Multi-step enzyme catalysis: biotransformations and chemoenzymatic synthesis
Gespeichert in:
| Format: | Buch |
|---|---|
| Sprache: | English |
| Veröffentlicht: |
Weinheim
WILEY-VCH
2008
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| Ausgabe: | 1. Aufl. |
| Schlagworte: | |
| Online-Zugang: | Inhaltstext Inhaltsverzeichnis |
| Beschreibung: | XV, 241 S. Ill., graph. Darst. 240 mm x 170 mm |
| ISBN: | 9783527319213 3527319212 |
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| 245 | 1 | 0 | |a Multi-step enzyme catalysis |b biotransformations and chemoenzymatic synthesis |c ed. by. Eduardo Garcia-Junceda |
| 250 | |a 1. Aufl. | ||
| 264 | 1 | |a Weinheim |b WILEY-VCH |c 2008 | |
| 300 | |a XV, 241 S. |b Ill., graph. Darst. |c 240 mm x 170 mm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 4 | |a Catalysis | |
| 650 | 4 | |a Enzymes |x Biotechnology | |
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Datensatz im Suchindex
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| adam_text |
V
Contents
Preface XI
List of Contributors XIII
1 Asymmetric Transformations by Coupled Enzyme and Metal Catalysis:
Dynamic Kinetic Resolution 1
Mahn-Joo Kim, Jaiwook Park, and Yoon Kyung Choi
1.1 Introduction 1
1.2 Some Fundamentals for DKR 2
1.2.1 Enzymes for Kinetic Resolution 2
1.2.2 Metal Catalysts for Racemization 3
1.2.3 Enzyme-Metal Combination for DKR 5
1.2.4 (R)- and (S)-Selective DKR 5
1.3 Examples of DKR 6
1.3.1 First DKR of Secondary Alcohols 6
1.3.2 DKR of Secondary Alcohols with Racemization Catalyst 1 6
1.3.3 DKR of Secondary Alcohols with Racemization Catalyst 2 8
1.3.4 DKR of Secondary Alcohols with Racemization Catalyst 3 9
1.3.5 DKR of Secondary Alcohols with Racemization Catalyst 4 10
1.3.6 DKR of Secondary Alcohols with Racemization Catalyst 5 10
1.3.7 DKR of Secondary Alcohols with Racemization Catalyst 6 11
1.3.8 DKR of Secondary Alcohols with Racemization Catalyst 7 12
1.3.9 DKR of Secondary Alcohols with Air-Stable Racemization Catalysts 13
1.3.10 DKR of Secondary Alcohols with Racemization Catalyst 10 14
1.3.11 DKR of Secondary Alcohols with Aluminum Catalysts 14
1.3.12 DKR of Secondary Alcohols with Vanadium Catalysts 15
1.4 Conclusions 16
References 17
Multi-Step Enzyme Catalysis: Biotransformations and Chemoenzymatic Synthesis
Edited by Eduardo Garcia-Junceda
Copyright © 2008 WILEY-VCH Verlag GmbH Co. KGaA, Weinheim
ISBN: 978-3-527-31921-3
VII Contents
2 Chemoenzymatic Routes to Enantiomerically Pure Amino Acids
and Amines 21
Nicholas]. Turner
2.1 Introduction 21
2.2 Amino Acids 23
2.3 Amines 33
References 38
3 Oxidizing Enzymes in Multi-Step Biotransformation Processes 41
Stephanie C. Burton and Marilize le Roes-Hill
3.1 Oxidizing Enzymes in Biocatalysis 41
3.2 Classes of Oxidizing Enzymes 41
3.3 Mechanisms of Biological Oxidation and Implications for Multi-Enzyme
Biocatalysis 44
3.4 Multi-Step Biotransformation Processes Involving Oxidation 45
3.5 Design and Development of New Multi-Enzyme Oxidizing Processes 48
3.5.1 Coupling Redox Enzymes 48
3.5.2 Cofactor Recycle in Multi-Step Oxidizing Biocatalytic Systems 51
3.6 Examples of Multi-Enzyme Biotransformation Processes Involving
Oxidizing Enzymes 52
3.6.1 Coupling of Oxidases with Non-Redox Enzymes 53
3.6.2 Biocatalytic Systems Involving Coupled Oxidizing Enzymes 53
3.7 Multi-Enzyme Systems in Whole-Cell Biotransformations and Expression
of Redox Systems in Recombinant Hosts 55
3.8 Other Applications of Multi-Enzyme Oxidizing Systems 56
3.9 Conclusions 58
References 58
4 Dihydroxyacetone Phosphate-Dependent Aldolases in the Core
of Multi-Step Processes 61
Laura Iturrate and Eduardo Carcia-Junceda
4.1 Introduction 61
4.2 DHAP-Dependent Aldolases 63
4.2.1 Problem of DHAP Dependence 63
4.2.2 DHAP-Dependent Aldolases in the Core of Aza Sugar Synthesis 68
4.2.3 Combined Use of Aldolases and Isomerases for the Synthesis of
Natural and Unnatural Sugars 71
4.2.4 DHAP-Dependent Aldolases in the Synthesis of Natural Products 73
4.3 Fructose-6-Phosphate Aldolase: An Alternative to DHAP-Dependent
Aldolases? 76
4.4 Conclusions 78
References 79
Contents I VII
5 Multi-Enzyme Systems for the Synthesis of Clycoconjugates 83
Birgit Sauerzapfe and Lothar Elling
5.1 Introduction 83
5.2 In Vitro and In Vivo Multi-Enzyme Systems 85
5.3 Combinatorial Biocatalysis 86
5.3.1 Synthesis and In Situ Regeneration of Nucleotide Sugars 88
5.3.2 Synthesis of Oligosaccharides, Glycopeptides and Glycolipids
Oligosaccharides 94
5.4 Combinatorial Biosynthesis 97
5.4.1 Synthesis of Oligosaccharides with Metabolically Engineered Cells 98
5.5 Conclusions 102
References 102
6 Enzyme-Catalyzed Cascade Reactions 109
Roger A. Sheldon
6.1 Introduction 109
6.2 Enzyme Immobilization 110
6.3 Reaction Types: General Considerations 111
6.4 Chiral Alcohols 112
6.5 Chiral Amines 114
6.6 Chiral Carboxylic Acid Derivatives 121
6.7 C-C Bond Formation: Aldolases 127
6.8 Oxidations with O2 and H2O2 130
6.9 Conclusions and Prospects 131
References 132
7 Multi-modular Synthases as Tools of the Synthetic Chemist 137
Michael D. Burkart andjunhua Tao
7.1 Introduction 137
7.2 Excised Domains for Chemical Transformations 139
7.2.1 Function of Individual Domains and Domain Autonomy 139
7.2.2 Heterocyclization and Aromatization 139
7.2.3 Macrocyclization 144
7.2.4 Halogenation 147
7.2.5 Glycosylation 150
7.2.6 Methyltransferases 151
7.2.7 Oxidation 153
7.3 Conclusions 155
References 156
VIIII Contents
8 Modifying the Clycosylation Pattern in Actinomycetes by
Combinatorial Biosynthesis 359
Jose A. Salas and Carmen Mindez
8.1 Bioactive Natural Products in Actinomycetes 359
8.2 Deoxy Sugar Biosynthesis and Gene Clusters 363
8.3 Characterization of Sugar Biosynthesis Enzymes 161
8.4 Strategies for the Generation of Novel Glycosylated Derivatives 165
8.4.1 Gene Inactivation 165
8.4.2 Gene Expression 366
8.4.3 Combining Gene Inactivation and Gene Expression 166
8.4.4 Endowing a Host with the Capability of Synthesizing Different
Sugars 366
8.5 Generation of Glycosylated Derivatives of Bioactive Compounds 166
8.5.1 Macrolides 167
8.5.2 Aureolic Acid Group 175
8.5.3 Angucyclines 181
8.5.4 Anthracyclines 186
8.5.5 Indolocarbazoles 191
8.5.6 Aminocoumarins 193
References 3 94
9 Microbial Production of DNA Building Blocks 399
Jun Ogawa, Nobuyuki Horinouchi, and Sakayu Shimizu
9.1 Introduction 199
9.2 Screening of Acetaldehyde-Tolerant Deoxyriboaldolase and Its
Application for DR5P Synthesis 200
9.3 Construction of Deoxyriboaldolase-Overexpressing E. coli and Metabolic
Analysis of the E. coli Transformants for DR5P Production from
Glucose and Acetaldehyde 201
9.4 Efficient Production of DR5P from Glucose and Acetaldehyde by
Coupling of the Alcoholic Fermentation System of Baker's Yeast and
Deoxyriboaldolase-Expressing E. coli 203
9.5 Biochemical Retrosynthesis of 2'-Deoxyribonucleosides from Glucose
Acetaldehyde and a Nucleobase: Three-Step Multi-Enzyme-Catalyzed
Synthesis 204
9.6 One-Pot Multi-Step Enzymatic Synthesis of 2'-Deoxyribonucleoside from
Glucose, Acetaldehyde and a Nucleobase 206
9.7 Improvement of the One-Pot Multi-Step Enzymatic Process for Practical
Production of 2'-Deoxyribonucleoside from Glucose, Acetaldehyde
and a Nucleobase 207
9.8 Conclusions 208
References 210
!
!
Contents IIX
10 Combination of Biocatalysis and Chemical Catalysis for the Preparation
of Pharmaceuticals Through Multi-Step Syntheses 213
Vicente Gotor-Femdndez, Rosario Brieva, and Vicente Cotor
10.1 Introduction: Biocatalysis and Chemical Catalysis 213
10.2 Pharmaceuticals with Hydrolases 214
10.2.1 Enzymatic Hydrolysis 214
10.2.2 Enzymatic Transesterification 219
10.2.3 Enzymatic Aminolysis 222
10.3 Pharmaceuticals with Oxidoreductases 226
10.4 Pharmaceuticals with Lyases 227
10.5 Conclusions 230
References 231
Index 235 |
| adam_txt |
V
Contents
Preface XI
List of Contributors XIII
1 Asymmetric Transformations by Coupled Enzyme and Metal Catalysis:
Dynamic Kinetic Resolution 1
Mahn-Joo Kim, Jaiwook Park, and Yoon Kyung Choi
1.1 Introduction 1
1.2 Some Fundamentals for DKR 2
1.2.1 Enzymes for Kinetic Resolution 2
1.2.2 Metal Catalysts for Racemization 3
1.2.3 Enzyme-Metal Combination for DKR 5
1.2.4 (R)- and (S)-Selective DKR 5
1.3 Examples of DKR 6
1.3.1 First DKR of Secondary Alcohols 6
1.3.2 DKR of Secondary Alcohols with Racemization Catalyst 1 6
1.3.3 DKR of Secondary Alcohols with Racemization Catalyst 2 8
1.3.4 DKR of Secondary Alcohols with Racemization Catalyst 3 9
1.3.5 DKR of Secondary Alcohols with Racemization Catalyst 4 10
1.3.6 DKR of Secondary Alcohols with Racemization Catalyst 5 10
1.3.7 DKR of Secondary Alcohols with Racemization Catalyst 6 11
1.3.8 DKR of Secondary Alcohols with Racemization Catalyst 7 12
1.3.9 DKR of Secondary Alcohols with Air-Stable Racemization Catalysts 13
1.3.10 DKR of Secondary Alcohols with Racemization Catalyst 10 14
1.3.11 DKR of Secondary Alcohols with Aluminum Catalysts 14
1.3.12 DKR of Secondary Alcohols with Vanadium Catalysts 15
1.4 Conclusions 16
References 17
Multi-Step Enzyme Catalysis: Biotransformations and Chemoenzymatic Synthesis
Edited by Eduardo Garcia-Junceda
Copyright © 2008 WILEY-VCH Verlag GmbH Co. KGaA, Weinheim
ISBN: 978-3-527-31921-3
VII Contents
2 Chemoenzymatic Routes to Enantiomerically Pure Amino Acids
and Amines 21
Nicholas]. Turner
2.1 Introduction 21
2.2 Amino Acids 23
2.3 Amines 33
References 38
3 Oxidizing Enzymes in Multi-Step Biotransformation Processes 41
Stephanie C. Burton and Marilize le Roes-Hill
3.1 Oxidizing Enzymes in Biocatalysis 41
3.2 Classes of Oxidizing Enzymes 41
3.3 Mechanisms of Biological Oxidation and Implications for Multi-Enzyme
Biocatalysis 44
3.4 Multi-Step Biotransformation Processes Involving Oxidation 45
3.5 Design and Development of New Multi-Enzyme Oxidizing Processes 48
3.5.1 Coupling Redox Enzymes 48
3.5.2 Cofactor Recycle in Multi-Step Oxidizing Biocatalytic Systems 51
3.6 Examples of Multi-Enzyme Biotransformation Processes Involving
Oxidizing Enzymes 52
3.6.1 Coupling of Oxidases with Non-Redox Enzymes 53
3.6.2 Biocatalytic Systems Involving Coupled Oxidizing Enzymes 53
3.7 Multi-Enzyme Systems in Whole-Cell Biotransformations and Expression
of Redox Systems in Recombinant Hosts 55
3.8 Other Applications of Multi-Enzyme Oxidizing Systems 56
3.9 Conclusions 58
References 58
4 Dihydroxyacetone Phosphate-Dependent Aldolases in the Core
of Multi-Step Processes 61
Laura Iturrate and Eduardo Carcia-Junceda
4.1 Introduction 61
4.2 DHAP-Dependent Aldolases 63
4.2.1 Problem of DHAP Dependence 63
4.2.2 DHAP-Dependent Aldolases in the Core of Aza Sugar Synthesis 68
4.2.3 Combined Use of Aldolases and Isomerases for the Synthesis of
Natural and Unnatural Sugars 71
4.2.4 DHAP-Dependent Aldolases in the Synthesis of Natural Products 73
4.3 Fructose-6-Phosphate Aldolase: An Alternative to DHAP-Dependent
Aldolases? 76
4.4 Conclusions 78
References 79
Contents I VII
5 Multi-Enzyme Systems for the Synthesis of Clycoconjugates 83
Birgit Sauerzapfe and Lothar Elling
5.1 Introduction 83
5.2 In Vitro and In Vivo Multi-Enzyme Systems 85
5.3 Combinatorial Biocatalysis 86
5.3.1 Synthesis and In Situ Regeneration of Nucleotide Sugars 88
5.3.2 Synthesis of Oligosaccharides, Glycopeptides and Glycolipids
Oligosaccharides 94
5.4 Combinatorial Biosynthesis 97
5.4.1 Synthesis of Oligosaccharides with Metabolically Engineered Cells 98
5.5 Conclusions 102
References 102
6 Enzyme-Catalyzed Cascade Reactions 109
Roger A. Sheldon
6.1 Introduction 109
6.2 Enzyme Immobilization 110
6.3 Reaction Types: General Considerations 111
6.4 Chiral Alcohols 112
6.5 Chiral Amines 114
6.6 Chiral Carboxylic Acid Derivatives 121
6.7 C-C Bond Formation: Aldolases 127
6.8 Oxidations with O2 and H2O2 130
6.9 Conclusions and Prospects 131
References 132
7 Multi-modular Synthases as Tools of the Synthetic Chemist 137
Michael D. Burkart andjunhua Tao
7.1 Introduction 137
7.2 Excised Domains for Chemical Transformations 139
7.2.1 Function of Individual Domains and Domain Autonomy 139
7.2.2 Heterocyclization and Aromatization 139
7.2.3 Macrocyclization 144
7.2.4 Halogenation 147
7.2.5 Glycosylation 150
7.2.6 Methyltransferases 151
7.2.7 Oxidation 153
7.3 Conclusions 155
References 156
VIIII Contents
8 Modifying the Clycosylation Pattern in Actinomycetes by
Combinatorial Biosynthesis 359
Jose A. Salas and Carmen Mindez
8.1 Bioactive Natural Products in Actinomycetes 359
8.2 Deoxy Sugar Biosynthesis and Gene Clusters 363
8.3 Characterization of Sugar Biosynthesis Enzymes 161
8.4 Strategies for the Generation of Novel Glycosylated Derivatives 165
8.4.1 Gene Inactivation 165
8.4.2 Gene Expression 366
8.4.3 Combining Gene Inactivation and Gene Expression 166
8.4.4 Endowing a Host with the Capability of Synthesizing Different
Sugars 366
8.5 Generation of Glycosylated Derivatives of Bioactive Compounds 166
8.5.1 Macrolides 167
8.5.2 Aureolic Acid Group 175
8.5.3 Angucyclines 181
8.5.4 Anthracyclines 186
8.5.5 Indolocarbazoles 191
8.5.6 Aminocoumarins 193
References 3 94
9 Microbial Production of DNA Building Blocks 399
Jun Ogawa, Nobuyuki Horinouchi, and Sakayu Shimizu
9.1 Introduction 199
9.2 Screening of Acetaldehyde-Tolerant Deoxyriboaldolase and Its
Application for DR5P Synthesis 200
9.3 Construction of Deoxyriboaldolase-Overexpressing E. coli and Metabolic
Analysis of the E. coli Transformants for DR5P Production from
Glucose and Acetaldehyde 201
9.4 Efficient Production of DR5P from Glucose and Acetaldehyde by
Coupling of the Alcoholic Fermentation System of Baker's Yeast and
Deoxyriboaldolase-Expressing E. coli 203
9.5 Biochemical Retrosynthesis of 2'-Deoxyribonucleosides from Glucose
Acetaldehyde and a Nucleobase: Three-Step Multi-Enzyme-Catalyzed
Synthesis 204
9.6 One-Pot Multi-Step Enzymatic Synthesis of 2'-Deoxyribonucleoside from
Glucose, Acetaldehyde and a Nucleobase 206
9.7 Improvement of the One-Pot Multi-Step Enzymatic Process for Practical
Production of 2'-Deoxyribonucleoside from Glucose, Acetaldehyde
and a Nucleobase 207
9.8 Conclusions 208
References 210
!
!
Contents IIX
10 Combination of Biocatalysis and Chemical Catalysis for the Preparation
of Pharmaceuticals Through Multi-Step Syntheses 213
Vicente Gotor-Femdndez, Rosario Brieva, and Vicente Cotor
10.1 Introduction: Biocatalysis and Chemical Catalysis 213
10.2 Pharmaceuticals with Hydrolases 214
10.2.1 Enzymatic Hydrolysis 214
10.2.2 Enzymatic Transesterification 219
10.2.3 Enzymatic Aminolysis 222
10.3 Pharmaceuticals with Oxidoreductases 226
10.4 Pharmaceuticals with Lyases 227
10.5 Conclusions 230
References 231
Index 235 |
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| id | DE-604.BV035107947 |
| illustrated | Illustrated |
| index_date | 2024-07-02T22:16:30Z |
| indexdate | 2024-07-20T09:52:48Z |
| institution | BVB |
| isbn | 9783527319213 3527319212 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-016775828 |
| oclc_num | 230183618 |
| open_access_boolean | |
| owner | DE-703 DE-19 DE-BY-UBM DE-1028 DE-92 DE-83 DE-11 DE-M49 DE-BY-TUM |
| owner_facet | DE-703 DE-19 DE-BY-UBM DE-1028 DE-92 DE-83 DE-11 DE-M49 DE-BY-TUM |
| physical | XV, 241 S. Ill., graph. Darst. 240 mm x 170 mm |
| publishDate | 2008 |
| publishDateSearch | 2008 |
| publishDateSort | 2008 |
| publisher | WILEY-VCH |
| record_format | marc |
| spelling | Multi-step enzyme catalysis biotransformations and chemoenzymatic synthesis ed. by. Eduardo Garcia-Junceda 1. Aufl. Weinheim WILEY-VCH 2008 XV, 241 S. Ill., graph. Darst. 240 mm x 170 mm txt rdacontent n rdamedia nc rdacarrier Catalysis Enzymes Biotechnology Enzymkatalyse (DE-588)4152480-9 gnd rswk-swf Enzymkatalyse (DE-588)4152480-9 s DE-604 Garcia-Junceda, Eduardo Sonstige (DE-588)136279902 oth text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3089704&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=016775828&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Multi-step enzyme catalysis biotransformations and chemoenzymatic synthesis Catalysis Enzymes Biotechnology Enzymkatalyse (DE-588)4152480-9 gnd |
| subject_GND | (DE-588)4152480-9 |
| title | Multi-step enzyme catalysis biotransformations and chemoenzymatic synthesis |
| title_auth | Multi-step enzyme catalysis biotransformations and chemoenzymatic synthesis |
| title_exact_search | Multi-step enzyme catalysis biotransformations and chemoenzymatic synthesis |
| title_exact_search_txtP | Multi-step enzyme catalysis biotransformations and chemoenzymatic synthesis |
| title_full | Multi-step enzyme catalysis biotransformations and chemoenzymatic synthesis ed. by. Eduardo Garcia-Junceda |
| title_fullStr | Multi-step enzyme catalysis biotransformations and chemoenzymatic synthesis ed. by. Eduardo Garcia-Junceda |
| title_full_unstemmed | Multi-step enzyme catalysis biotransformations and chemoenzymatic synthesis ed. by. Eduardo Garcia-Junceda |
| title_short | Multi-step enzyme catalysis |
| title_sort | multi step enzyme catalysis biotransformations and chemoenzymatic synthesis |
| title_sub | biotransformations and chemoenzymatic synthesis |
| topic | Catalysis Enzymes Biotechnology Enzymkatalyse (DE-588)4152480-9 gnd |
| topic_facet | Catalysis Enzymes Biotechnology Enzymkatalyse |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=3089704&prov=M&dok_var=1&dok_ext=htm http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016775828&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT garciajuncedaeduardo multistepenzymecatalysisbiotransformationsandchemoenzymaticsynthesis |