title: Enzymatic Kinetic Resolution of Secondary Alcohols Using an Ionic Anhydride Generated In Situ.
abstract: We developed a method for the resolution of secondary alcohols using an ionic anhydride acylating agent prepared directly in the reaction medium containing the biocatalyst Candida antarctica lipase B (CALB). NMR studies showed that mixing all components at the same time does not interfere with the coupling reaction or the enzymatic activity. After optimization of the reaction conditions, the method allowed the resolution of a number of substrates in very high conversions (46-48 %) and enantiomeric ratios (E>170) along with an easy recovery of both enantiomers without the need for preparative chromatographic separation. Additionally, both the starting ionic acid and the biocatalyst could be recovered and reused up to nine cycles without significant loss of enantioselectivity.
authors.affiliation: Institute for Bioengineering and Biosciences, Department of Bioengineering, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais 1, 1049-001, Lisboa, Portugal.
authors.forename: Ângelo
authors.initials: Â
authors.lastname: Rocha
authors.affiliation: Institute for Bioengineering and Biosciences, Department of Bioengineering, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais 1, 1049-001, Lisboa, Portugal.
authors.forename: Raquel
authors.initials: R
authors.lastname: Teixeira
authors.affiliation: Institute for Bioengineering and Biosciences, Department of Bioengineering, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais 1, 1049-001, Lisboa, Portugal.
authors.forename: Nuno M T
authors.initials: NM
authors.lastname: Lourenço
authors.affiliation: Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-009, Lisboa, Portugal.
authors.forename: Carlos A M
authors.identifier: http://orcid.org/0000-0002-7284-5948
authors.initials: CA
authors.lastname: Afonso
mesh_terms: D000215:Acylation; D000438:Alcohols / Q000737:chemistry*; D000812:Anhydrides / Q000737:chemistry*; D055162:Biocatalysis; D005656:Fungal Proteins / Q000378:metabolism*; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*
chemical_list: D000438:Alcohols; D000812:Anhydrides; D005656:Fungal Proteins; D008049:Lipase; C431349:lipase B, Candida antarctica
keywords: acid anhydrides; acylating agent; carbodiimides; ionic liquids; kinetic resolution