert meso-diester 21 into (R)-5-methoxy-3-methyl-5-oxopentanoic acid (22), and the transformation of racemic ethyl ester 23 into chiral (S)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid (24) using Streptomyces griseus protease (Table 6).

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