Ionic Liquids in Biotransformations and Organocatalysis Solvents and Beyond

Preface xv

Contributors xvii

PART I FUNDAMENTALS 1

1 IONIC LIQUIDS: DEFINITION, APPLICATIONS, AND CONTEXT FOR BIOTRANSFORMATIONS AND ORGANOCATALYSIS 3
Pablo Domínguez de María

1.1 Ionic Liquids: Definition, Development, and Overview of Current Main Applications 3

1.2 On the Greenness of ILs: Toward the Third Generation of ILs and DES 6

1.3 Context of ILs in Biotransformations and Organocatalysis 12

References 13

2 IONIC LIQUIDS AND PROTEINS: ACADEMIC AND SOME PRACTICAL INTERACTIONS 15
Zhen Yang

2.1 Introduction 17

2.2 Ionic Liquids, Water, and Proteins 18

2.3 Hofmeister Effects on Biocatalysis 26

2.4 Impact of Ionic Liquids on Enzymes and Proteins 41

2.5 Protein Extraction by Means of Ionic Liquids 52

2.6 Proper Selection of Ionic Liquids for Biocatalysis 57

2.7 Concluding Remarks 65

PART II IONIC LIQUIDS IN BIOTRANSFORMATIONS 73

3 IONIC LIQUIDS IN BIOTRANSFORMATIONS: MOTIVATION AND DEVELOPMENT 75
Christina Kohlmann and Lasse Greiner

3.1 First Uses of Ionic Liquids in Biotransformations 75

3.2 Motivation to Use IL in Biotransformations 80

3.3 Challenges for the Use of IL in Biotransformations 91

4 IONIC LIQUIDS AND OTHER NONCONVENTIONAL SOLVENTS IN BIOTRANSFORMATIONS: MEDIUM ENGINEERING AND PROCESS DEVELOPMENT 103
Pedro Lozano and Eduardo García-Verdugo

4.1 Introduction: Toward Greener Catalytic Processes 103

4.2 The Importance of the Medium Engineering in Biotransformations 106

4.3 Biocatalysis in Monophasic ILs Systems 110

4.4 (Bio)catalytic Processes in SCFs 118

4.5 Multiphase Biotransformations 124

4.6 Prospects 140

5 IONIC LIQUIDS AS (CO-)SOLVENTS FOR HYDROLYTIC ENZYMES 151
Hua Zhao

5.1 Introduction 152

5.2 State-of-the-art: Lipases, Esterases, Proteases in ILs as (co-)Solvents 155

5.3 Use of ILs for (dynamic) Kinetic Resolutions ((D)KRs) 183

5.4 Hydrolase-Catalyzed Esterifi cations of Saccharides and Cellulose Derivatives in ILs 205

5.5 ILs for Glycosidases 210

5.6 Prospects 212

6 IONIC LIQUIDS AS (CO-)SOLVENTS FOR NONHYDROLYTIC ENZYMES 229
Daniela Gamenara, Patricia Saenz Méndez, Gustavo Seoane, and Pablo Domínguez de María

6.1 Ionic Liquids and Nonhydrolytic Enzymes 231

6.2 Use of ILs in Oxidoreductase-Catalyzed Enzymatic Reactions 232

6.3 ILs in Lyase-Catalyzed Reactions 253

6.4 Prospects 256

7 IONIC LIQUIDS AND WHOLE-CELL–CATALYZED PROCESSES 261
Danielle Dennewald and Dirk Weuster-Botz

7.1 Ionic Liquids Compatible with Whole-Cell Biocatalysis: Fundamentals and Design 263

7.2 Biocompatibility, Tolerance, and Accumulation in the Cell 272

7.3 State of the Art 281

7.4 Prospects 308

8 NONSOLVENT APPLICATIONS OF IONIC LIQUIDS IN BIOTRANSFORMATIONS 315
Pablo Domínguez de María and Christina Kohlmann

8.1 Introduction 315

8.2 Ionic Liquids as Additives in Biotransformations 316

8.3 Ionic Liquids for Coating Enzymes: The ILCE Concept 318

8.4 Ionic Liquids Combined with Membranes and Biotransformations 321

8.5 Ionic Liquids Anchoring Substrates 321

8.6 Ionic Liquids and Bioelectrochemistry 324

PART III IONIC LIQUIDS IN ORGANOCATALYSIS 331

9 IONIC LIQUIDS AS (CO-)SOLVENTS AND CO-CATALYSTS FOR ORGANOCATALYTIC REACTIONS 333
Štefan Toma and Radovan Šebesta

9.1 Nontraditional Media in Organocatalysis 333

9.2 Early Organocatalytic Reactions in Ionic Liquids 334

9.3 Ionic Liquids as Solvents for Organocatalytic Reactions 335

9.4 Ionic Liquids as Co-catalysts for Organocatalytic Reactions: Toward New Reactivities and Selectivities 353

9.5 Key Factors in Choosing Ionic Liquids for Organocatalysis and Prospects 355

10 "NONSOLVENT" APPLICATIONS OF IONIC LIQUIDS IN ORGANOCATALYSIS 361
Michelangelo Gruttadauria, Francesco Giacalone, Paola Agrigento, and Renato Noto

10.1 Introduction 361

10.2 Immobilizing Ionic Liquids and Organocatalysts 363

10.3 Anchoring of Organocatalyst to Ionic Liquids 378

10.4 Ionic Liquids as Organocatalysts 409

10.5 Conclusions 414

References 414

Index 419

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