Lipase-catalyzed esterification in water enabled by nanomicelles. Applications to 1-pot multi-step sequences

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.

Automated summary

In an aqueous micellar medium, commercially available lipase catalyzes esterification with high selectivity in the absence of any co-factors, aided by only 2% designer surfactant TPGS-750-M. An unexpected finding shows that the simple additive PhCF3 can significantly expand the range of usable acid/alcohol combinations. This allows for multiple chemo- and bio-catalyzed 1-pot, multi-step reactions to be performed in water.