Enantioselective resolution of side-chain modified gem-difluorinated alcohols catalysed by Candida antarctica lipase B and monitored by capillary electrophoresis

0511157 - FZÚ 2020 RIV GB eng J - Journal Article
Pomeisl, Karel - Lamatová, N. - Šolínová, V. - Pohl, R. - Brabcová, J. - Kašička, V. - Krečmerová, M.
Enantioselective resolution of side-chain modified gem-difluorinated alcohols catalysed by Candida antarctica lipase B and monitored by capillary electrophoresis.
Bioorganic & Medicinal Chemistry. Roč. 27, č. 7 (2019), s. 1246-1253. ISSN 0968-0896. E-ISSN 1464-3391
Institutional support: RVO:68378271
Keywords : acyclic nucleoside phosphonates * candida antarctica lipase * capillary electrophoresis * enantioselective resolution * enzyme catalysis
OECD category: Biochemistry and molecular biology
Impact factor: 3.073, year: 2019
Method of publishing: Limited access
https://doi.org/10.1016/j.bmc.2019.02.022

An enzymatic alternative to the chemical synthesis of chiral gem-difluorinated alcohols has been developed. The method is highly effective and stereoselective, feasible at laboratory temperature, avoiding the use of toxic heavy metal catalysts which is an important benefit in medicinal chemistry including the synthesis of drugs and drug precursors. Candida antarctica lipases A and B were applied for the enantioselective resolution of side-chain modified gem-difluorinated alcohols,(R)-and(S)-3-benzyloxy-1,1-difluoropropan-2-ols, compounds serving as chiral building blocks in the synthesis of various bioactive molecules bearing a gem-difluorinated grouping. The catalytic activity of these lipases was investigated for the chiral acetylation in nonpolar solvents using vinylacetate as an acetyl donor.The dependence of the reaction course on various substrate and enzyme concentrations, reaction time, and temperature was monitored by chiral capillary electrophoresis (CE).
Permanent Link: http://hdl.handle.net/11104/0301493