Second volume of practical advice for synthetic chemists wanting to use biocatalysts.
Taal / Language : English
Inhoudsopgave:
List of Contributors xvii
Abbreviations xxi
1 Biocatalysis in the Fine Chemical and Pharmaceutical Industries 1
1.1 Introduction 1
1.2 Biotrans Outsourcing - AstraZeneca 3
1.3 Biotrans Trends - Lonza 4
1.3.1 Downstream Processing - Lonza 8
1.4 Biocatalysis in the Pharma Environment 9
1.4.1 Value Creation by Biocatalysis - Roche 9
1.4.2 Discovery Chemistry and Manufacturing in Pharma - Pfizer 12
1.4.3 Drug Metabolites and Building Blocks - Novartis 16
1.4.4 Biotrans Using Isolated Enzymes - Merck 18
1.5 Industrial Use of Hydrolases 24
1.5.1 b-Lactam Antibiotics Synthesis - GSK 24
1.5.2 Preparative Use of Phosphatases and Transglycosylases- LibraGen 26
1.5.3 Biocatalytic Desymmetrization and Dynamic Kinetic
Resolution (DKR) Processes - AstraZeneca 28
1.6 Industrial Biooxidation and Reduction 32
1.6.1 Approaches to Chiral Secondary Alcohols - Dr Reddy`s, Chirotech 32
1.6.2 Application of Alcohol Dehydrogenases and P450 Oxidation - Almac 34
1.7 Industrial Application of Transaminases - Cambrex 36
1.8 Biocatalyst Discovery and Improvement 38
1.8.1 Directed Evolution Technologies - Codexis 38
1.8.2 Discovering Novel Enzymes from Untapped Biodiversity- LibraGen 42
1.9 From Pathway Engineering to Synthetic Biology 43
1.9.1 Pathway Engineering in Yeast - Sanofi-Aventis 43
1.9.2 Application of Synthetic Biology - Ingenza 45
1.10 Prioritization of Future Biocatalysis and Synthetic Biology Needs 48
1.11 Concluding Remarks 53
Acknowledgements 54
References 54
Appendix 61
2 Reductive Amination 65
2.1 o-Transaminases - Useful Biocatalysts for Chiral Amine Synthesis 65
2.1.1 Chiral Amine Synthesis 65
Acknowledgements 67
References 68
2.2 Preparative Scale Production of a Bulky-Bulky Chiral Amine Using an Engineered Transaminase 68
2.2.1 Kilogram Scale Procedure 70
2.2.2 Conclusions 72
References 72
2.3 Synthesis of Optically Pure Amines Employing o-Transaminases 73
2.3.1 Procedure 1: Kinetic Resolution 74
2.3.2 Procedure 2: Asymmetric Reductive Amination Employing System 1 75
2.3.3 Procedure 3: Asymmetric Reductive Amination Employing System 2 76
2.3.4 Conclusion 77
References 78
2.4 A Fast, Sensitive Assay and Scale-Up of o-Transaminase Catalysed Reactions 78
2.4.1 Procedure 1: A Fast and Sensitive Assay for Measuring the Activity and Enantioselectivity of Transaminases 78
2.4.2 Procedure 2: Scale Up of a TA-Catalysed Preparation of (R)-a-Methylbenzylamine 80
2.4.3 Analytical 82
2.4.4 Conclusion 82
References 82
2.5 Asymmetric Synthesis of L-3-Hydroxyadamantylglycine Using Branched Chain Aminotransferase 83
2.5.1 Procedure: Preparation of L-3-Hydroxyadamantylglycine
(2-(3-Hydroxy-1-Adamantyl)-(2S)-Amino Ethanoic Acid) (L-HAG) 84
2.5.2 Conclusion 85
References 86
2.6 Asymmetric Reduction of Aryl Imines Using Candida parapsilosis ATCC 7330 87
2.6.1 Procedure 1: Asymmetric Reduction of (E)-N- (1-Phenylethylidene)Benzenamine 1a Using Whole Cells of Candida parapsilosis ATCC 7330 87
2.6.2 Spectral Data for Compounds 2b, 5b and 6b 89
2.6.3 Conclusion 90
References 90
3 Enoate Reductases for Reduction of Electron Deficient Alkenes 91
3.1 Asymmetric Bioreduction of Activated Alkenes Using Ene-Reductases from the Old Yellow Enzyme Family 91
3.1.1 Procedure 1: Organic Solvent Effect in the Asymmetric Synthesis of the Olfactory Compounds Lysmeral and Helional93
3.1.2 Procedure 2: Protecting Group Effect in the Asymmetric
Synthesis of the Chiral Pharmaceutical Building Block `Roche Ester` 96
3.1.3 Procedure 3: Cofactor Regeneration System Effect in the Asymmetric Synthesis of (6R)-Levodione, a Precursor of Actinol 97
3.1.4 Procedure 4: Substrate Structure/Stereochemistry and Enzyme Effects in the Asymmetric Synthesis of Dicarboxylic Acid Esters 98
References 99
3.2 Efficient Baker`s Yeast Mediated Reduction with Substrate/Product Absorption on XAD Resins: Synthesis of (S)-2-Alkoxy-3-Aryl-1-Propanols 100
3.2.1 Baker`s Yeast Mediated Synthesis of (S)-2-Alkoxy-3- (4-Methoxyphenyl)-1-Propanols 101
3.2.2 Conclusion 103
References and Notes 104
3.3 Asymmetric Reduction of (4S)-(þ)-Carvone Catalyzed by Enoate Reductases (ERs) Expressed by Non-Conventional Yeast (NCY) Whole Cells 104
3.3.1 Materials and Equipment 105
3.3.2 Procedure 106
3.3.3 Analytical Methods 107
3.3.4 Conclusion 107
References and Notes 108
3.4 Preparation of Enantiomerically Pure Citronellal Enantiomers Using Alkene Reductases 108
3.4.1 Materials and Equipment 109
3.4.2 Procedure 110
3.4.3 Analytical Methods 112
3.4.4 Conclusion 112
References and Notes 112
3.5 Highly Enantiomeric Hydrogenation of C-C Double Bond of
Methylated N-Phenyl and N-Phenylalkylmaleimides by Aspergillus fumigatus 113
3.5.1 Biocatalytic Synthesis of Enantiomeric Pure 2-Methyl- and 2,3-Dimethyl- N-Phenyl and N-Phenylalkyl Succinimides 113
3.5.2 Product Analysis 115
3.5.3 Conclusion 118
References and Notes 119
4 Industrial Carbonyl Reduction 121
4.1 Bioreduction Using Immobilized Carbonyl Reductase Technology 122
4.1.1 Materials and Equipment 122
4.1.2 Procedure 123
4.1.3 Conclusion 124
References 124
4.2 Preparative Ketoreductase-Catalyzed Kinetic Resolution of a Racemic Aldehyde 124
4.2.1 2-L Scale Procedure 125
4.2.2 Conclusions 126
References 127
4.3 Enzymatic reduction of 2,6-dichloro-3-fluoro-acetophenone to produce (S)-1-(2,6-dichloro-3-fluorophenyl)ethanol 127
4.3.1 Procedure: Preparation of (1S)-1-(2,6-dichloro-3-fluorophenyl) ethanol (2) 128
4.3.2 Conclusion 130
References and Notes 130
4.4 Preparative Scale Production of Poorly Soluble Chiral Alcohol Intermediate for Montelukast 130
4.4.1 1-L Scale Procedure 131
4.4.2 Conclusions 132
References 133
5 Regio- and Stereoselective Hydroxylation 135
5.1 Engineering of an Amycolatopisis orientalis P450 Compactin Hydroxylase into a Pravastatin Synthase by Changing the Stereospecificity of the Enzyme 136
5.1.1 General Materials and Strains 136
5.1.2 Procedure 1: Generation of an Error Prone Library of Amycolatopsis orientalis P450 Hydroxylase 137
5.1.3 Procedure 2: Screening of the Error Prone Library for Improved Pravastatin: epi-Pravastatin Conversion Ratio 138
5.1.4 Procedure 3: Construction and Screening of the Second Generation Library Consisting of Site Saturation and Shuffling Approaches 141
5.1.5 Conclusion 143
References 143
5.2 Recombinant Human Cytochrome P450 Enzymes Expressed in Escherichia coli as Whole Cell Biocatalysts: Preparative Synthesis of Oxidized Metabolites of an mGlu5 Receptor Antagonist 144
5.2.1 Procedure 1: Screening of 14 rec. h. CYP-Isoforms for Biocatalyst Selection 145
5.2.2 Procedure 2: Propagation of E. coli JM109 Expressing rec.h. CYP3A4 and rec. h. P450 Reductase and Preparation of a Cell Suspension (Biocatalyst Production) 146
5.2.3 Procedure 3: Biotransformation with E. coli JM109 Expressing rec. h. CYP3A4 plus rec. h. P450 Reductase and Metabolite Purification 150
5.2.4 Conclusion 152
References and Notes 152
5.3 Alpha-Keto Biooxidation using Cunninghamella echinulata (DSM 63356) 153
5.3.1 Materials and Equipment 153
5.3.2 Procedure 154
5.3.3 Conclusion 156
References 156
5.4 Aromatic Hydroxylation: Preparation of 3,4-Dihydroxyphenylacetic Acid 156
5.4.1 Preparation of 3,4-Dihydroxyphenylacetic Acid 157
5.4.2 Analytical Methods 158
5.4.3 Conclusion 159
References and Notes 159
5.5 Regioselective Aromatic Hydroxylation of Quinaldine Using
Living Pseudomonas putida Cells Containing Quinaldine 4-Oxidase 159
5.5.1 Biocatalytic Hydroxylation of Quinaldine by Quinaldine
4-Oxidase 160
5.5.2 Analytical Methods 162
5.5.3 Product Isolation 162
5.5.4 Conclusion 163
References 163
5.6 Regioselective Preparation of 5-Hydroxypropranolol with aFungal Peroxygenase 164
5.6.1 Materials and Equipment 164
5.6.2 Procedure 165
5.6.3 Conclusion 165
References 165
5.7 Microbial Conversion of b-Myrcene to Geraniol by a Strain of Rhodococcus 165
5.7.1 Procedure 1: Growth of the Bacterium Rhodococcus erythropolis NCIMB 14574 on b-Myrcene 166
5.7.2 Procedure 2: Biotransformation of b-Myrcene to Geraniol by Rhodococcus erythropolis NCIMB 14574 167
5.7.3 Analysis 167
5.7.4 Conclusion 168
References and Notes 168
6 Oxidation of Alcohols 169
6.1 Preparative Method for the Enzymatic Synthesis of 5-Ketogluconic Acid and its Isolation 169
6.1.1 Procedure for the Preparation of 5-KGA 170
6.1.2 Conclusion 171
References 171
6.2 Selective Enzymatic Oxidation of Atropisomeric Diaryl Ethers by Oxidation with Oxygen and Catalytic Galactose Oxidase M3-5 172
6.2.1 Procedure: Enzymatic Desymmetrization of an Atropisomeric Diaryl Ether 172
6.2.2 Conclusion 175
References 175
6.3 Kinetic Resolution of Chiral Secondary Alcohols by Oxidation with Oxygen and Catalytic Galactose Oxidase M3-5 175
6.3.1 Procedure 1: Preparation of Galactose Oxidase (GOase) and Purification 175
6.3.2 Procedure 2: Enzymatic Kinetic Resolution of Chiral Secondary Alcohols 177
References 178
6.4 ADH Catalyzed Oxidation of Sec-Alcohols Using Molecular Oxygen 178
6.4.1 Materials and Equipment 179
6.4.2 Procedure 179
6.4.3 Conclusion 180
References 181
6.5 Irreversible Non-Enantioselective Oxidation of Secondary Alcohols Using Sphingobium ADH and Chloroacetone as Oxidant 181
6.5.1 Materials and Equipment 181
6.5.2 Procedure 183
6.5.3 Conclusion 183
References 183
6.6 Chemoselective Oxidation of Primary Alcohols to Aldehydes 183
6.6.1 Materials and Equipment 183
6.6.2 Procedure 184
6.6.3 Analytics 184
6.6.4 Conclusions 185
References 185
7 Selective Oxidation 187
7.1 Enantioselective Biocatalytic Oxidative Desymmetrization of Substituted Pyrrolidines 188
7.1.1 Procedure 1: Preparation of the Biocatalyst 188
7.1.2 Procedure 2: Desymmetrization of Pyrrolidines 189
7.1.3 Procedure 3: Stereoselective Synthesis of the Amino Acid 191
7.1.4 Conclusion 192
References 192
7.2 Large Scale Baeyer-Villiger Monooxygenase-Catalyzed Conversion of (R,S)-3-phenylbutan-2-one 193
7.2.1 Procedure 1: Recombinant Expression of the Baeyer-Villiger Monooxygenase from Pseudomonas putida JD1 in Escherichia coli 193
7.2.2 Procedure 2: Biocatalytic Conversion of (R, S)-3-Phenylbutan-2-one 194
7.2.3 Conclusion 195
References 195
7.3 Synthesis of Optically Active 3-Alkyl-3-,4-dihydroioscoumarins
by Dynamic Kinetic Resolutions Catalyzed by a Baeyer-Villiger Monooxygenase 196
7.3.1 Procedure: Dynamic Kinetic Resolution Using M446G PAMO Cell Free Extract 197
7.3.2 Conclusion 198
References 199
7.4 Oxidative Cleavage of the B-Ring of (þ)-Catechin 199
7.4.1 Procedure: Biocatalytic Conversion of (þ)-Catechin (1) to Novel B-Ring Fission Lactones (2, 3) 199
7.4.2 Conclusion 202
References 202
7.5 18O-Isotopic Labeling in the Meta-Dioxygenase Cleavage of (þ)-Catechin B-Ring 202
7.5.1 Proposed Pathway for the Conversion of (þ)-Catechin (1)
to 18O-Labeled, Novel B-Ring Fission Lactones (2, 3) 203
7.5.2 H2 18O and 18O2 Labeling Experiments 204
7.5.3 Conclusion 206
References 206
7.6 Biocatalytic Cleavage of Alkenes with Oxygen and Trametes Hirsuta G FCC047 206
7.6.1 Procedure 1: Analytical Scale 206
7.6.2 Procedure 2: Preparative Scale 208
7.6.3 Conclusion 208
References 209
8 Industrial Hydrolases and Related Enzymes 211
8.1 Dynamic Kinetic Resolution of a-Halo Esters with Hydrolytic Enzymes and Sec-amine Bases 211
8.1.1 Materials and Equipment 212
8.1.2 Procedures 213
8.1.3 Analytical Methods Used for a-Chloroesters and Acids 214
8.1.4 Conclusion 214
References 214
8.2 Kinetic Resolution of an Amino Ester Using Supported Mucor Miehei Lipase (LipozymeRM IM) 215
8.2.1 Procedure 1: Resolution of Ester III 216
8.2.2 Procedure 2: Resolution of Ester I 217
8.2.3 Procedure 3: Recycling of (S)-Acid 218
8.2.4 Conclusion 219
References 219
8.3 Large Scale Synthesis of (S)-Allysine Ethylene Acetal via Amino Acylase Resolution 220
8.3.1 Materials 221
8.3.2 Procedure 221
8.3.3 Conclusion 222
References and Notes 222
8.4 Pilot-Scale Synthesis of (1R,2S,4S)-7-Oxabicyclo[2.2.1]heptan-2-exo-carboxylic Acid 222
8.4.1 Experimental 223
8.4.2 Conclusion 224
References 225
8.5 A Selective Lipase-Catalyzed Mono-Acetylation of a Diol Suitable for a Telescoped Synthetic Process 225
8.5.1 Procedure 227
8.5.2 Conclusion 227
References 228
8.6 A Protease-Mediated Hydrolytic Kinetic Resolution of an Atropisomeric Ester Operating Within an Unusually Narrow pH Window 228
8.6.1 Procedure 229
8.6.2 Conclusion 230
References 230
8.7 Asymmetric Synthesis of Quaternary Amino Acids from Simple Bis Nitriles Using a Dual Nitrile Hydratase/Amidase Biocatalyzed Reaction 231
8.7.1 Materials and Equipment 231
8.7.2 Procedures 232
8.7.3 Conclusion 234
References 235
8.8 Development of an Improved Immobilized CAL-B for the Enzymatic Resolution of a Key Intermediate to Odanacatib 235
8.8.1 Procedure 1: CAL-B Immobilization Procedure 236
8.8.2 Procedure 2: Batch Reactions 236
8.8.3 Procedure 3: Continuous Plug Flow Reactions 237
8.8.4 Conclusion 237
References 237
9 Transferases for Alkylation, Glycosylation and Phosphorylation 239
9.1 Industrial Production of Caffeic Acid-a-D-O-Glucoside 240
9.1.1 Procedure 1: Preparation of the Glucosyltransferase Enzyme 240
9.1.2 Procedure 2: Preparation of Caffeic Acid-a-D-O-Glucoside 241
9.1.3 Specification of the Product 242
9.1.4 Analytical Controls 242
9.1.5 Conclusion 243
9.2 Enzymatic Synthesis of 5-Methyluridine by Transglycosylation of Guanosine and Thymine 243
9.2.1 Procedure 1: Production of Biocatalysts 244
9.2.2 Procedure 2: Biocatalytic Production of 5-Methyluridine (5-MU) 245
9.2.3 Procedure 3: Isolation and Recovery of 5-MU 246
9.2.4 Conclusion 247
References 247
9.3 Preparation and Use of Sucrose Phosphorylase as Cross-Linked
Enzyme Aggregate (CLEA)248
9.3.1 Procedure 1: Production of Cellular Biomass 249
9.3.2 Procedure 2: Cell Lysis and Enzyme Purification 249
9.3.3 Procedure 3: Production of CLEAs 250
9.3.4 Procedure 4: Production of a-D-Glucose-1-phosphate 251
9.3.5 Analytical Data 251
9.3.6 Conclusion 252
References 252
9.4 Enzymatic Synthesis of Phosphorylated Carbohydrates and Alcohols 252
9.4.1 Procedure: Preparative Synthesis of G6P 253
9.4.2 Conclusion 254
References 254
9.5 Biocatalyzed Synthesis of Chiral O-Phosphorylated Derivative of 2-Hydroxy-2-phenylethanephosphonate 255
9.5.1 Biotransformation of Diethyl 2-oxo-2-phenylethanephosphonate 255
9.5.2 Conclusion 258
References and Notes 258
9.6 Stereospecific Synthesis of Aszonalenins by using Two Recombinant Prenyltransferases 258
9.6.1 Procedure 1: Preparation of the Prenyltransferases CdpNPT and AnaPT 259
9.6.2 Procedure 2: Preparative Synthesis and Structural Elucidation of Aszonalenins 261
9.6.3 Conclusion 263
References 263
9.7 Enzymatic Friedel-Crafts Alkylation Catalyzed by S-Adenosyl-L-methionine Dependent Methyltransferase 263
9.7.1 Procedure 1: Crotyl-S-adenosyl-L-homocysteine triflate 3 264
9.7.2 Procedure 2: N-(8-Crotyl-4,7-dihydroxy-2-oxo-2H-chromen-3-yl)-1H-pyrrole-2-carboxamide 265
9.7.3 Conclusion 267
References 267
10 C-C Bond Formation and Decarboxylation 269
10.1 Enzymatic, Stereoselective Synthesis of (S)-Norcoclaurine 270
10.1.1 Procedure 1: Synthesis of 4-Hydroxyphenylacetaldehyde 270
10.1.2 Procedure 2: Synthesis of (S)-Norcoclaurine 271
10.1.3 Conclusion 273
References 273
10.2 Preparation of Non-Natural Tyrosine Derivatives from Pyruvate and Phenol Derivatives 273
10.2.1 Procedure for the Preparation of L-3-Methoxytyrosine 274
10.2.2 Conclusion 275
References 275
10.3 Enzymatic a-Decarboxylation of L-Glutamic Acid in the Production of Biobased Chemicals 275
10.3.1 Procedure 1: GAD Immobilization 276
10.3.2 Procedure 2: Product Quantification by HPLC 277
10.3.3 Procedure 3: GAD Activity Assay 278
10.3.4 Procedure 4: GAD Stability Assay 278
10.3.5 Conclusion 280
References 280
10.4 Asymmetric Decarboxylation of Arylmalonates and Racemization of Profens by Arylmalonate Decarboxylase and its Variants 280
10.4.1 Procedure 1: Asymmetric Decarboxylation of Arylmalonate 281
10.4.2 Procedure 2: Enzymatic Racemization of Profens 283
10.4.3 Conclusion 285
References 286
10.5 Improved Enzymatic Preparation of 1-Deoxy-D-xylulose 5-Phosphate 286
10.5.1 Synthesis of DXP 288
10.5.2 Purification of DXP 288
10.5.3 Conclusion 289
References 289
10.6 On the Use of 2-Methyltetrahydrofuran (2-MeTHF) as Bio-Based (Co-) Solvent in Biotransformations 290
10.6.1 The Quest for Efficient and Bio-Based (Co-) Solvents 290
10.6.2 Case Study 1: Alcohol Dehydrogenase Catalyzed Enantioselective Ketone Reduction using 2-MeTHF as (Co-) Solvent 291
10.6.3 Case Study 2: Benzaldehyde Lyase (BAL) Catalyzed Enantioselective C-C Bond Formation using 2-MeTHF as (Co-) Solvent 293
10.6.4 Concluding Remarks 296
Acknowledgements 296
References 297
10.7 The Lipase-Catalyzed Asymmetric Michael Addition of Thienyl Nitroolefin to Acetylacetone 297
10.7.1 Procedure 1: The Lipozyme TLIM Catalyzed Michael Addition of Thienyl Nitroolefin to Acetylacetone 298
10.7.2 Procedure 2: Regeneration and Reuse of Lipozyme TLIM 299
10.7.3 Conclusion 300
References 300
11 Halogenation/Dehalogenation/Heteroatom Oxidation 303
11.1 Preparation of Halogenated Molecules by a Fungal Flavin-Dependent Halogenase Heterologously Expressed in Escherichia coli 305
11.1.1 Whole-Cell Biocatalytic Halogenation of Dihydroresorcylide 305
11.1.2 Conclusion 307
References and Notes 307
11.2 Preparation of Optically Pure Haloalkanes and Alcohols by Kinetic Resolution using Haloalkane Dehalogenases 307
11.2.1 Procedure 1: Kinetic Resolution of a-Bromoesters and b-Bromoalkanes 308
11.2.2 Procedure 2: Gram-Scale Synthesis of (S)-2-Bromopentane 309
11.2.3 Conclusions 312
Acknowledgements 312
References 313
11.3 Preparation of Enantiopure Sulfoxides by Enantioselective Oxidation with Whole Cells of Rhodococcus sp. ECU0066 313
11.3.1 Procedure: Preparation of (S)-Phenyl Methyl Sulfoxide 1a 314
11.3.2 Conclusion 316
References and Notes 316
11.4 Kinetic Resolution of an Insecticidal Dithiophosphate by Chloroperoxidase Catalyzed Oxidation of the Thiophosphoryl Group 316
11.4.1 Procedure: Kinetic Resolution of Racemic Dithiophosphate 1 by Oxidation with CPO/H2O2 System 317
11.4.2 Conclusion 318
References 318
12 Tandem and Sequencial Multi-Enzymatic Syntheses 319
12.1 Production of Isorhamnetin 3-O-Glucoside in Escherichia coli using Engineered Glycosyltransferase 319
12.1.1 Materials and Equipment 320
12.1.2 Procedure 322
12.1.3 Analytical Methods 322
12.1.4 Conclusion 322
References and Notes 322
12.2 Multienzymatic Preparation of ()-3-(Oxiran-2-yl)Benzoic Acid 323
12.2.1 Materials and Equipment 323
12.2.2 Procedure 324
12.2.3 Work Up Procedure 326
12.2.4 Analytical Methods 326
12.2.5 Conclusion 326
References and Notes 327
12.3 Enzymatic Synthesis of Carbohydrates from Dihydroxyacetone and Aldehydes by a One Pot Enzyme Cascade Reaction 327
12.3.1 Procedure: Synthesis of 5,6-Dideoxy-D-threo-2-hexulose (3S,4R) 328
12.3.2 Conclusion 329
References 329
12.4 Aldolase Based Multi-Enzyme System for Carbon-Carbon Bond Formation 329
12.4.1 Procedure 1: One Pot/One Step 330
12.4.2 Procedure 2: One Pot/Two Steps 331
12.4.3 Analytical Data for the Products from Aldehyde 13 336
12.4.4 Conclusion 336
Acknowledgements 337
References 337
12.5 Tandem Biocatalytic Process for the Kinetic Resolution of b-Phenylalanine and its Analogs 337
12.5.1 Procedure 1: Expression and Purification of a Mutated Phenylalanine Aminomutase (PAM-Q319M) and Phenylalanine Ammonia Lyase (PAL) 338
12.5.2 Procedure 2: Kinetic Resolution of Racemic b-Phenylalanine 339
12.5.3 Conclusion 340
References 341
12.6 A Chemoenzymatic Synthesis of a Deoxy Sugar Ester of N-Boc-Protected L-Tyrosine 341
12.6.1 Procedure 1: The O-Alkylation of Carboxylic Acid and Lipase-Catalyzed Deacetylation (Performed as a "One-Pot Synthesis") 342
12.6.2 Procedure 2: Lipase-Catalyzed Acetylation of Hemiacetal 3 343
12.6.3 Procedure 3: Lipase-Catalyzed Deacetylation of Compound 4 344
12.6.4 Conclusion 345
References 345
12.7 Electrochemical Systems for the Recovery of Succinic Acid from Fermentations 345
12.7.1 Materials and Equipment (Fermentation) 346
12.7.2 Analytical Method 346
12.7.3 Culture of Actinobacillus succinogenes 346
12.7.4 Fermentation Media 347
12.7.5 Fermentation 347
12.7.6 Work Up Electrodialysis Conditions 348
12.7.7 Conclusion 351
References and Notes 351
Index
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Whittall, John, Practical Methods for Biocatalysis and Biotransformations 2
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