| Title : Stereoselectivity-Tailored, Metal-Free Hydrolytic Dynamic Kinetic Resolution of Morita-Baylis-Hillman Acetates Using an Engineered Lipase-Organic Base Cocatalyst - Xia_2017_ACS.Catal_7_4542 |
| Author(s) : Xia B , Xu J , Xiang Z , Cen Y , Hu Y , Lin X , Wu Q |
| Ref : ACS Catal , 7 :4542 , 2017 |
| Abstract : Metal-free enantiocomplementary hydrolytic dynamic kinetic resolution of Morita-Baylis-Hillman (MBH) acetates was developed using triethylamine (TEA) as a racemization catalyst and wild-type or engineered lipase B from Candida antarctica (CALB) as stereoselectivity-determining catalyst, leading to chiral MBH alcohols with tailor-made R or S configurations on an optional basis. In the TEA-WT CALB catalysis system, WT CALB displays excellent S enantioselectivity for a series of MBH acetates tested (up to 96% ee and 98% conversion). Reversal of enantioselectivity in favor of (R)-MBH alcohols (95% ee; 95% conversion) was achieved by generating a focused site-specific mutagenesis library composed of less than 20 variants. Molecular modeling explains the origin of stereoselectivity. |
| ESTHER : Xia_2017_ACS.Catal_7_4542 |
| PubMedSearch : Xia_2017_ACS.Catal_7_4542 |
| PubMedID: |
| Gene_locus related to this paper: canar-LipB |
| Gene_locus related to this paper: canar-LipB |
Xia B, Xu J, Xiang Z, Cen Y, Hu Y, Lin X, Wu Q (2017)
Stereoselectivity-Tailored, Metal-Free Hydrolytic Dynamic Kinetic Resolution of Morita-Baylis-Hillman Acetates Using an Engineered Lipase-Organic Base Cocatalyst
ACS Catal
7 :4542
Xia B, Xu J, Xiang Z, Cen Y, Hu Y, Lin X, Wu Q (2017)
ACS Catal
7 :4542