Throughout evolution, enzymatic catalysis has advanced, overseen by Nature, using water as the reaction medium. But what was in the water over the millennia during which the “chemistry of life” was happening? Surely the water in the streams, rivers, lakes, and oceans was anything but pristine. Rather, it was almost certainly “dirty”, where this “dirt” included the likes of simple vesicles, membranes, salts, and, notwithstanding critical micelle concentrations required along the way, even micellar arrays. And just as today we rely on these bio-like species to enable crucial biochemical processes in vivo (such as in the membranes of mitochondria, where CoQ10 mediates electron-transport leading to human energy production), so might the same biochemical species have assisted with enzymatic evolution. In this presentation, the roles played in modern organic synthesis by designer surfactants, as the “dirt” in the water, will be discussed. Included in this discussion will be both amphiphiles TPGS-750-M and its (soon to be disclosed) biodegradable, ‘drop in’ replacement Savie. Their impact on reactions catalyzed by various enzymes (e.g., KREDs, EREDs, ATAs, lipases, and IREDs) will be shown, as will opportunities for multi-step processes that combine both chemocatalysis and biocatalysis, all in 1-pot, and all in water. The examples below are illustrative of the (unlimited) possibilities applying chemoenzymatic catalysis to organic synthesis.1-4

Chemoenzymatic catalysis: Clean chemistry in “dirty” water

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ACS Spring 2023

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