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Article

Preparation of Sterically Demanding 2,2-Disubstituted-2-Hydroxy Acids by Enzymatic Hydrolysis

1
Department of Food, Environmental and Nutritional Science (DeFENS), University of Milan, 20133 Milan, Italy
2
Chemistry Research and Drug Design Department, Corporate Preclinical R&D, Chiesi Farmaceutici S.p.A., 43122 Parma, Italy
*
Authors to whom correspondence should be addressed.
Catalysts 2019, 9(2), 113; https://doi.org/10.3390/catal9020113
Received: 18 December 2018 / Revised: 14 January 2019 / Accepted: 19 January 2019 / Published: 24 January 2019
Preparation of optically-pure derivatives of 2-hydroxy-2-(3-hydroxyphenyl)-2-phenylacetic acid of general structure 2 was accomplished by enzymatic hydrolysis of the correspondent esters. A screening with commercial hydrolases using the methyl ester of 2-hydroxy-2-(3-hydroxyphenyl)-2-phenylacetic acid (1a) showed that crude pig liver esterase (PLE) was the only preparation with catalytic activity. Low enantioselectivity was observed with substrates 1a–d, whereas PLE-catalysed hydrolysis of 1e proceeded with good enantioselectivity (E = 28), after optimization. Enhancement of the enantioselectivity was obtained by chemical re-esterification of enantiomerically enriched 2e, followed by sequential enzymatic hydrolysis with PLE. The preparation of optically-pure (S)-2e was validated on multi-milligram scale. View Full-Text
Keywords: esterase; stereoselective; ester hydrolysis; antimuscarinic agents; pig liver esterase (PLE) esterase; stereoselective; ester hydrolysis; antimuscarinic agents; pig liver esterase (PLE)
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MDPI and ACS Style

Pinto, A.; Serra, I.; Romano, D.; Contente, M.L.; Molinari, F.; Rancati, F.; Mazzucato, R.; Carzaniga, L. Preparation of Sterically Demanding 2,2-Disubstituted-2-Hydroxy Acids by Enzymatic Hydrolysis. Catalysts 2019, 9, 113. https://doi.org/10.3390/catal9020113

AMA Style

Pinto A, Serra I, Romano D, Contente ML, Molinari F, Rancati F, Mazzucato R, Carzaniga L. Preparation of Sterically Demanding 2,2-Disubstituted-2-Hydroxy Acids by Enzymatic Hydrolysis. Catalysts. 2019; 9(2):113. https://doi.org/10.3390/catal9020113

Chicago/Turabian Style

Pinto, Andrea, Immacolata Serra, Diego Romano, Martina L. Contente, Francesco Molinari, Fabio Rancati, Roberta Mazzucato, and Laura Carzaniga. 2019. "Preparation of Sterically Demanding 2,2-Disubstituted-2-Hydroxy Acids by Enzymatic Hydrolysis" Catalysts 9, no. 2: 113. https://doi.org/10.3390/catal9020113

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