Abstract
Co-embedding of an amphiphilic non-chiral hydrolysis catalyst with amphiphilic chiral additives into the membrane of a phospholipid vesicle induces different rates of ester hydrolysis for enantiomeric amino acid esters.
Highlights
View Article OnlineEnantioselective ester hydrolysis by an achiral catalyst co-embedded with chiral amphiphiles into a vesicle membrane†
Co-embedding of an amphiphilic non-chiral hydrolysis catalyst with amphiphilic chiral additives into the membrane of a phospholipid vesicle induces different rates of ester hydrolysis for enantiomeric amino acid esters
We report here the hydrolysis of enantiomeric amino acid esters on the modi ed surface of phospholipid vesicles (Fig. 1)
Summary
Enantioselective ester hydrolysis by an achiral catalyst co-embedded with chiral amphiphiles into a vesicle membrane†. Co-embedding of an amphiphilic non-chiral hydrolysis catalyst with amphiphilic chiral additives into the membrane of a phospholipid vesicle induces different rates of ester hydrolysis for enantiomeric amino acid esters. We report here the hydrolysis of enantiomeric amino acid esters on the modi ed surface of phospholipid vesicles (Fig. 1). A chiral, catalytically inactive membrane additive is coembedded with a catalytically active achiral metal complex Zn2Cy into the phospholipid membrane.[12,16] The membrane serves as two-dimensional platform with higher concentration of the amphiphilic membrane additives compared to the bulk solution.[17] This proximity of the chiral additive to the achiral metal complex affects its selectivity in ester hydrolysis and induces thereby different reaction rates for both enantiomers. Compounds PN-C12-Phe and PN-C2-Phe with a protected amino-group were prepared, which are stable in the absence of the hydrolysis catalyst
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