Cascade Biocatalysis (eBook)

Dr. Sergio Riva is the Director of the Institute of the Chemistry of Molecular Recognition (ICRM) of the Italian National Council of Research (C.N.R.), where he has been working since 1984, and "Professore a Contratto"at the University of Modena and Reggio Emilia since 2000. He took his Laurea in Chemistry at Milano University in 1983 and his Diploma di Specialità in Organic Synthesis at Milano Politecnico in 1989. He spent one year (1987) at M.I.T. (Cambridge, USA) working with Prof. A. Klibanov. In 1993 he was awarded the Ciamician medal by the Organic Chemical Division of the Italian Chemical Society for his research activity in biocatalysis. His research activity is documented by more than 160 publications reporting on the isolation and characterization of different groups of enzymes (hydrolases, dehydrogenases, oxynitrilases, aldolases, laccases, glycosyltransferases), and on the use of these biocatalysts for the selective modification of natural compounds (steroids, alkaloids, terpenes, sugars and natural glycosides) and chiral synthons. 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 Universität Darmstadt. His primary research interest is focused on the development of practical methods for asymmetric synthesis at the interface between chemical and biological catalysis. A distinctive element in his research is the assembly and development of one-pot, multi-enzymatic reaction cascades for biocatalytic carbon-carbon bond formation and oligosaccharide synthesis, including the characterization and engineering of novel enzyme catalysts for a broader spectrum of substrate specificity

Preface

DIRECTED EVOLUTION OF LIGNINOLYTIC OXIDOREDUCTASES: FROM FUNCTIONAL EXPRESSION TO STABILIZATION AND BEYOND
Introduction
Directed Molecular Evolution
The Ligninolytic Enzymatic Consortium
Directed Evolution of Laccases
Directed Evolution of Peroxidases and Peroxygenases
Saccharomyces cerevisiae Biomolecular Tool Box
Conclusions and Outlook

NEW TRENDS IN THE IN SITU ENZYMATIC RECYCLING OF NAD(P)(H) COFACTORS
Introduction
Recent Advancements in the Enzymatic Methods for the Recycling of NAD(P)(H) Coenzymes and Novel Regeneration Systems
Conclusions

MONOOXYGENASE-CATALYZED REDOX CASCADE BIOTRANSFORMATIONS
Introduction
Enzymatic Oxygenation
Effective Cofactor Recycling
In Vitro Multistep Biocatalysis
Combined In Vitro and In Vivo Multistep Biocatalysis
In Vivo Multistep Biocatalysis
Chemo-Enzymatic Cascade Reactions
Conclusions and Outlook

BIOCATALYTIC REDOX CASCADES INVOLVING W-TRANSAMINASES
Introduction
General Features of w-Transaminases
Linear Cascade Reactions Involving w-Transaminases
Concluding Remarks

MULTI-ENZYME SYSTEMS AND CASCADE REACTIONS INVOLVING CYTOCHROME P450 MONOOXYGENASES
Introduction
Physiological Cascade Reactions Involving P450s
Artificial Cascade Reactions Involving P450s
Conclusions and Outlook

CHEMO-ENZYMATIC CASCADE REACTIOS FOR THE SYNTHESIS OF GLYCOCONJUGATES
Introduction
Sequential Syntheses
One-Pot Syntheses
Convergent Syntheses
Conclusion

SYNERGIES OF CHEMISTRY AND BIOCHEMISTRY FOR THE PRODUCTION OF BETA-AMINO ACIDS
Introduction
Dihydropyrimidinase
N-Carbomoyl-Beta-Alanine Amidohydrolase
Bienzymatic System for Beta-Amino Acid Production
Conclusions and Outlook

RACEMIZABLE ACYL DONORS FOR ENZYMATIC DYNAMIC KINETIC RESOLUTION
Introduction
The Tools
Applications of DKR to Acyl Compounds
Conclusions

STEREOSELECTIVE HYDROLASE-CATALYZED PROCESSES IN CONTINUOUS-FLOW MODE
Introduction
Enzyme-Catalyzed Stereoselective Reactions in Continuous-Flow Systems
Outlook and Perspectives

PERSPECTIVES ON MULTIENZYME PROCESS TECHNOLOGY
Introduction
Multienzyme System Classification
Biocatalyst Options
Reactor Options
Process Development
Process Modeling
Future
Concluding Remarks

NITRILE CONVERTING ENZYMES INVOLVED IN NATURAL AND SYNTHETIC CASCADE REACTIONS
Introduction
Natural Cascades
Artificial Cascades
Conclusions and Future Use of These Enzymes

MINING GENOMES FOR NITRILASES
Strategies in Nitrilase Search
Diversity of Nitrilase Sequences
Structure-Function Relationships
Enyzme Properties and Applications
Conclusions

KEY-STUDY ON THE KINETIC ASPECTS OF THE IN SITU NHASE/AMASE CASCADE SYSTEM OF M. imperiale RESTING CELLS FOR NITRILE BIOCONVERSION
Introduction
The Temperature Effect on the NHase-Amidase Bi-Enzymatic Cascade System
Effect of Nitrile Concentration on NHase Activity and Stability
Effect of Nitrile on the AMase Activity and Stability
Concluding Remarks

ENZYMATIC STEREOSELECTIVE SYNTHESIS OF BETA-AMINO ACIDS
Introduction
Preparation of Beta-Amino Acids
Nitrile Hydrolysis Enzymes
Conclusion

NEW APPLICATIONS OF TRANSKETOLASE: CASCADE REACTIONS FOR ASSAY DEVELOPMENT
Introduction
Cascade Reactions for Assaying Transketolase Activity In Vitro Selection
Conclusion

ALDOLASES AS CATALYST FOR THE SYNTHESIS OF CARBOHYDRATES AND ANALOGS
Introduction
Iminocyclitol and Aminocyclitol Synthesis
Carbohydrates and Other Polyhydroxylated Compounds
Conclusions

ENZYMATIC GENERATION OF SIALCONJUGATE DIVERSITY
Introduction
A Generic Strategy for the Synthesis of Sialconjugate Libraries
Cascade Synthesis of Neo-Sialconjugates
Conclusions

METHYLTRANSFERASES IN BIOCATALYSIS
Introduction
SAM-Dependent Methyltransferases
Conclusion and Outlook

CHEMOENZYMATIC MULTISTEP ONE-POT PROCESSES
Introduction: Why Chemoenzymatic Cascades and Why One-Pot Processes?
Concepts of Chemoenzymatic Processes
Combination of Substrate Isomerization and their Derivatization with Chemo- and Biocatalysts Resulting in Dynamic Kinetic Resolutions and Related Processes
Combination of Substrate Synthesis (Without Isomerization) and Der