Lipase-catalyzed esterification in water enabled by nanomicelles. Applications to 1-pot multi-step sequences
Vani Singhania1, Margery Cortes-Clerget1, Jade Dussart-Gautheret1
1Department of Chemistry and Biochemistry, University of California Santa Barbara CA 93106 USA lipshutz@chem.ucsb.edu.
Abstract:
Esterification in an aqueous micellar medium is catalyzed by a commercially available lipase in the absence of any co-factors. The presence of only 2 wt% designer surfactant, TPGS-750-M, assists in a 100% selective enzymatic process in which only primary alcohols participate (in a 1 : 1 ratio with carboxylic acid). An unexpected finding is also disclosed where the simple additive, PhCF3 (1 equiv. vs. substrate), appears to significantly extend the scope of usable acid/alcohol combinations. Taken together, several chemo- and bio-catalyzed 1-pot, multi-step reactions can now be performed in water.
Related Concept Videos
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
Esters to Carboxylic Acids: Saponification
The reaction requires a base in stoichiometric amounts, which participates in the reaction and is not regenerated later. So, the base acts as a...
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism
Alkylation of β-Diester Enolates: Malonic Ester Synthesis


