Modern Biocatalysis: Stereoselective and Environmentally Friendly Reactions

This reference covers the wide and rapidly growing field of biocatalysis. It combines complementary expertise from such areas as microbiology, enzymology, molecular biology structural biology and organic chemistry, thus highlighting the interdisciplinary nature of the subject. With its special focus on progress and new developments towards environmentally beneficial reactions with high levels of selectivity for the production of key compound classes, this book will enlighten both chemists and biologists as to the advances and opportunities existing in enzyme catalysis.

Table of Contents:
FLUORESCENCE ASSAYS FOR BIOTRANSFORMATIONS Introduction Alcohol Dehydrogenases (ADHs) and Aldolases Lipases and Esterases Other Hydrolases Baeyer-Villigerases IMMOBILIZATION AS A TOOL FOR IMPROVING ENZYMES Introduction Adsorption/Electrostatic Interactions Encapsulation Covalent Binding/Cross-Linking CONTINUOUS-FLOW MICROCHANNEL REACTORS WITH SURFACE-IMMOBILIZED BIOCATALYSTS Introduction Biocatalytic Synthesis Using Microreaction Technology with Free and Immobilized Enzymes Novel Microfluidic Immobilized Enzyme Reactors Enzymatic Hydrolysis of Lactose Biocatalytic Process Intensification Using Microreaction Technology ACTIVITY AND STABILITY OF PROTEASES IN HYDROPHILIC SOLVENTS Introduction Activity and Selectivity of Proteases in Synthesis of Carbohydrate Fatty Acid Esters Enzyme Stability and Conformation Solvent Engineering IMPORTANCE OF ENZYME FORMULATION FOR THE ACTIVITY AND ENANTIOSELECTIVITY OF LIPASES IN ORGANIC SOLVENTS Introduction Lipase Formulations and their Activity and Enantioselectivity in Neat Organic Solvent Why do Additives Affect the Activity and Enantioselectivity of Lipases in Organic Solvent? DIRECT ESTERIFICATION WITH DRY MYCELIA OF MOLDS: A (STEREO)SELECTIVE, MILD AND EFFICIENT METHOD FOR OBTAINING STRUCTURALLY DIVERSE ESTERS Mycelia and Biotransformations in Organic Media Screening and Microbiological Aspects Production of Acetate Stereoselective Esterifications of Racemic Alcohols Stereoselective Esterifications of Racemic Carboxylic Acids Partition Phenomena and Equilibrium of Esterification Reactions FACTORS AFFECTING ENANTIOSELECTIVITY: ALLOSTERIC EFFECTS How to Provide Enantiopure Compounds Factors Affecting the Enantiomeric Ratio E Asymmetrization of Prochiral Compounds KINETIC RESOLUTION OF SEC-ALCOHOL IN NON-CONVENTIONAL MEDIA Introduction SCFs - Replacement for Organic Solvents in Biocatalysis Effect of Pressure Effect of the Acyl Donor/Alcohol Molar Ratio ILs - Solvents for Sustainable Technology in Biocatalysis ILs, Based on the N,N'-Dialkylimidazolium Cations as Reaction Media ILs/SCFs Biphasic Systems as Promising Media for Biocatalysis The [bmim][PF6]/SC-CO2 System as a Reaction Media Effect of Acyl Donor Concentration STRATEGIES FOR THE BIOCATALYTIC LIPOPHILIZATION OF PHENOLIC ANTIOXIDANTS Introduction Materials and Methods Results and Discussion BIOCATALYSIS APPLIED TO THE SYNTHESIS OF NUCLEOSIDE ANALOGS Introduction Chemoenzymatic Modification of the Sugar Resolution and Anomeric Separation Biotransformations that Modify the Base Transglycosylation for the Synthesis of Nucleosides EFFICIENT FRUCTOOLIGOSACCHARIDE SYNTHESIS WITH A FRUCTOSYLTRANSFERASE FROM ASPERGILLUS ACULEATUS Introduction Purification of Fructosyltransferase in Pectinex Ultra SP-L Properties of Fructosyltransferase from A. aculeatus Immobilization of Fructosyltransferase from A. aculeatus Fructooligosaccharide Production Using Sugar Beet Syrup and Molasses HYDANTOIN RACEMASE: THE KEY ENZYME FOR THE PRODUCTION OF OPTICALLY PURE ALPHA-AMINO ACIDS Introduction Search for New Hydantoin Racemases and Molecular Characterization Biochemical Characterization of Hydantoin Racemase Enzymes Substrate Enantioselectivity and Kinetic Analysis of Hydantoin Racemases Proposal for a Reaction Mechanism of Hydantoin Racemase Enzymes Design of a Tailormade Recombinant Biocatalyst Including Hydantoin Racemase Enzymes for Optically Pure D-Amino Acid Production CHEMO-ENZYMATIC DERACEMIZATION METHODS Introduction Deracemization Methods for Alpha- and Beta-Hydroxy Acids Deracemization of Alpha-Hydroxy Nitriles Deracemization of Alpha-Amino Acids Useful Enzymes for Deracemization Methods NITRILASES FROM FILAMENTOUS FUNGI Introduction Distribution and Evolutionary Relationship of Fungal Nitrilases Structural Properties Catalytic Properties NITRILASE- AND NITRILE HYDRATASE-CATALYZED ENANTIOSELECTIVE PREPARATION OF NON-PROTEINOGENIC AMINO ACIDS Introduction Nitrilase Hydratase/Amidase Biotransformations Nitrilase Biotransformations NITRILASES IN THE ENANTIOSELECTIVE SYNTHESIS OF ALPHA-HYDROCYCARBOXYLIC ACIDS Routes to Enantiomerically Pure Alpha-Hydroxycarboxylic Acids Nitrilase-Mediated Hydrolysis of Cyanohydrins A Bienzymatic Approach to Enantiopure 2-Hydrocycarboxylic Acids Stabilization of NLases as Cross-Linked Enzyme Aggregates Hydrocyanation and Hydrolysis in a Bienzymatic Cascade Nitrilases Acting as Nitrile Hydratases UF-MEMBRANE BIOREACTORS FOR KINETICS CHARACTERIZATION OF NITRILE HYDRATASE-AMIDASE-CATALYZED REACTIONS: A SHORT SURVEY Introduction Experiment Design Temperature Dependence of the Nitrile Hydratase-Amidase Cascade System CSMR Investigations Substrate Concentration Effects on the Reaction Rate, Enzyme Stability, Substrate Conversion, and Reactor Capacity ENZYMES CATALYZING C-C BOND FORMATION FOR THE SYNTHESIS OF MONOSACCHARIDE ANALOGS Introduction Recent Syntheses Involving Transketolase and Fructose-1,6-bisphosphate Aldolase Modification of Substrate Specificity of Yeast Transketolase NOVEL STRATEGIES IN ALDOLASE-CATALYZED SYNTHESIS OF IMINOSUGARS Introduction DHAP-Aldolase-Mediated Synthesis of Iminosugars from N-Cbz-Amino Aldehydes D-Fructose-6-Phosphate Aldolase as Catalyst for Iminosugar Synthesis BIOCATALYTIC ASYMMETRIC OXIDATIONS WITH OXYGEN Introduction Biocatalytic Asymmetric Oxidations with Oxidases Biocatalytic Asymmetric Oxidations with Peroxidases Biocatalytic Asymmetric Oxidations with Dehydrogenases Biocatalytic Asymmetric Oxidations with Monooxygenases Biocatalytic Asymmetric Oxidations with Dioxygenases Biocatalytic Asymmetric Oxidations with Other Enzyms SECOND GENERATION BAEYER-VILLIGER BIOCATALYSTS Introduction VBMO Enzyme Platform Engineering of BVMOs Baeyer-Villiger Biooxidation in Synthetic Chemistry BVMOs in Stereoselective Sulfoxidations Towards a Technology Platform

About the Author :
Wolf-Dieter Fessner obtained his PhD from the University of Freiburg, following which he carried out postdoctoral research at Harvard University with George Whitesides and at the University of Southern California with George Olah. Since 1998 he has been Full Professor of Organic Chemistry at the Technische Universitat Darmstadt. His primary research interest is focused on the development of practical methods for enzymatic carbon-carbon bond formation and oligosaccharide synthesis, and on the interface between chemical and biological catalysis. Thorleif Anthonsen is Professor of Organic Chemistry at The Norwegian University of Science and Technology, NTNU, in Trondheim. He has been a post doc/visiting scholar at Glasgow University, UK, at UCLA Los Angeles, with Donald Cram at MIT Cambridge, USA, with Alexander Klibanov and at Cytel Corporation, San Diego. He has led the biocatalysis group at NTNU whose research focused on synthesis of enantiopure compounds directed towards production of chiral drugs. In 2001 he initiated COST action D25, Applied Biocatalysis, which he also chaired from beginning to end. Professor Anthonsen's primary research interests are natural product chemistry and biocatalysis in organic chemistry.

Review :
?With its special focus on progress and new developments towards environmentally beneficial reactions with high levels of selectivity for the production of key compound classes, this book will enlighten both chemists and biologists as to the advances and opportunities existing in enzyme catalysis.? (Organic Chemistry Portal/ Organische-Chemie, 2009) ?Books of this type are highly valuable in that each chapter is written by an acknowledged expert in the field and hence the reader is directed to the key developments and seminal contributions in the particular field.? (ChemBioChem , June 2009)