Modern biocatalysis: stereoselective and environmentally friendly reactions
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| Sprache: | English |
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Weinheim
WILEY-VCH
2009
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| Beschreibung: | XXIII, 375 S. Ill., graph. Darst. |
| ISBN: | 9783527320714 |
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| 245 | 1 | 0 | |a Modern biocatalysis |b stereoselective and environmentally friendly reactions |c ed. by Wolf-Dieter Fessner ... |
| 264 | 1 | |a Weinheim |b WILEY-VCH |c 2009 | |
| 300 | |a XXIII, 375 S. |b Ill., graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 4 | |a Biocatalysis | |
| 650 | 4 | |a Biotechnology |x methods | |
| 650 | 4 | |a Catalysis | |
| 650 | 4 | |a Enzymes |x Biotechnology | |
| 650 | 4 | |a Enzymes |x physiology | |
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Datensatz im Suchindex
| _version_ | 1805091766878076928 |
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| adam_text |
Titel: Modern biocatalysis
Autor: Fessner, Wolf-Dieter
Jahr: 2009
V
Contents
Preface XV
List of Contributors XVII
1 Fluorescence Assays for Biotransformations 1
Jean-Louis Reymond
1.1 Introduction 1
1.2 Alcohol Dehydrogenases (ADHs) and Aldolases 2
1.2.1 Chiral Fluorogenic ADH Substrates 2
1.2.2 Fluorogenic Aldolase Probes 3
1.2.3 Transaldolases and Transketolases 4
1.2.4 Enolase Probe 4
1.3 Lipases and Esterases 5
1.3.1 Assays on Solid Support 6
1.3.2 The Clips-O Substrates with Periodate 8
1.3.3 Esters of Fluorogenic Cyanohydrins and Hydroxyketones 9
1.3.4 Fluorogenic Acyloxymethyl Ethers 10
1.3.5 FRET-Lipase Probes 11
1.4 Other Hydrolases 11
1.4.1 Epoxide Hydrolases 11
1.4.2 Amidases and Proteases 13
1.4.3 Phosphatases 14
1.5 Baeyer-Villigerases 15
1.6 Conclusion 15
Acknowledgment 16
References 16
2 Immobilization as a Tool for Improving Enzymes 21
UlfHanefeld
2.1 Introduction 21
2.2 Adsorption/Electrostatic Interactions 22
2.2.1 Van der Waals Interactions 22
2.2.2 Hydrogen Bonds 25
Modem Biocatalysis: Stereosdective and Environmentally Friendly Reactions.
Edited by Wolf-Dieter Fessner and Thorleif Anthonsen
Copyright © 2009 WILEY-VCH Verlag GmbH Co. KGaA, Weinheim
ISBN: 978-3-527-32071-4
VI I Contents
2.2.3 Ionic Interactions 27
2.3 Encapsulation 31
2.4 Covalent Binding/Cross-linking 33
2.5 Conclusion 38
Acknowledgments 38
References 39
3 Continuous-flow MicroChannel Reactors with Surface-immobilized
Biocatalysts 43
Malene S. Thomsen and Bernd Nidetzky
3.1 Introduction 43
3.2 Biocatalytic Synthesis Using Microreaction Technology with Free and
Immobilized Enzymes 44
3.3 Novel Microfluidic Immobilized Enzyme Reactors 45
3.3.1 Microreactor Design 45
3.3.2 Enzyme Immobilization 47
3.4 Enzymatic Hydrolysis of Lactose 48
3.4.1 Catalytic Effectiveness of Immobilized CelB 48
3.4.2 Continuous Conversion of Lactose 48
3.5 Biocatalytic Process Intensification Using Microreaction
Technology 50
3.6 Conclusions and Outlook 51
Acknowledgements 52
References 52
4 Activity and Stability of Proteases in Hydrophilic Solvents 55
Lars Haastrup Pedersen, S'mXhuwaX Ritthitham, and Morten Kristensen
4.1 Introduction 55
4.2 Activity and Selectivity of Proteases in Synthesis of Carbohydrate Fatty
Acid Esters 56
4.3 Enzyme Stability and Conformation 59
4.4 Solvent Engineering 63
4.5 Conclusion 64
References 65
5 Importance of Enzyme Formulation for the Activity and
Enantioselectivity of Upases in Organic Solvents 67
Francesco Secundo
5.1 Introduction 67
5.2 Lipase Formulations and their Activity and Enantioselectivity in Neat
Organic Solvent 68
5.3 Why do Additives Affect the Activity and Enantioselectivity of Lipases
in Organic Solvent? 73
5.4 Conclusions 76
References 76
I
i
Contents VII
6 Direct Esterification with Dry Mycelia of Molds: a (Stereo)selective,
Mild and Efficient Method for Obtaining Structurally Diverse
Esters 79
Francesco Molinari, Diego Romano, Raffaella Gandolfi, Lucia Cardossi, Ulf
Hanefeld, Attilio Convert! and Patrizia Spizzo
6.1 Mycelia and Biotransformations in Organic Media 79
6.2 Screening and Microbiological Aspects 79
6.3 Production of Acetate 81
6.4 Stereoselective Esterifications of Racemic Alcohols 83
6.5 Stereoselective Esterifications of Racemic Carboxylic Acids 85
6.6 Partition Phenomena and Equilibrium of Esterification Reactions 88
6.7 Conclusions 91
References 91
7 Factors Affecting Enantioselectivity: Allosteric Effects 93
Elisabeth Egholrn Jacobsen and Thorleif Anthonsen
7.1 How to Provide Enantiopure Compounds 93
7.1.1 Kinetic Resolution of Racemic Mixtures Catalyzed by Enzymes 94
7.1.2 Absolute Configurations in Resolution 95
7.2 Factors Affecting the Enantiomeric Ratio E 96
7.2.1 Is the £-value Really Constant? 96
7.2.2 Influence of the Reaction Medium on the E-value 96
7.2.3 Influence of Enzyme Immobilization on the E-value 97
7.2.4 Enzyme Inhibition 97
7.2.5 Enantioselective Inhibition and Activation: Allosteric Effects 97
7.2.6 The E-value of CALB is Influenced by R-Alcohols 99
7.2.7 Is a Changing E Caused by the Slow or the Fast Enantiomer? 102
7.3 Asymmetrization of Prochiral Compounds 103
7.3.1 Asymmetrization of Prochiral Dicarboxylates: Single-Step
Process 103
7.3.2 Asymmetrization of Prochiral Diol: Double-Step Process 105
7.3.3 Is the e.e. Constant During Asymmetrization Reactions? 105
7.4 Conclusions 106
References 107
8 Kinetic Resolution of Sec-alcohol in Non-conventional Media 209
Maja Habulin, Mateja Primoiid and 2e\jko Knez
8.1 Introduction 209
8.2 SCFs-Replacement for Organic Solvents in Biocatalysis 111
8.3 Effect of Pressure 112
8.4 Effect of the Acyl Donor/Alcohol Molar Ratio 114
8.5 ILs-Solvents for Sustainable Technology in Biocatalysis 114
8.6 ILs, Based on the N, N'-Dialkylimidazolium Cations as Reaction
Media 116
8.7 I Ls/SCFs Biphasic Systems as Promising Media for Biocatalysis 117
VIII Contents
8.8 The [bmim][PF6]/SC-CO2 System as a Reaction Medium 117
8.9 Effect of Acyl Donor Concentration 119
8.10 Conclusion 120
References 120
9 Strategies for the Biocatalytic Lipophilization of Phenolic
Antioxidants 123
Maria H. Katsoura, Eleni Theodosiou, Haralambos Stamatis and
Fragiskos N. Kolisis
9.1 Introduction 123
9.2 Materials and Methods 125
9.2.1 Materials 125
9.2.2 Enzymatic Acylation Procedure 125
9.2.3 Analytical Methods 125
9.2.4 Purification and Chemical Structure Determination of Esters 125
9.3 Results and Discussion 125
9.3.1 Modification of Natural Antioxidants in Organic Solvents 126
9.3.1.1 Enzymatic Acylation of Rutin and Silybin with Dicarboxylic
Acids 126
9.3.1.2 Effect of Organic Solvent 127
9.3.1.3 Effect of Substrate Concentration 127
9.3.2 Modification of Natural Antioxidants in Ionic Liquid Media 128
9.3.2.1 Enzymatic Acylation of Natural Polyhydroxylated Compounds 128
9.3.2.2 Effect of Substrate Concentration 130
9.3.2.3 Effect of Acyl Donor Nature: Synthesis of Hybrid Antioxidants 130
9.4 Conclusions 131
References 132
10 Biocatalysis Applied to the Synthesis of Nucleoside Analogs 135
Vicente Color
10.1 Introduction 135
10.2 Chemoenzymatic Modification of the Sugar 136
10.3 Resolution and Anomeric Separation 143
10.4 Biotransformations that Modify the Base 145
10.5 Transglycosylation for the Synthesis of Nucleosides 147
10.6 Summary 149
References 150
11 Efficient Fructooligosaccharide Synthesis with a Fructosyltransferase
from Aspergillus aculeatus 153
Francisco J. Plou, Miguel Alcalde, Iraj Ghazi, Lucia Ferndndez-Arrojo and
Antonio Ballesteros
11.1 Introduction 153
11.2 Purification of Fructosyltransferase in Pectmex Ultra SP-L 155
11.3 Properties of Fructosyltransferase from A. aculeatus 157 ,
i
Contents IX
11.3.1 Substrate Specificity 157
11.3.2 Effect of pH and Temperature 158
11.3.3 Influence of Chemicals 158
11.3.4 Kinetic Behavior 159
11.3.5 Fructooligosaccharide Production 159
11.4 Immobilization of Fructosyltransferase from A. aculeatus 161
11.4.1 Sepabeads EC-EP as Immobilization Carriers 161
11.4.2 Effect of pH and Ionic Strength on Immobilization 162
11.4.3 Application of Immobilized Biocatalysts to Fructooligosaccharide
Synthesis 164
11.5 Fructooligosaccharide Production Using Sugar Beet Syrup and
Molasses 164
11.5.1 Sugar Beet Syrup and Molasses as Low-cost Feedstock for
Fructooligosaccharide Synthesis 164
11.5.2 Batch Production of Fructooligosaccharide 167
11.6 Conclusions 168
Acknowledgments 168
References 168
12 Hydantoin Racemase: the Key Enzyme for the Production of Optically
Pure a-Amino Acids 173
Francisco Javier Las Heras-Vdzquez, Josefa Maria Clemente-Jime'nez,
Sergio Martinez-Rodriguez and Felipe Rodriguez-Vico
12.1 Introduction 173
12.2 Search for New Hydantoin Racemases and Molecular
Characterization 175
12.3 Biochemical Characterization of Hydantoin Racemase Enzymes 180
12.4 Substrate Enantioselectivity and Kinetic Analysis of Hydantoin
Racemases 181
12.5 Proposal for a Reaction Mechanism of Hydantoin Racemase
Enzymes 183
12.6 Design of a Tailormade Recombinant Biocatalyst Including Hydantoin
Racemase Enzymes for Optically Pure D-Amino Acid Production 187
Acknowledgments 192
References 192
13 Chemo-enzymatic Deracemization Methods 195
Davide Tessaro, Cianluca Molla, Loredano Pollegioni and Stefano Servi
13.1 Introduction 195
13.2 Deracemization Methods for a- and fi-Hydroxy Acids 196
13.2.1 Deracemization of Hydroxy Acids by DKR (Hydrolytic Enzymes +
Ruthenium-based Racemization Catalysts) 197
13.2.2 Deracemization of Hydroxy Acids by DKR with a Two-enzyme
System 198
13.2.3 Deracemization of Hydroxy Acids by Stereoinversion 199
X Contents
13.2.4 Deracemization of Hydroxy Acids by Microbial Stereoinversion 200
13.3 Deracemization of a-Hydroxy Nitriles 201
13.4 Deracemization of a-Amino Acids 202
13.4.1 Deracemization of a-Amino Acids by Stereoinversion 202
13.4.1.1 Deracemization by Stereoinversion via the Two-enzyme System
D-Amino Acid Oxidase and L-Amino Transferase 202
13.4.1.2 Deracemization by Stereoinversion via the Two-enzyme System
D-Amino Acid Oxidase and L-Leucme Dehydrogenase 204
13.4.1.3 Deracemization by Stereoinversion via the Three-enzyme System
L-Amino Acid Oxidase, D-Amino Transferase and Amino Acid
Racemase 204
13.4.2 Deracemization of a-Amino Acids via DKR 205
13.4.2.1 Deracemization of a-Amino Acids via Enzyme-catalyzed DKR
Coupled with In Situ Racemization 205
13.5 Useful Enzymes for Deracemization Methods 213
13.5.1 Amino Acid Oxidases 213
13.5.1.1 D-Amino Acid Oxidase (EC 1.4.3.3) 213
13.5.1.2 L-Amino Acid Oxidase (EC 1.4.3.2) 216
13.5.2 Amino Acid Racemases 217
13.5.2.1 PLP-dependent Racemases 217
13.5.2.2 PLP-independent Racemases 220
13.5.2.3 Mandelate Racemase (EC 5.1.2.2) 221
13.5.3 Transaminases 221
13.5.3.1 L-Amino Transferases (EC 2.6.1.x) 222
13.5.3.2 D-Amino Transferases (EC 2.6.1.21) 223
13.6 Summary and Outlook 223
References 223
14 Nitrilases from Filamentous Fungi 229
Ludmila Martinkovd, Vojtech Vejvoda, Ondrej Kaplan, Vladimir Kren,
Karel Bezouika and Maria Cantarella
14.1 Introduction 229
14.2 Distribution and Evolutionary Relationship of Fungal Nitrilases 230
14.2.1 Molecular Genetic Analysis 230
14.2.2 Selection and Screening of Nitrilase Activity 232
14.3 Structural Properties 234
14.4 Catalytic Properties 236
14.4.1 Reaction Mechanism 236
14.4.2 Substrate Specificity 238
14.4.3 Activity and Stability 240
14.5 Conclusions and Outlook 242
Acknowledgment 243
References 243
I
Contents I XI
15 Nitrilase- and Nitrile Hydratase-catalyzed Enantioselective Preparation
of Non-proteinogenic Amino Acids 247
Norbert Klempier and Margit Winkler
15.1 Introduction 247
15.2 Nitrile Hydratase/Amidase Biotransformations 249
15.2.1 Protecting Groups for Amino Nitriles 249
15.2.2 Enantioselective Hydrolysis of |3-Amino Nitriles 250
15.3 Nitrilase Biotransformations 253
15.3.1 Enantioselective Hydrolysis of (5-Amino Nitriles 253
15.3.2 Enantioselective Hydrolysis of "y-Amino Nitriles 255
15.3.3 Nitrile Hydratase Activity of Nitrilases 257
References 258
16 Nitrilases in the Enantioselective Synthesis of a-Hydroxycarboxylic
Acids 261
Fred van Rantwijk, Cesar Mateo, Andrzej Chmura, Bruno C. M. Fernandes
and Roger A Sheldon
16.1 Routes to Enantiomerically Pure a-Hydroxycarboxylic Acids 261
16.2 Nitrilase-mediated Hydrolysis of Cyanohydrins 262
16.3 A Bienzymatic Approach to Enantiopure 2-Hydroxycarboxylic
Acids 264
16.4 Stabilization of NLases as Cross-linked Enzyme Aggregates 265
16.5 Hydrocyanation and Hydrolysis in a Bienzymatic Cascade 265
16.6 Nitrilases Acting as Nitrile Hydratases 267
16.7 Conclusion 270
Acknowledgments 271
References 271
17 UF-Membrane Bioreactors for Kinetics Characterization of Nitrile
Hydratase-Amidase-catalyzed Reactions: a Short Survey 273
Maria Cantarella, Alberto Callifuoco, Agata Spera, Laura Cantarella, Ondfej
Kaplan and Ludmila Martinkovd
17.1 Introduction 273
17.2 Experiment Design 275
17.3 Temperature Dependence of the Nitrile Hydratase-Amidase Cascade
System 275
17.4 CSMR Investigations 277
17.5 Substrate Concentration Effects on the Reaction Rate, Enzyme
Stability, Substrate Conversion, and Reactor Capacity 279
17.6 Concluding Remarks 283
Acknowledgments 285
References 285
XII Contents
18 Enzymes Catalyzing C—C Bond Formation for the Synthesis of
Monosaccharide Analogs 287
Laurence Hecquet, Virgil Hilaine, Franck Charmantray and Marielle
Lemaire
18.1 Introduction 287
18.2 Recent Syntheses Involving Transketolase and Fructose-1,6-
iusphosphate Aldolase 287
18.2.1 DHAP Syntheses 288
18.2.1.1 DHAP Synthesis from Dihydroxyacetone 289
18.2.1.2 DHAP Synthesis from Rac-Glycidol 290
18.2.2 Synthesis of Aminocyclitols 291
18.2.3 Synthesis of 5-D-Xylulose and 5-D-Xylose Analogs 293
18.2.3.1 Synthesis of 5-halo-D-xylulose 293
18.2.3.2 Synthesis of 5-thio-D-xylopyranose 21 293
18.3 Modification of Substrate Specificity of Yeast Transketolase 295
18.4 Conclusion 296
References 297
19 Novel Strategies in Aldolase-catalyzed Synthesis of Iminosugars 299
Pere Clapis, Georg A Sprenger and Jesus Joglar
19.1 Introduction 299
19.2 DHAP-Aldolase-mediated Synthesis of Iminosugars from N-Cbz-
amino Aldehydes 301
19.2.1 Reaction Media 301
19.2.2 Aldolase-catalyzed Aldol Additions of DHAP to N-Cbz-Amino
Aldehydes 301
19.2.3 Effect of N-Protecting Groups 304
19.2.4 Synthesis of Iminosugars: Reductive Amination 306
19.3 D-Fructose-6-Phosphate Aldolase as Catalyst for Iminosugar
Synthesis 307
19.4 Summary and Outlook 309
References 309
20 Biocatalytic Asymmetric Oxidations with Oxygen 313
Roland Wohlgemuth
20.1 Introduction 313
20.2 Biocatalytic Asymmetric Oxidations with Oxidases 317
20.3 Biocatalytic Asymmetric Oxidations with Peroxidases 319
20.4 Biocatalytic Asymmetric Oxidations with Dehydrogenases 320
20.5 Biocatalytic Asymmetric Oxidations with Monooxygenases 321
20.6 Biocatalytic Asymmetric Oxidations with Dioxygenases 325
20.7 Biocatalytic Asymmetric Oxidations with Other Enzymes 328
20.8 Outlook 331
Acknowledgments 331
References 332
1
Contents XIII
21 Second Generation Baeyer-Villiger Biocatalysts 339
Veronique Alphand, Marco W. Fraaije, Marko D. Mihovilovic and Gianluca
(Molina
21.1 Introduction 339
21.2 BVMO Enzyme Platform 341
21.3 Engineering of BVMOs 342
21.4 Baeyer-Villiger Biooxidation in Synthetic Chemistry 347
21.4.1 Chemoselectivity 347
21.4.2 Dynamic Kinetic Resolutions 350
21.4.3 Regio- and Stereoselectivity 351
21.4.4 Natural Product and Bioactive Compound Synthesis 354
21.5 BVMOs in Stereoselective Sulfoxidations 357
21.6 Towards a Technology Platform 358
21.6.1 Fermentation Up-Scaling 358
21.6.1.1 Whole Cells 358
21.6.1.2 Enzyme 361
21.6.2 Immobilization of BVMOs 361
21.6.3 Self-sufficient Fusion Protein BVMOs 361
21.7 Outlook 363
References 363
Index 369 |
| any_adam_object | 1 |
| author2 | Fessner, Wolf-Dieter 1955- |
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| callnumber-sort | TP 3248.65 E59 |
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| discipline | Chemie / Pharmazie Biologie Chemie Chemie-Ingenieurwesen Biotechnologie |
| format | Book |
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| genre_facet | Aufsatzsammlung |
| id | DE-604.BV035265490 |
| illustrated | Illustrated |
| indexdate | 2024-07-20T10:00:56Z |
| institution | BVB |
| isbn | 9783527320714 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-017070952 |
| oclc_num | 299239569 |
| open_access_boolean | |
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| physical | XXIII, 375 S. Ill., graph. Darst. |
| publishDate | 2009 |
| publishDateSearch | 2009 |
| publishDateSort | 2009 |
| publisher | WILEY-VCH |
| record_format | marc |
| spelling | Modern biocatalysis stereoselective and environmentally friendly reactions ed. by Wolf-Dieter Fessner ... Weinheim WILEY-VCH 2009 XXIII, 375 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Biocatalysis Biotechnology methods Catalysis Enzymes Biotechnology Enzymes physiology Biokatalyse (DE-588)4393622-2 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Biokatalyse (DE-588)4393622-2 s DE-604 Fessner, Wolf-Dieter 1955- (DE-588)121666662 edt text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3112955&prov=M&dok_var=1&dok_ext=htm Inhaltstext HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017070952&sequence=000004&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Modern biocatalysis stereoselective and environmentally friendly reactions Biocatalysis Biotechnology methods Catalysis Enzymes Biotechnology Enzymes physiology Biokatalyse (DE-588)4393622-2 gnd |
| subject_GND | (DE-588)4393622-2 (DE-588)4143413-4 |
| title | Modern biocatalysis stereoselective and environmentally friendly reactions |
| title_auth | Modern biocatalysis stereoselective and environmentally friendly reactions |
| title_exact_search | Modern biocatalysis stereoselective and environmentally friendly reactions |
| title_full | Modern biocatalysis stereoselective and environmentally friendly reactions ed. by Wolf-Dieter Fessner ... |
| title_fullStr | Modern biocatalysis stereoselective and environmentally friendly reactions ed. by Wolf-Dieter Fessner ... |
| title_full_unstemmed | Modern biocatalysis stereoselective and environmentally friendly reactions ed. by Wolf-Dieter Fessner ... |
| title_short | Modern biocatalysis |
| title_sort | modern biocatalysis stereoselective and environmentally friendly reactions |
| title_sub | stereoselective and environmentally friendly reactions |
| topic | Biocatalysis Biotechnology methods Catalysis Enzymes Biotechnology Enzymes physiology Biokatalyse (DE-588)4393622-2 gnd |
| topic_facet | Biocatalysis Biotechnology methods Catalysis Enzymes Biotechnology Enzymes physiology Biokatalyse Aufsatzsammlung |
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