Synthetic Methods for Biologically Active Molecules. Exploring the Potential of Bioreductions

  • ID: 2505289
  • Book
  • 408 Pages
  • John Wiley and Sons Ltd
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This useful reference focuses on the currently available toolbox of bio–catalysed reductions of C=O, C=C and formal C=N bonds to show which transformations can be reliably used in manufacturing processes and which still require improvements.

Following an introductory chapter, chapters 2–4 present the synthetic strategies that are currently available for the reduction of C=C and C=O bonds and for reductive amination, by means of whole–cell catalysts and isolated enzymes. Chapters 5–7 go on to describe the improvements achieved thus far, illustrating the current versatility of enzymes in organic synthesis. Chapters 8–12 present the improvements brought about by the optimization of reaction conditions, and the use of particular synthetic sequences. The final chapter describes practical applications of bio–reductions for the synthesis of active pharmaceutical ingredients.

With its excellent and comprehensive overview, this book will be of great interest to those working in academia and industry.

From the contents:

∗ Development of Sustainable Biocatalyzed Reduction Processes for Organic Chemists

∗ Reductases: From Natural Diversity to Biocatalysis and Emerging Enzymatic Activities.

∗ Synthetic Strategies Based on C=C Bioreductions

∗ Synthetic Strategies Based on C=O Bioreductions

∗ Development of Novel Enzymes for the Improved Reduction of C=C Double Bonds

∗ Development of Novel Enzymes for the Improved Reduction of C=O Double Bonds

∗ Synthetic Applications of Aminotransferases

∗ Strategies for Cofactor Regeneration in Biocatalyzed Reductions

∗ Effects of Solvent System and Substrate Loading in Bioreduction

∗ Perspectives in the Use of In–Situ Product Removal (ISPR) Techniques in Bioreductions

∗ Multi–Enzymatic Cascade Reactions Based on Reduction Processes

∗ Relevant Practical Applications of Bioreduction Processes in the Synthesis of Active Pharmaceutical Ingredients

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Preface

DEVELOPMENT OF SUSTAINABLE BIOCATALYTIC REDUCTION PROCESSES FOR ORGANIC CHEMISTS

Introduction

Biocatalytic Reductions of C=O Double Bonds

Biocatalytic Reductions of C=C Double Bonds

Biocatalytic Reductions of Imines to Amines

Biocatalytic Reductions of Nitriles to Amines

Biocatalytic Deoxygenation Reactions

Emerging Reductive Biocatalytic Reactions

Reaction Engineering for Biocatalytic Reduction Processes

Summary and Outlook

REDUCTASES: FROM NATURAL DIVERSITY TO ESTABLISHED BIOCATALYSIS AND TO EMERGING ENZYMATIC ACTIVITIES

Reductases: Natural Occurrence and Context for Biocatalysis

Emerging Cases of Reductases in Biocatalysis

Concluding Remarks

SYNTHETIC STRATEGIES BASED ON C=C BIOREDUCTIONS FOR THE PREPARATION OF BIOLOGICALLY ACTIVE MOLECULES

Introduction

Bioreduction of Alpha,Beta–Unsaturated Carbonyl Compounds

Bioreduction of Nitroolefins

Bioreduction of Alpha,Beta–Unsaturated Carboxylic Acids and Derivatives

Bioreduction of Alpha,Beta–Unsaturated Nitriles

Concluding Remarks

SYNTHETIC STRATEGIES BASED ON C=O BIOREDUCTIONS FOR THE PREPARATION OF BIOLOGICALLY ACTIVE MOLECULES

Introduction

Synthesis of Biologically Active Compounds through C=O Bioreduction

Other Strategies to Construct Biologically Active Compounds

Summary and Outlook

PROTEIN ENGINEERING: DEVELOPMENT OF NOVEL ENZYMES FOR THE IMPROVED REDUCTION OF C=C DOUBLE BONDS

Introduction

The Protein Engineering Process and Employed Mutagenesis Methods

Examples of Rational Design of Old Yellow Enzymes

Evolving Old Yellow Enzymes (OYEs)

Conclusions and Perspectives

PROTEIN ENGINEERING: DEVELOPMENT OF NOVEL ENZYMES FOR THE IMPROVED REDUCTION OF C=O DOUBLE BONDS

Introduction

Detailed Characterization of PAR

Detailed Characterization of LSADH

Engineering of PAR for Increasing Activity in 2–Propanol/Water Medium

Application of Whole–Cell Biocatalysts Possessing Mutant PARs and LSADH

Engineering of Beta–Keto Ester Reductase (KER) for Raising Thermal Stability and Stereoselectivity

New Approach for Engineering or Obtaining Useful ADHs/Reductases

SYNTHETIC APPLICATIONS OF AMINOTRANSFERASES FOR THE PREPARATION OF BIOLOGICALLY ACTIVE MOLECULES

Introduction

Applications

Challenges

Future Research Needs

Conclusions

STRATEGIES FOR COFACTOR REGENERATION IN BIOCATALYZED REDUCTIONS

Introduction: NAD(P)H as the Universal Reductant in Reduction Biocatalysis

The Most Relevant Cofactor Regeneration Approaches – and How to Choose the Most Suitable One

Coupling the Reduction Reaction to a Regeneration Reaction Producing a Valuable Compound

Avoiding NAD(P)H: Does it Also Mean Avoiding the Challenge?

Conclusions

SOLVENT EFFECTS IN BIOREDUCTIONS

Introduction

Solvent Systems for Biocatalytic Reductions

Solvent Control of Enzyme Selectivity

Concluding Remarks

APPLICATION OF IN SITU PRODUCT REMOVAL (ISPR) TECHNOLOGIES FOR IMPLEMENTATION AND SCALE–UP OF BIOCATALYTIC REDUCTIONS

Introduction

Process Requirements for Scale–Up

Bioreduction Process Engineering

In situ Product Removal

Biocatalyst Format

Selected Examples

Future Outlook

Conclusions

BIOREDUCTIONS IN MULTIENZYMATIC ONE–POT AND CASCADE PROCESSES

Introduction

Coupled Oxidation and Reduction Reactions

Consecutive and Cascade One–Pot Reductions

Cascade Processes, Including Biocatalyzed Reductive Amination Steps

Other Examples of Multienzymatic Cascade Processes, Including Bioreductive Reactions

DYNAMIC KINETIC RESOLUTIONS BASED ON REDUCTION PROCESSES

Introduction

Cyclic Compounds

Acyclic Alpha–Substituted–Beta–Keto Esters and 2–Substituted–1,3–Diketones

Acyclic Ketones and Aldehydes

Conclusions

RELEVANT PRACTICAL APPLICATIONS OF BIOREDUCTION PROCESSES IN THE SYNTHESIS OF ACTIVE PHARMACEUTICAL INGREDIENT

Introduction

Ketoreductases

Ene Reductases

Others

Bioreduction–Supported Processes

Outlook

Index

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Elisabetta Brenna received her laurea (1989) and PhD (1993) in chemistry from the University of Milan. In 1996, she became Assistant Professor at Politecnico di Milano, where she is now Associate Professor. Her main scientific interests are the enzyme–mediated synthesis of the single enantiomers of chiral biologically active compounds, and the use of the SNIF NMR technique for tracing back the synthetic history of active pharmaceutical ingredients and synthetic flavourings. She is author of more than 120 publications in international journals.
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