title: Impact of the configuration of a chiral, activating carrier on the enantioselectivity of entrapped lipase from Candida rugosa in cyclohexane.
abstract: Lipase from Candida rugosa was loaded into an amphiphilic polymer co-network (APCN) composed of the chiral poly[(R)-N-(1-hydroxybutan-2-yl) acrylamide] [P-(R)-HBA] and P-(S)-HBA, respectively, linked by poly(dimethylsiloxane). The nanophase-separated amphiphilic morphology affords a 38,000-fold activation of the enzyme in the esterification of 1-phenylethanol with vinyl acetate. Further, the enantioselectivity of the entrapped lipase was influenced by the configuration of the chiral, hydrophilic polymer matrix. While the APCN with the (S)-configuration of the APCN affords 5.4 faster conversion of the (R)-phenylethanol compared to the respective (S)-enantiomer, the (R)-APCN allows an only a 2.8 faster conversion of the (R)-enantiomer of the alcohol. Permeation-experiments reveal that the enantioselectivity of the reaction is at least partially caused by specific interactions between the substrates and the APCN.
authors.affiliation: Freiburg Material Research Center and Institute for Macromolecular Chemistry, University of Freiburg, Stefan-Meier-Str. 21, 79104, Freiburg, Germany.
authors.forename: Jan
authors.initials: J
authors.lastname: Tobis
authors.forename: Joerg C
authors.initials: JC
authors.lastname: Tiller
mesh_terms: D001592:Benzyl Alcohols / Q000737:chemistry; D055162:Biocatalysis; D002175:Candida / Q000201:enzymology*; D003510:Cyclohexanes / Q000737:chemistry*; D004129:Dimethylpolysiloxanes / Q000737:chemistry; D004800:Enzymes, Immobilized / Q000378:metabolism*; D004951:Esterification; D008049:Lipase / Q000378:metabolism*; D011108:Polymers / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
chemical_list: D001592:Benzyl Alcohols; D003510:Cyclohexanes; D004129:Dimethylpolysiloxanes; D004800:Enzymes, Immobilized; D011108:Polymers; D014753:Vinyl Compounds; C506365:Cyclohexane; C002017:methylphenyl carbinol; D008049:Lipase; C011566:vinyl acetate