Hydrolases in Organic Synthesis – Regio– and Stereoselective Biotransformations

Uwe Bornscheuer was born in 1964 and studied chemistry at the University of Hannover, Germany, where he graduated with his Diploma in 1990. After receiving his PhD in Chemistry in 1993 at the Institute of Technical Chemistry at the same university, he spent a postdoctoral year at the University of Nagoya, Japan. He then returned to Germany and joined the Institute of Technical Biochemistry at the University of Stuttgart, where he finished his Habilitation in 1998. Since 1999 he has been Professor for Technical Chemistry and Biotechnology at the University of Greifswald. His main research interest is the application of biocatalysts in the synthesis of optically active compounds and in lipid modification. Romas Kazlauskas studied chemistry at the Massachusetts Institute of Technology (PhD) and Harvard University (postdoc with G. M. Whitesides). He worked at General Electric Company (1985-1988) and McGill University, Montreal, Canada (1988-2003) and is currently an associate professor of Biochemistry, Molecular Biology, and Biophysics at the University of Minnesota, Twin Cities. He is an expert in enzyme selectivity, especially enantioselectivity. His current work focuses on the design of new enzymatic reactions and the molecular basis of enzyme enantioselectivity.

1 Introduction.2 Designing Enantioselective Reactions.2.1 Kinetic Resolutions.2.2 Asymmetric Syntheses.3 Choosing Reaction Media: Water and Organic Solvents.3.1 Hydrolysis in Water.3.2 Transesterifications and Condensations in Organic Solvents.3.3 Other Reaction Media.3.4 Immobilization.4 Protein Sources and Optimization of Biocatalyst Performance.4.1 Accessing Biodiversity.4.2 Creating Improved Biocatalysts.4.3 Catalytic Promiscuity in Hydrolases.5 Lipases and Esterases.5.1 Availability, Structures and Properties.5.2 Survey of Enantioselective Lipase-Catalyzed Reactions.5.3 Chemo-and Regioselective Lipase-Catalyzed Reactions.5.4 Reactions Catalyzed by Esterases.6 Proteases and Amidases.6.1 Occurrence and Availability of Proteases and Amidases.6.2 General Features of Subtilisin, Chymotrypsin, and Other Proteases and Amidases.6.3 Structures of Proteases and Amidases.6.4 Survey of Enantioselective Protease-and Amidase-Catalyzed Reactions.7 Phospholipases.7.1 Phospholipase A1.7.2 Phospholipase A2.7.3 Phospholipase C.7.4 Phospholipase D.8 Epoxide Hydrolases.8.1 Introduction.8.2 Mammalian Epoxide Hydrolases.8.3 Microbial Epoxide Hydrolases.9 Hydrolysis of Nitriles.9.1 Introduction.9.2 Mild Conditions.9.3 Regioselective Reactions of Dinitriles.9.4 Enantioselective Reactions.10 Other Hydrolases.10.1 Glycosidases.10.2 Haloalcohol Dehalogenases.10.3 Phosphotriesterases.Abbreviations.References.Index.