Lipase-catalyzed esterification in water enabled by nanomicelles. Applications to 1-pot multi-step sequences |
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| Authors: | Vani Singhania Margery Cortes-Clerget Jade Dussart-Gautheret Bhornrawin Akkachairin Julie Yu Nnamdi Akporji Fabrice Gallou Bruce H. Lipshutz |
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| Affiliation: | Department of Chemistry and Biochemistry, University of California, Santa Barbara CA 93106 USA.; Program on Chemical Biology, Chulabhorn Graduate Institute, Center of Excellence on Environmental Health and Toxicology (EHT), Ministry of Education, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210 Thailand ; Novartis Pharma AG, CH-4057 Basel Switzerland |
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| 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.Esterification in an aqueous micellar medium is catalyzed by a commercially available lipase in the absence of any co-factors. |
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