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Enzymatic kinetic resolution of hydroxystearic acids: A combined experimental and molecular modelling investigation

EBERT, CYNTHIA
•
FELLUGA, FULVIA
•
FORZATO, Cristina
altro
L. Masotti
2012
  • journal article

Periodico
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC
Abstract
Enantioenriched 7-, 8-, 9-, and 10-hydroxystearic acids (HSA) were obtained, for the first time, by kinetic resolution of their racemates with lipases CALB and PS, in the presence of vinyl acetate. Among them, the best results were obtained for 7-HSA and 9-HSA, whose enantiomeric excess was around 55%. The same resolutions carried out on the hydroxy esters completely failed. For the acid substrates neither the Kazlauskas’ rule nor the 3D-QSAR model could be applied, since both models are focused on the CALB alcohol-pocket evaluation and not on the acyl-pocket one. Therefore, a semiquantitative approach was used, whose results were in accordance with our findings, as far as the absolute configuration of the product is concerned.
DOI
10.1016/j.molcatb.2012.06.017
WOS
WOS:000309294100006
SCOPUS
2-s2.0-84864507988
Archivio
http://hdl.handle.net/11368/2578820
http://dx.doi.org/10.1016/j.molcatb.2012.06.017
Diritti
metadata only access
Soggetti
  • Hydroxystearic acids

  • Enzymatic resolution

  • CALB

  • Molecular recognition...

Web of Science© citazioni
15
Data di acquisizione
Jun 9, 2022
Scopus© citazioni
17
Data di acquisizione
Jun 15, 2022
Vedi dettagli
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