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

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...

Impact of aqueous micellar media on biocatalytic transformations involving transaminase (ATA); applications to chemoenzymatic catalysis

“…Previously, TPGS-750-M was the surfactant of choice in all cases (i.e., KREDs, EREDs, and lipases). 13,15,16 Interestingly, ATAs appear to be surfactant-dependent, suggesting that several be screened in anticipation of finding a "match" that maximizes levels of educt-to-product conversion. This discovery was made upon analyses of six educts (Table 1), each treated with an ATA found (in preliminary screenings) to give the best extent of conversion in the absence of amphiphile (i.e., buffer only).…”

“…Previously, TPGS-750-M, in general, was the most effective surfactant in cases involving KREDs, EREDs, and lipases. 15,17,18 Unexpectedly, the observed efficiency of an ATA appears to be surfactant-dependent, suggesting that several amphiphiles need to be screened in anticipation of finding a "match" that maximizes levels of substrate-toproduct conversion. In this report the trend associated with various surfactants on the extent of conversion for several representative ketones is assessed, using commercially available ATAs.…”

An environmentally responsible synthesis of the antitumor agent lapatinib (Tykerb)

“…, by the pharmaceutical industry; 23 (b) utilize far less precious metal-containing catalysts, and yet, realize the same outcomes with oftentimes greater selectivities, higher yields, and in less time; 24 (c) carry out reactions under milder conditions that in most cases will lead to far better impurity profiles, thereby streamlining and simplifying product purification. And while the example of lapatinib synthesis in no way is suggestive that existing routes to pharmaceuticals currently on the market should be redone notwithstanding the obvious benefits in terms of both environmental and economic factors, it does highlight the favorable options available today to medicinal and process chemists, especially now that the merging of chemo- and bio-catalysis into 1-pot sequences has been amply demonstrated, 25 all in Nature's “solvent”: water.…”

Cascade Processes with Micellar Reaction Media: Recent Advances and Future Directions

“…The biocatalyzed reaction could be followed, without isolation, by chemocatalysis (e.g., Pd-catalyzed Suzuki-Miyaura coupling). As many as five steps could be performed sequentially in water, with overall yields of 65% [ 154 ].…”