Multi-step enzyme catalysis : biotransformations and chemoenzymatic synthesis

Title:

Publication Information:

Weinheim, GW : Wiley-VCH, 2008

Physical Description:

xv, 241 p. : ill. ; 25 cm.

ISBN:

9783527319213

Subject Term:

Catalysis

Enzymes -- Biotechnology

Added Author:

Garcia-Junceda, Eduardo

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Library	Item Barcode	Call Number	Material Type	Item Category 1	Status
Searching... PSZ JB	30000010201824	QD505 M844 2008	Open Access Book	Book	Searching... Unknown

The first comprehensive coverage of this unique and interdisciplinary field provides a complete overview, covering such topics as chemoenzymatic synthesis, microbial production of DNA building blocks, asymmetric transformations by coupled enzymes and much more. By combining enzymatic and synthetic organic steps, the use of multi-enzyme complexes and other techniques opens the door to reactions hitherto unknown, making this monograph of great interest to biochemists, organic chemists, and chemists working with/on organometallics, as well as catalytic chemists, biotechnologists, and those working in the pharmaceutical and fine chemical industries.

Author Notes

Eduardo Garcia-Junceda received his PhD at the Plant Physiology Department at the University of Madrid. He joined Chi-Huey Wong's Group at The Scripps Research Institute (La Jolla, California) as postdoctoral fellow. After his return to Spain in 1995, he was appointed Research Staff Member in the Institute of Organic Chemistry of CSIC in 1997. His research interests concentrate on molecular biology applied to organic synthesis and enzyme catalysis.

Mahn-Joo Kim and Jaiwook Park and Yoon Kyung ChoiNicholas J. TurnerStephanie G. Burton and Marilize le Roes-HillLaura Iturrate and Eduardo Garcia-JuncedaBirgit Sauerzapfe and Lothar EllingRoger A. SheldonMichael D. Burkart and Junhua TaoJose A. Salas and Carmen MendezJun Ogawa and Nobuyuki Horinouchi and Sakayu ShimizuVicente Gotor and Rosario Brieva and Vicente Gotor

Preface	p. XI
Lise of Contributors	p. XIII
1 Asymmetric Transformations by Coupled Enzyme and Metal Catalysis: Dynamic Kinetic Resolution	p. 1
1.1 Introduction	p. 1
1.2 Some Fundamentals for DKR	p. 2
1.2.1 Enzymes for Kinetic Resolution	p. 2
1.2.2 Metal Catalysts for Racemization	p. 3
1.2.3 Enzyme-Metal Combination for DKR	p. 5
1.2.4 (R)- and (S)-Selective DKR	p. 5
1.3 Examples of DKR	p. 6
1.3.1 First DKR of Secondary Alcohols	p. 6
1.3.2 DKR of Secondary Alcohols with Racemization Catalyst 1	p. 6
1.3.3 DKR of Secondary Alcohols with Racemization Catalyst 2	p. 8
1.3.4 DKR of Secondary Alcohols with Racemization Catalyst 3	p. 9
1.3.5 DKR of Secondary Alcohols with Racemization Catalyst 4	p. 10
1.3.6 DKR of Secondary Alcohols with Racemization Catalyst 5	p. 10
1.3.7 DKR of Secondary Alcohols with Racemization Catalyst 6	p. 11
1.3.8 DKR of Secondary Alcohols with Racemization Catalyst 7	p. 12
1.3.9 DKR of Secondary Alcohols with Air-Stable Racemization Catalysts	p. 13
1.3.10 DKR of Secondary Alcohols with Racemization Catalyst 10	p. 14
1.3.11 DKR of Secondary Alcohols with Aluminum Catalysts	p. 14
1.3.12 DKR of Secondary Alcohols with Vanadium Catalysts	p. 15
1.4 Conclusions	p. 16
References	p. 17
2 Chemoenzymatic Routes to Enantiomerically Pure Amino Acids and Amines	p. 21
2.1 Introduction	p. 21
2.2 Amino Acids	p. 23
2.3 Amines	p. 33
References	p. 38
3 Oxidizing Enzymes in Multi-Step Biotransformation Processes	p. 41
3.1 Oxidizing Enzymes in Biocatalysis	p. 41
3.2 Classes of Oxidizing Enzymes	p. 41
3.3 Mechanisms of Biological Oxidation and Implications for Multi-Enzyme Biocatalysis	p. 44
3.4 Multi-Step Biotransformation Processes Involving Oxidation	p. 45
3.5 Design and Development of New Multi-Enzyme Oxidizing Processes	p. 48
3.5.1 Coupling Redox Enzymes	p. 48
3.5.2 Cofactor Recycle in Multi-Step Oxidizing Biocatalytic Systems	p. 51
3.6 Examples of Multi-Enzyme Biotransformation Processes Involving Oxidizing Enzymes	p. 52
3.6.1 Coupling of Oxidases with Non-Redox Enzymes	p. 53
3.6.2 Biocatalytic Systems Involving Coupled Oxidizing Enzymes	p. 53
3.7 Multi-Enzyme Systems in Whole-Cell Biotransformations and Expression of Redox Systems in Recombinant Hosts	p. 55
3.8 Other Applications of Multi-Enzyme Oxidizing Systems	p. 56
3.9 Conclusions	p. 58
References	p. 58
4 Dihydroxyacetone Phosphate-Dependent Aldolases in the Core of Multi-Step Processes	p. 61
4.1 Introduction	p. 61
4.2 DHAP-Dependent Aldolases	p. 63
4.2.1 Problem of DHAP Dependence	p. 63
4.2.2 DHAP-Dependent Aldolases in the Core of Aza Sugar Synthesis	p. 68
4.2.3 Combined Use of Aldolases and Isomerases for the Synthesis of Natural and Unnatural Sugars	p. 71
4.2.4 DHAP-Dependent Aldolases in the Synthesis of Natural Products	p. 73
4.3 Fructose-6-Phosphate Aldolase: An Alternative to DHAP-Dependent Aldolases?	p. 76
4.4 Conclusions	p. 78
References	p. 79
5 Multi-Enzyme Systems for the Synthesis of Glycoconjugates	p. 83
5.1 Introduction	p. 83
5.2 In Vitro and In Vivo Multi-Enzymes Systems	p. 85
5.3 Combinatorial Biocatalysis	p. 86
5.3.1 Synthesis and In Situ Regeneration of Nucleotide Sugars	p. 88
5.3.2 Synthesis of Oligosaccharides, Glycopeptides and Glycolipids Oligosaccharides	p. 94
5.4 Combinatorial Biosynthesis	p. 97
5.4.1 Synthesis of Oligosaccharides with Metabolically Engineered Cells	p. 98
5.5 Conclusions	p. 102
References	p. 102
6 Enzyme-Catalyzed Cascade Reactions	p. 109
6.1 Introduction	p. 109
6.2 Enzyme Immobilization	p. 110
6.3 Reaction Types: General Considerations	p. 111
6.4 Chiral Alcohols	p. 112
6.5 Chiral Amines	p. 114
6.6 Chiral Carboxylic Acid Derivatives	p. 121
6.7 C-C Bond Formation: Aldolases	p. 127
6.8 Oxidations with O[subscript 2] and H[subscript 2]O[subscript 2]	p. 130
6.9 Conclusions and Prospects	p. 131
References	p. 132
7 Multi-modular Synthases as Tools of the Synthetic Chemist	p. 137
7.1 Introduction	p. 137
7.2 Excised Domains for Chemical Transformations	p. 139
7.2.1 Function of Individual Domains and Domain Autonomy	p. 139
7.2.2 Heterocyclization and Aromatization	p. 139
7.2.3 Macrocyclization	p. 144
7.2.4 Halogenation	p. 147
7.2.5 Glycosylation	p. 150
7.2.6 Methyltransferases	p. 151
7.2.7 Oxidation	p. 153
7.3 Conclusions	p. 155
References	p. 156
8 Modifying the Glycosylation Pattern in Actinomycetes by Combinatorial Biosynthesis	p. 159
8.1 Bioactive Natural Products in Actinomycetes	p. 159
8.2 Deoxy Sugar Biosynthesis and Gene Clusters	p. 161
8.3 Characterization of Sugar Biosynthesis Enzymes	p. 161
8.4 Strategies for the Generation of Novel Glycosylated Derivatives	p. 165
8.4.1 Gene Inactivation	p. 165
8.4.2 Gene Expression	p. 166
8.4.3 Combining Gene Inactivation and Gene Expression	p. 166
8.4.4 Endowing a Host with the Capability of Synthesizing Different Sugars	p. 166
8.5 Generation of Glycosylated Derivatives of Bioactive Compounds	p. 166
8.5.1 Macrolides	p. 167
8.5.2 Aureolic Acid Group	p. 175
8.5.3 Angucyclines	p. 181
8.5.4 Anthracyclines	p. 186
8.5.5 Indolocarbazoles	p. 191
8.5.6 Aminocoumarins	p. 193
References	p. 194
9 Microbial Production of DNA Building Blocks	p. 199
9.1 Introduction	p. 199
9.2 Screening of Acetaldehyde-Tolerant Deoxyriboaldolase and Its Application for DR5P Synthesis	p. 200
9.3 Construction of Deoxyriboaldolase-Overexpressing E. coli and Metabolic Analysis of the E. coli Transformants for DR5P Production from Glucose and Acetaldehyde	p. 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	p. 203
9.5 Biochemical Retrosynthesis of 2'-Deoxyribonucleosides from Glucose Acetaldehyde and a Nucleobase: Three-Step Multi-Enzyme-Catalyzed Synthesis	p. 204
9.6 One-Pot Multi-Step Enzymatic Synthesis of 2'-Deoxyribonucleoside from Glucose, Acetaldehyde and a Nucleobase	p. 206
9.7 Improvement of the One-Pot Multi-Step Enzymatic Process for Practical Production of 2'-Deoxyribonucleoside from Glucose, Acetaldehyde and a Nucleobase	p. 207
9.8 Conclusions	p. 208
References	p. 210
10 Combination of Biocatalysis and Chemical Catalysis for the Preparation of Pharmaceuticals Through Multi-Step Syntheses	p. 213
10.1 Introduction: Biocatalysis and Chemical Catalysis	p. 213
10.2 Pharmaceuticals with Hydrolases	p. 214
10.2.1 Enzymatic Hydrolysis	p. 214
10.2.2 Enzymatic Transesterification	p. 219
10.2.3 Enzymatic Aminolysis	p. 222
10.3 Pharmaceuticals with Oxidoreductases	p. 226
10.4 Pharmaceuticals with Lyases	p. 227
10.5 Conclusions	p. 230
References	p. 231
Index	p. 235

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