Practical Methods for Biocatalysis and Biotransformations 3 (eBook, PDF)
Redaktion: Whittall, John; Kroutil, Wolfgang; Sutton, Peter W.
Practical Methods for Biocatalysis and Biotransformations 3 (eBook, PDF)
Redaktion: Whittall, John; Kroutil, Wolfgang; Sutton, Peter W.
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Biocatalysts are increasingly used by chemists engaged in fine chemical synthesis within both industry and academia. Today, there exists a huge choice of high-tech enzymes and whole cell biocatalysts, which add enormously to the repertoire of synthetic possibilities. Practical Methods for Biocatalysis and Biotransformations 3 will be a companion book to Practical Methods for Biocatalysis and Biotransformations (2009) and Practical Methods for Biocatalysis and Biotransformations 2 (2012). Following the successful format of the two volumes, it will be a "how-to" guide focusing on commercially…mehr
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- Produktdetails
- Verlag: John Wiley & Sons
- Seitenzahl: 320
- Erscheinungstermin: 29. März 2016
- Englisch
- ISBN-13: 9781118696286
- Artikelnr.: 44782033
- Verlag: John Wiley & Sons
- Seitenzahl: 320
- Erscheinungstermin: 29. März 2016
- Englisch
- ISBN-13: 9781118696286
- Artikelnr.: 44782033
and Pilot
Scale Biocatalysis for Chemical Synthesis 1 1.1 Introduction 1 1.2 Process Intensification and Proposed Scale
Up Concept 2 1.3 Enabling Technologies 5 1.4 Enhancing Technologies 20 1.5 Conclusion 28 References 28 2 Cytochrome P450 (CYP) Progress in Biocatalysis for Synthetic Organic Chemistry 31 2.1 Introduction 31 2.2 CYP Development 32 2.3 Recent Developments 34 2.4 Conclusion 41 References 41 3 Use of Hydrolases and Related Enzymes for Synthesis 43 3.1 Continuous
Flow Reactor
Based Enzymatic Synthesis of Phosphorylated Compounds on a Large Scale 43 3.2 Deracemization of sec
Alcohols via Enantio
Convergent Hydrolysis of rac
Sulfate Esters 45 3.3 Dynamic Kinetic Resolution of a Primary Amine by an Efficient Bifunctional Pd
CALB Hybrid Catalyst. A Metalloenzyme Mimic for Enhanced Cooperative Catalysis 50 3.4 Highly Efficient DKR of Secondary 1
Phenylethanol Derivatives Using a Low
Cost Solid Super Acid as Racemization Catalyst 53 3.5 Identification of New Biocatalysts for the Enantioselective Conversion of Tertiary Alcohols 58 3.6 Enzyme
Catalyzed Hydrolysis of Bicycloheptane Diester to Monoester 60 3.7 Double Mutant Lipase with Enhanced Activity and Enantioselectivity for Bulky Secondary Alcohols 64 3.8 Stereoselective Synthesis of ß
Amino Acids by Hydrolysis of an Aryl
Substituted Dihydropyrimidine by Hydantoinases 68 References 72 4 Non
Redox Lyases and Transferases for C
C, C
O, C
S, and C
N Bond Formation 75 4.1 Regioselective Enzymatic Carboxylation of Phenols and Hydroxystyrenes Employing Co
Factor
Independent Decarboxylases 75 4.2 Stetter Reactions Catalyzed by Thiamine Diphosphate
Dependent Enzymes 81 4.3 Asymmetric Michael
Type Additions of Acetaldehyde to Nitroolefins Catalyzed by 4
Oxalocrotonate Tautomerase (4
OT) Yielding Valuable gamma
Nitroaldehydes 85 4.4 Michael
Type Addition of Aldehydes to ß
Nitrostyrenes by Whole Cells of Escherichia coli Expressing 4
Oxalocrotonate Tautomerase (4
OT) 91 4.5 Norcoclaurine Synthases for the Biocatalytic Synthesis of Tetrahydroisoquinolines 95 4.6 Streptavidin
Based Artificial Metallo
Annulase for the Enantioselective Synthesis of Dihydroisoquinolones 101 4.7 Regiospecific Benzylation of Tryptophan and Derivatives Catalyzed by a Fungal Dimethylallyl Transferase 102 4.8 Enantioselective Michael Addition of Water Using Rhodococcus Rhodochrous ATCC 17895 106 4.9 Sulfation of Various Compounds by an Arylsulfotransferase from Desulfitobacterium hafniense and Synthesis of 17ß
Estradiol
3
Sulfate 111 4.10 Asymmetric Synthesis of Cyclopropanes and Benzosultams via Enzyme
Catalyzed Carbenoid and Nitrenoid Transfer in E. coli Whole Cells 113 4.11 Biocatalytic Production of Novel Glycolipids 118 4.12 Enzymatic Synthesis of 8
Aza
and 8
Aza
7
Deazapurine 2¿
Deoxyribonucleosides 124 4.13 Phenylalanine Ammonia Lyase
Catalyzed Asymmetric Hydroamination for the Synthesis of L
Amino Acids 128 References 130 5 Oxidations 135 5.1 Semi
Preparative
Scale Drug Metabolite Synthesis with Human Flavin Monooxygenases 135 5.2 Biobased Synthesis of Industrially Relevant Nitriles by Selective Oxidative Decarboxylation of Amino Acids by Vanadium Chloroperoxidase 139 5.3 Terminal Oxygenation of Fatty Acids by a CYP153A Fusion Construct Heterologously Expressed in E. coli 142 5.4 Enantioselective Oxidative C
C Bond Formation in Isoquinoline Alkaloids Employing the Berberine Bridge Enzyme 144 5.5 Oxidation of Aldehydes Using Alcohol Dehydrogenases 148 5.6 MAO
Catalyzed Deracemization of Racemic Amines for the Synthesis of Pharmaceutical Building Blocks 150 5.7 Synthesis of (S)
Amines by Chemo
Enzymatic Deracemization Using an (R)
Selective Amine Oxidase 153 5.8 Selective Oxidation of Diols into Lactones under Aerobic Conditions Using a Laccase
TEMPO Catalytic System in Aqueous Medium 156 References 160 6 Reductions 163 6.1 Tetrahydroxynaphthalene Reductase: Broad Substrate Range of an NADPH
Dependent Oxidoreductase Involved in Reductive Asymmetric Naphthol Dearomatization 163 6.2 Chemoenzymatic Synthesis of Diastereo
and Enantiomerically Pure 2,6
Disubstituted Piperidines via Regioselective Monoamination of 1,5
Diketones 167 6.3 Asymmetric Amination of Ketones Employing omega
TAs in Organic Solvents 171 6.4 Stereoselective Synthesis of (R)
Profen Derivatives by the Enoate Reductase YqjM 176 6.5 Productivity Improvement of the Bioreduction of alpha,ß
Unsaturated Aldehydes by Coupling of the In Situ Substrate Feeding Product Removal (SFPR) Strategy with Isolated Enzymes 181 6.6 Reduction of Imines by Recombinant Whole
Cell E. coli Biocatalysts Expressing Imine Reductases (IREDs) 186 References 191 7 Halogenation and Dehalogenation 193 7.1 Site
Directed Mutagenesis Changes the Regioselectivity of the Tryptophan 7
Halogenase PrnA 193 7.2 Controlling Enantioselectivity of Halohydrin Dehalogenase from Arthrobacter sp. Strain AD2, Revealed by Structure
Guided Directed Evolution 197 7.3 Enzymatic Production of Chlorothymol and its Derivatives by Halogenation of the Phenolic Monoterpenes Thymol and Carvacrol with Chloroperoxidase 201 7.4 Halogenation of Non
Activated Fatty Acyl Groups by a Trifunctional Non
Heme Fe(II)
Dependent Halogenase 204 References 211 8 Cascade Reactions 213 8.1 Synthetic Cascades via a Combination of Artificial Metalloenzymes with Monoamine Oxidases (MAO
Ns) 213 8.2 Amination of Primary Alcohols via a Redox
Neutral Biocascade 215 8.3 Biocatalytic Synthesis of a Diketobornane as a Building Block for Bifunctional Camphor Derivatives 218 8.4 Three Enzyme
Catalyzed Redox Cascade for the Production of a Carvo
Lactone 222 8.5 Preparation of Homoallylic Alcohols via a Chemoenzymatic One
Pot Oxidation
Allylation Cascade 226 8.6 Cascade Biotransformations via Enantioselective Reduction, Oxidation, and Hydrolysis: Preparation of (R)
delta
Lactones from 2
Alkylidenecyclopentanones 230 8.7 One
Pot Tandem Enzymatic Reactions for Efficient Biocatalytic Synthesis of D
Fructose
6
Phosphate and Analogs 232 8.8 Efficient One
Pot Tandem Biocatalytic Process for a Valuable Phosphorylated C8 D
Ketose: D
Glycero
D
Altro
2
Octulose 8
Phosphate 239 8.9 Chemoenzymatic Synthesis of (S)
1,2,3,4
Tetrahydroisoquinoline
3
Carboxylic Acid by PAL
Mediated Amination and Pictet
Spengler Cyclization 243 8.10 omega
TA/MAO Cascade for the Regio
and Stereoselective Synthesis of Chiral 2,5
Disubstituted Pyrrolidines 246 References 249 9 Biocatalysis for Industrial Process Development 253 9.1 Efficient Synthesis of (S)
1
(5
Fluoropyrimidin
2
yl)ethylamine Hydrochloride Salt Using an omega
Transaminase Biocatalyst in a Two
Phase System 253 9.2 Preparative
scale Production of a Chiral, Bicyclic Proline Analog Intermediate for Boceprevir 257 9.3 Focused Carbonyl Reductase Screening for Rapid Gram Supply of Highly Enantioenriched Secondary Alcohol Libraries 260 9.4 A Rapid, Inexpensive and Colorimetric High
throughput Assay Format for Screening Commercial Ketoreductase Panels, Providing Indication of Substrate Scope, Co
factor Specificity and Enantioselectivity 266 9.5 Stereoselective Production of (R)
3
quinuclidinol Using Recombinant Escherichia coli Whole Cells Overexpressing 3
Quinuclidinone Reductase and a Co
factor Regeneration System 273 9.6 Preparation of N
Boc
D
Serine Using a Coupled D
Acylase/Racemase Enzyme System 275 9.7 Scale
up of a Biocatalytic Oxidase in a Dynamically Mixed Tubular Flow Reactor 279 References 282 Index 285
and Pilot
Scale Biocatalysis for Chemical Synthesis 1 1.1 Introduction 1 1.2 Process Intensification and Proposed Scale
Up Concept 2 1.3 Enabling Technologies 5 1.4 Enhancing Technologies 20 1.5 Conclusion 28 References 28 2 Cytochrome P450 (CYP) Progress in Biocatalysis for Synthetic Organic Chemistry 31 2.1 Introduction 31 2.2 CYP Development 32 2.3 Recent Developments 34 2.4 Conclusion 41 References 41 3 Use of Hydrolases and Related Enzymes for Synthesis 43 3.1 Continuous
Flow Reactor
Based Enzymatic Synthesis of Phosphorylated Compounds on a Large Scale 43 3.2 Deracemization of sec
Alcohols via Enantio
Convergent Hydrolysis of rac
Sulfate Esters 45 3.3 Dynamic Kinetic Resolution of a Primary Amine by an Efficient Bifunctional Pd
CALB Hybrid Catalyst. A Metalloenzyme Mimic for Enhanced Cooperative Catalysis 50 3.4 Highly Efficient DKR of Secondary 1
Phenylethanol Derivatives Using a Low
Cost Solid Super Acid as Racemization Catalyst 53 3.5 Identification of New Biocatalysts for the Enantioselective Conversion of Tertiary Alcohols 58 3.6 Enzyme
Catalyzed Hydrolysis of Bicycloheptane Diester to Monoester 60 3.7 Double Mutant Lipase with Enhanced Activity and Enantioselectivity for Bulky Secondary Alcohols 64 3.8 Stereoselective Synthesis of ß
Amino Acids by Hydrolysis of an Aryl
Substituted Dihydropyrimidine by Hydantoinases 68 References 72 4 Non
Redox Lyases and Transferases for C
C, C
O, C
S, and C
N Bond Formation 75 4.1 Regioselective Enzymatic Carboxylation of Phenols and Hydroxystyrenes Employing Co
Factor
Independent Decarboxylases 75 4.2 Stetter Reactions Catalyzed by Thiamine Diphosphate
Dependent Enzymes 81 4.3 Asymmetric Michael
Type Additions of Acetaldehyde to Nitroolefins Catalyzed by 4
Oxalocrotonate Tautomerase (4
OT) Yielding Valuable gamma
Nitroaldehydes 85 4.4 Michael
Type Addition of Aldehydes to ß
Nitrostyrenes by Whole Cells of Escherichia coli Expressing 4
Oxalocrotonate Tautomerase (4
OT) 91 4.5 Norcoclaurine Synthases for the Biocatalytic Synthesis of Tetrahydroisoquinolines 95 4.6 Streptavidin
Based Artificial Metallo
Annulase for the Enantioselective Synthesis of Dihydroisoquinolones 101 4.7 Regiospecific Benzylation of Tryptophan and Derivatives Catalyzed by a Fungal Dimethylallyl Transferase 102 4.8 Enantioselective Michael Addition of Water Using Rhodococcus Rhodochrous ATCC 17895 106 4.9 Sulfation of Various Compounds by an Arylsulfotransferase from Desulfitobacterium hafniense and Synthesis of 17ß
Estradiol
3
Sulfate 111 4.10 Asymmetric Synthesis of Cyclopropanes and Benzosultams via Enzyme
Catalyzed Carbenoid and Nitrenoid Transfer in E. coli Whole Cells 113 4.11 Biocatalytic Production of Novel Glycolipids 118 4.12 Enzymatic Synthesis of 8
Aza
and 8
Aza
7
Deazapurine 2¿
Deoxyribonucleosides 124 4.13 Phenylalanine Ammonia Lyase
Catalyzed Asymmetric Hydroamination for the Synthesis of L
Amino Acids 128 References 130 5 Oxidations 135 5.1 Semi
Preparative
Scale Drug Metabolite Synthesis with Human Flavin Monooxygenases 135 5.2 Biobased Synthesis of Industrially Relevant Nitriles by Selective Oxidative Decarboxylation of Amino Acids by Vanadium Chloroperoxidase 139 5.3 Terminal Oxygenation of Fatty Acids by a CYP153A Fusion Construct Heterologously Expressed in E. coli 142 5.4 Enantioselective Oxidative C
C Bond Formation in Isoquinoline Alkaloids Employing the Berberine Bridge Enzyme 144 5.5 Oxidation of Aldehydes Using Alcohol Dehydrogenases 148 5.6 MAO
Catalyzed Deracemization of Racemic Amines for the Synthesis of Pharmaceutical Building Blocks 150 5.7 Synthesis of (S)
Amines by Chemo
Enzymatic Deracemization Using an (R)
Selective Amine Oxidase 153 5.8 Selective Oxidation of Diols into Lactones under Aerobic Conditions Using a Laccase
TEMPO Catalytic System in Aqueous Medium 156 References 160 6 Reductions 163 6.1 Tetrahydroxynaphthalene Reductase: Broad Substrate Range of an NADPH
Dependent Oxidoreductase Involved in Reductive Asymmetric Naphthol Dearomatization 163 6.2 Chemoenzymatic Synthesis of Diastereo
and Enantiomerically Pure 2,6
Disubstituted Piperidines via Regioselective Monoamination of 1,5
Diketones 167 6.3 Asymmetric Amination of Ketones Employing omega
TAs in Organic Solvents 171 6.4 Stereoselective Synthesis of (R)
Profen Derivatives by the Enoate Reductase YqjM 176 6.5 Productivity Improvement of the Bioreduction of alpha,ß
Unsaturated Aldehydes by Coupling of the In Situ Substrate Feeding Product Removal (SFPR) Strategy with Isolated Enzymes 181 6.6 Reduction of Imines by Recombinant Whole
Cell E. coli Biocatalysts Expressing Imine Reductases (IREDs) 186 References 191 7 Halogenation and Dehalogenation 193 7.1 Site
Directed Mutagenesis Changes the Regioselectivity of the Tryptophan 7
Halogenase PrnA 193 7.2 Controlling Enantioselectivity of Halohydrin Dehalogenase from Arthrobacter sp. Strain AD2, Revealed by Structure
Guided Directed Evolution 197 7.3 Enzymatic Production of Chlorothymol and its Derivatives by Halogenation of the Phenolic Monoterpenes Thymol and Carvacrol with Chloroperoxidase 201 7.4 Halogenation of Non
Activated Fatty Acyl Groups by a Trifunctional Non
Heme Fe(II)
Dependent Halogenase 204 References 211 8 Cascade Reactions 213 8.1 Synthetic Cascades via a Combination of Artificial Metalloenzymes with Monoamine Oxidases (MAO
Ns) 213 8.2 Amination of Primary Alcohols via a Redox
Neutral Biocascade 215 8.3 Biocatalytic Synthesis of a Diketobornane as a Building Block for Bifunctional Camphor Derivatives 218 8.4 Three Enzyme
Catalyzed Redox Cascade for the Production of a Carvo
Lactone 222 8.5 Preparation of Homoallylic Alcohols via a Chemoenzymatic One
Pot Oxidation
Allylation Cascade 226 8.6 Cascade Biotransformations via Enantioselective Reduction, Oxidation, and Hydrolysis: Preparation of (R)
delta
Lactones from 2
Alkylidenecyclopentanones 230 8.7 One
Pot Tandem Enzymatic Reactions for Efficient Biocatalytic Synthesis of D
Fructose
6
Phosphate and Analogs 232 8.8 Efficient One
Pot Tandem Biocatalytic Process for a Valuable Phosphorylated C8 D
Ketose: D
Glycero
D
Altro
2
Octulose 8
Phosphate 239 8.9 Chemoenzymatic Synthesis of (S)
1,2,3,4
Tetrahydroisoquinoline
3
Carboxylic Acid by PAL
Mediated Amination and Pictet
Spengler Cyclization 243 8.10 omega
TA/MAO Cascade for the Regio
and Stereoselective Synthesis of Chiral 2,5
Disubstituted Pyrrolidines 246 References 249 9 Biocatalysis for Industrial Process Development 253 9.1 Efficient Synthesis of (S)
1
(5
Fluoropyrimidin
2
yl)ethylamine Hydrochloride Salt Using an omega
Transaminase Biocatalyst in a Two
Phase System 253 9.2 Preparative
scale Production of a Chiral, Bicyclic Proline Analog Intermediate for Boceprevir 257 9.3 Focused Carbonyl Reductase Screening for Rapid Gram Supply of Highly Enantioenriched Secondary Alcohol Libraries 260 9.4 A Rapid, Inexpensive and Colorimetric High
throughput Assay Format for Screening Commercial Ketoreductase Panels, Providing Indication of Substrate Scope, Co
factor Specificity and Enantioselectivity 266 9.5 Stereoselective Production of (R)
3
quinuclidinol Using Recombinant Escherichia coli Whole Cells Overexpressing 3
Quinuclidinone Reductase and a Co
factor Regeneration System 273 9.6 Preparation of N
Boc
D
Serine Using a Coupled D
Acylase/Racemase Enzyme System 275 9.7 Scale
up of a Biocatalytic Oxidase in a Dynamically Mixed Tubular Flow Reactor 279 References 282 Index 285