MIPs logo MIPdatabase      MIP2018 Conference website
Custom Search
Reference type: Journal
Authors: Chaput L, Marton Z, Pineau P, Domon L, Tran V, Graber M
Article Title: Enhancing the enantioselectivity of CALB by substrate imprinting: A combined experimental and molecular dynamics simulation model study.
Publication date: 2012
Journal: Journal of Molecular Catalysis B: Enzymatic
Volume: 84
Page numbers: 55-61.
DOI: 10.1016/j.molcatb.2012.04.017
Alternative URL: http://www.sciencedirect.com/science/article/pii/S1381117712001075

Abstract: Kinetic resolution of pentan-2-ol by CALB catalyzed enantioselective transesterification, with various alkylpropanoate acyl donors, was studied in a solid-gas reactor. Results show that the leaving alkoxy group influences the enantiomeric ratio of the reaction. Resolution of pentan-2-ol with methyl propanoate gives an enantiomeric ratio of 62. Esters with longer linear alkyl chains, from ethyl to pentyl propanoate give higher enantiomeric ratios, comprised between 103 and 117. Enantiopure ester (R)-1-methylpentyl propanoate increases the enantiomeric ratio to 140 compared with E = 120 for the racemic mixture. In contrast, enantiopure (S)-1-methylpentyl propanoate decreases the enantiomeric ratio to 72. Our data support the notion of an imprinting effect or ''ligand-induced enzyme memory'' caused by the shape of the leaving alcohol. To simulate the imprinting effect caused by the alkoxy part of the acyl donor, molecular modeling studies were performed with both (R)- and (S)-enantiopure 1-methylpentyl propanoate. To investigate how the first step of the reaction, through the first tetrahedral intermediate, affects the enzyme conformation depending on the enantiopure ester substrate used, 20 ns molecular dynamics simulations were carried out. Clustering analysis was done to study relevant conformations of the systems. Differences in the global conformation of the enzyme between systems with R or S enantiomers were not observed. Interestingly however, orientation of the partially buried side chain for Ile285 was affected. This could explain the increased enantiomeric ratio observed with the substrate ester (R)-1-methylpentyl propanoate due to an improved (R)-pentan-2-ol/enzyme interaction
Template and target information: bioimprinting
Author keywords: enantioselectivity, Imprinting effect, kinetics, Candida antarctica lipase B, molecular modeling

  mipdatabase.com logo imprinters do it in bulk shirt  Science Teacher peptide mug  Perpetual student shirt

Molecules Special Issue call     Sensors Special Issue call

Join the Society for Molecular Imprinting
Logo of the Society for Molecular Imprinting

New items RSS feed
new items RSS feed  View latest updates

Sign-up for e-mail updates:
Choose between receiving an occasional newsletter or more frequent e-mail alerts.
Click here to go to the sign-up page.

Is your name elemental or peptidic? Enter your name and find out by clicking either of the buttons below!
Other products you may like:
view listings for MIP books on eBay:
US listings   UK listings

Searching for Molecular Imprinting books on Amazon.com:
Molecular Imprinting
Imprinted Polymers
Polymer Chemistry
Organic Chemistry

Find what you need at Amazon.com

Lab supplies from Amazon