Biocatalysis in organic synthesis

The Editors are most grateful to the authors who have submitted details of their procedures in the prescribed format for inclusion in this book. We hope that this book will increase the exposure of these methods to the chemical community and contribute to the expanded employment of biocatalysis in organic synthesis. 

Tramper J, VanderPlas HC, Linko P (eds) (1985) Biocatalysis in organic synthesis. Elsevier, Amsterdam... 

Knowles [1] and Homer [2] independently discovered homogeneous asymmetric catalysts based on rhodium complexes bearing a chiral monodentate tertiary phosphine. Continued efforts in this field have produced hundreds of asymmetric catalysts with a plethora of chiral ligands [7], dominated by chelating bisphosphines, that are highly active and enantioselective. These catalysts are beginning to rival biocatalysis in organic synthesis. The evolution of these catalysts has been chronicled in several reviews [8 13]. 

Nearly eight years have passed since we the First Edition of Enzyme Catalysis in Organic Synthesis" was issued but much of what we had written in its preface then still applies today. The application of biocatalysis in organic synthesis is a powerful technique. It has grown steadily and today this field is well-established in both academia and industry. With increasing application and acceptance the need for a comprehensive and up to date overview of the state of the art has grown. In addition numerous colleagues have approached us and asked for an update of the Handbook . 

Park JB (2007) Oxygenase-based whole-cell biocatalysis in organic synthesis. J Microbiol Biotechnol 17 379-392... 

Comprehensive review about biocatalysis in organic synthesis Drauz, K., Groger, H., and May, O. (eds) (2012) Enzyme Catalysis in Organic Synthesis, 3rd edn,... 

This is the most common application of biocatalysis in organic synthesis and represents the majority of published examples. Enzymes that catalyze acyl transfer reactions of esters and amides are widely distributed in nature and belong to the lipase/esterase and protease/amidase families, respectively. They play key roles in the metabolism of lipids and proteins and the choice of names, lipase versus esterase, is subject to debate. Normally, acyl ttansfer occurs almost exclusively to water, resulting in hydrolysis. This is particularly valuable for amide hydrolysis that normally requires forcing conditions and strong acid or... 

Biocatalysis in organic synthesis has a longstanding history and wide applicability in the enantioselective reduction of ketones (150, 151], Many enzymatic protocols provide reliable, scalable, and inexpensive routes to optically active alcohols consequently, such transformations have been extensively employed in industrial applications. A few representative examples of enzymatic reductions of ketones on large scale, giving hydroxy acids 243 [147, 152) and 245 (153) with exceptional enantioselectivities and yields, are shown below (Equations 18 and 19). 

MD Lilly, JM Woodley. In J Tramper, HC Van der Plas, P Linco, eds. Biocatalysis in Organic Synthesis. Amsterdam Elsevier, 1985, pp 179-192. 

There are many enzymes that are commercially available, though the biotransformation literature and our own experience shows that in fact most biocatalysis is done with a relatively small subset of very frequently used enzymes. For a comprehensive review of biocatalysis in organic synthesis, the reader should refer to Drauz and Waldmann s two-volume Enzyme Catalysis in Organic Synthesis [1]. Many commercially available enzymes were not developed with organic synthesis in mind but are used in other industries. Examples include proteases like subtilisin, used in detergent formulations, or lipases, again used in detergents or in cheese and flavor production. There is a wide variety of ways in... 

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