Preparation of Sterically Demanding 2,2-Disubstituted-2-Hydroxy Acids by Enzymatic Hydrolysis
Articolo
Data di Pubblicazione:
2019
Citazione:
Preparation of Sterically Demanding 2,2-Disubstituted-2-Hydroxy Acids by Enzymatic Hydrolysis / A. Pinto, I. Serra, D. Romano, M.L. Contente, F.E. Molinari, F. Rancati, R. Mazzucato, L. Carzaniga. - In: CATALYSTS. - ISSN 2073-4344. - 9:2(2019 Feb). [10.3390/catal9020113]
Abstract:
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.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
esterase; stereoselective; ester hydrolysis; antimuscarinic agents; pig liver esterase (PLE)
Elenco autori:
A. Pinto, I. Serra, D. Romano, M.L. Contente, F.E. Molinari, F. Rancati, R. Mazzucato, L. Carzaniga
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