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多聚物化学中的生物催化Biocatalysis in Polymer Chemistry(2011)
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这是关于生物催化合成聚合物的一本很不错的书，是Wiley上面的，里面每一章的都是这个领域的牛人所著，希望大家给我个五星级的评论啊 Preface XIII List of Contributors XIX List of Abbreviations XXIII 1 Monomers and Macromonomers from Renewable Resources 1 Alessandro Gandini 1.1 Introduction 1 1.2 Terpenes 2 1.3 Rosin 4 1.4 Sugars 6 1.5 Glycerol and Monomers Derived Therefrom 8 1.6 Furans 11 1.7 Vegetable Oils 16 1.8 Tannins 21 1.9 Lignin Fragments 23 1.10 Suberin Fragments 26 1.11 Miscellaneous Monomers 28 1.12 Conclusions 29 References 29 2 Enzyme Immobilization on Layered and Nanostructured Materials 35 Ioannis V. Pavlidis, Aikaterini A. Tzialla, Apostolos Enotiadis, Haralambos Stamatis, and Dimitrios Gournis 2.1 Introduction 35 2.2 Enzymes Immobilized on Layered Materials 36 2.2.1 Clays 36 2.2.1.1 Introduction 36 2.2.1.2 Enzymes Immobilization on Clays 38 2.2.2 Other Carbon Layered Materials 43 2.3 Enzymes Immobilized on Carbon Nanotubes 44 2.3.1 Introduction 44 2.3.2 Applications 45 2.3.3 Immobilization Approaches 46 Contents Biocatalysis in Polymer Chemistry. Edited by Katja Loos Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim ISBN: 978-3-527-32618-1 VI Contents 2.3.4 Structure and Catalytic Behavior of Immobilized Enzymes 50 2.4 Enzymes Immobilized on Nanoparticles 52 2.4.1 Introduction 52 2.4.2 Applications 53 2.4.3 Immobilization Approaches 55 2.4.4 Structure and Catalytic Behavior of Immobilized Enzymes 57 2.5 Conclusions 57 References 57 3 Improved Immobilization Supports for Candida Antarctica Lipase B 65 Paria Saunders and Jesper Brask 3.1 Introduction 65 3.2 Industrial Enzyme Production 66 3.2.1 Fermentation 66 3.2.2 Recovery and Purifi cation 66 3.2.3 Formulation 67 3.3 Lipase for Biocatalysis 67 3.3.1 Candida Antarctica Lipase B (CALB) 67 3.4 Immobilization 68 3.4.1 Novozym 435 69 3.4.2 NS81018 71 3.5 CALB- Catalyzed Polymer Synthesis 71 3.5.1 Polymerization 72 3.5.2 Polymer Separation and Purifi cation 72 3.5.3 Characterization and Performance Assays 73 3.5.4 CALB Immobilization 73 3.5.5 Results and Discussion 74 3.5.5.1 Effect of Synthesis Time on Molecular Weight 74 3.5.5.2 Comparison of NS 81018 and Novozym 435 75 3.5.5.3 Determination of Polycaprolactone Molecular Weight by GPC 75 3.5.5.4 Effect of Termination of Reaction 77 3.5.5.5 Effect of Solvent 78 3.5.5.6 Effect of Water 78 3.5.5.7 Effect of Immobilization Support 79 3.6 Conclusions 80 Acknowledgment 81 References 81 4 Enzymatic Polymerization of Polyester 83 Nemanja Miletic´, Katja Loos, and Richard A. Gross 4.1 Introduction 83 4.2 Synthesis of Polyesters 84 4.3 Enzyme-Catalyzed Polycondensations 85 4.3.1 A-B Type Enzymatic Polyesterfi cation 86 4.3.2 AA-BB Type Enzymatic Polyesterifi cation 92 4.3.3 Use of Activated Enol Esters for in vitro Polyester Synthesis 97 Contents VII 4.4 Enzyme-Catalyzed Ring-Opening Polymerizations 102 4.4.1 Unsubstituted Lactones 102 4.4.2 Substituted Lactones 109 4.4.3 Cyclic Ester Related Monomers 111 4.5 Enzymatic Ring-Opening Copolymerizations 113 4.6 Combination of Condensation and Ring-Opening Polymerization 121 4.7 Conclusion 122 References 123 5 Enzyme-Catalyzed Synthesis of Polyamides and Polypeptides 131 H. N. Cheng 5.1 Introduction 131 5.2 Catalysis via Protease 132 5.3 Catalysis via Lipase 134 5.4 Catalysis via Other Enzymes 136 5.5 Comments 137 References 138 6 Enzymatic Polymerization of Vinyl Polymers 143 Frank Hollmann 6.1 Introduction 143 6.2 General Mechanism and Enzyme Kinetics 143 6.3 Peroxidase-Initiated Polymerizations 146 6.3.1 Mechanism of Peroxidase-Initiated Polymerization 147 6.3.2 Infl uence of the Single Reaction Parameters 148 6.3.2.1 Enzyme Concentration 148 6.3.2.2 Hydrogen Peroxide Concentration 148 6.3.2.3 Mediator and Mediator Concentration 150 6.3.2.4 Miscellaneous 152 6.3.3 Selected Examples for Peroxidase-Initiated Polymerizations 153 6.4 Laccase-Initiated Polymerization 156 6.5 Miscellaneous Enzyme Systems 159 6.6 The Current State-of-the-Art and Future Developments 160 References 161 7 Enzymatic Polymerization of Phenolic Monomers 165 Hiroshi Uyama 7.1 Introduction 165 7.2 Peroxidase-Catalyzed Polymerization of Phenolics 165 7.3 Peroxidase-Catalyzed Synthesis of Functional Phenolic Polymers 170 7.4 Laccase-Catalyzed Polymerization of Phenolics 176 7.5 Enzymatic Preparation of Coatings 177 7.6 Enzymatic Oxidative Polymerization of Flavonoids 179 7.7 Concluding Remarks 182 References 182 VIII Contents 8 Enzymatic Synthesis of Polyaniline and Other Electrically Conductive Polymers 187 Rodolfo Cruz-Silva, Paulina Roman, and Jorge Romero 8.1 Introduction 187 8.2 PANI Synthesis Using Templates 188 8.2.1 Polyanion-Assisted Enzymatic Polymerization 188 8.2.2 Polycation-Assisted Templated Polymerization of Aniline 190 8.3 Synthesis of PANI in Template-Free, Dispersed and Micellar Media 192 8.3.1 Template-Free Synthesis of PANI 192 8.3.2 Synthesis in Dispersed Media 192 8.3.3 Enzymatic Synthesis of PANI Using Anionic Micelles as Templates 193 8.4 Biomimetic Synthesis of PANI 194 8.4.1 Hematin and Iron-Containing Porphyrins 194 8.4.2 Heme-Containing Proteins 195 8.5 Synthesis of PANI Using Enzymes Different From HRP 195 8.5.1 Other Peroxidases 196 8.5.2 Synthesis of PANI Using Laccase Enzymes 197 8.5.3 Synthesis of PANI Using Other Enzymes 198 8.6 PANI Films and Nanowires Prepared with Enzymatically Synthesized PANI 199 8.6.1 In Situ Enzymatic Polymerization of Aniline 199 8.6.2 Immobilization of HRP on Surfaces 200 8.6.2.1 Surface Confi nement of the Enzymatic Polymerization 200 8.6.2.2 Nanowires and Thin Films by Surface-Confi ned Enzymatic Polymerization 201 8.6.3 PANI Fibers Made with Enzymatically-Synthesized PANI 202 8.6.4 Layer-by-Layer and Cast Films of Enzymatically-Synthesized PANI 202 8.7 Enzymatic and Biocatalytic Synthesis of Other Conductive Polymers 203 8.7.1 Enzymatic and Biocatalytic Synthesis of Polypyrrole 203 8.7.2 Enzymatic and Biocatalytic Synthesis of Polythiophenes 205 8.8 Conclusions 207 References 207 9 Enzymatic Polymerizations of Polysaccharides 211 Jeroen van der Vlist and Katja Loos 9.1 Introduction 211 9.2 Glycosyltransferases 213 9.2.1 Phosphorylase 214 9.2.1.1 Enzymatic Polymerization of Amylose with Glycogen Phosphorylase 215 9.2.1.2 Hybrid Structures with Amylose Blocks 220 Contents IX 9.2.2 Branching Enzyme 224 9.2.3 Sucrase 227 9.2.4 Amylomaltase 228 9.2.5 Hyaluronan Synthase 229 9.3 Glycosidases 231 9.3.1 Cellulase 232 9.3.2 Hyaluronidase 234 9.3.3 Glycosynthases 236 9.4 Conclusion 237 References 238 10 Polymerases for Biosynthesis of Storage Compounds 247 Anna Bröker and Alexander Steinbüchel 10.1 Introduction 247 10.2 Polyhydroxyalkanoate Synthases 249 10.2.1 Occurrence of Polyhydroxyalkanoate Synthases 249 10.2.2 Chemical Structures of Polyhydroxyalkanoates and their Variants 250 10.2.3 Reaction Catalyzed by the Key Enzyme 251 10.2.4 Assay of Enzyme Activity 252 10.2.5 Location of Enzyme and Granule Structure 252 10.2.6 Primary Structures of the Enzyme 253 10.2.7 Special Motifs and Essential Residues 254 10.2.8 The Catalytic Mechanism of Polyhydroxyalkanoate Synthases 254 10.2.9 In Vitro Synthesis 255 10.2.10 Embedding in General Metabolism 255 10.2.11 Biotechnological Relevance 256 10.3 Cyanophycin Synthetases 257 10.3.1 Occurrence of Cyanophycin Synthetases 257 10.3.2 Chemical Structure of Cyanophycin 258 10.3.3 Variants of Cyanophycin 259 10.3.4 Reaction Catalyzed by the Key Enzyme 260 10.3.5 Assay of Enzyme Activity 260 10.3.6 Location of Enzyme–Granule Structure 261 10.3.7 Kinetic Data of Wild Type Enzyme 261 10.3.8 Primary Structures and Essential Motifs of the Enzyme 262 10.3.9 Catalytic Cycle 263 10.3.10 Mutant Variants of the Enzyme 265 10.3.11 In Vitro Synthesis 266 10.3.12 Embedding in General Metabolism 267 10.3.13 Biotechnological Relevance 267 10.4 Conclusions 268 References 268 X Contents 11 Chiral Polymers by Lipase Catalysis 277 Anja Palmans and Martijn Veld 11.1 Introduction 277 11.2 Reaction Mechanism and Enantioselectivity of Lipases 278 11.3 Lipase-catalyzed Synthesis and Polymerization of Optically Pure Monomers 280 11.4 Kinetic Resolution Polymerization of Racemic Monomers 284 11.4.1 KRP of Linear Monomers 284 11.4.2 KRP of Substituted Lactones 286 11.5 Dynamic Kinetic Resolution Polymerization of Racemic Monomers 287 11.5.1 Dynamic Kinetic Resolutions in Organic Chemistry 288 11.5.2 Extension of Dynamic Kinetic Resolutions to Polymer Chemistry 289 11.5.3 Dynamic Kinetic Resolution Polymerizations 290 11.5.4 Iterative Tandem Catalysis: Chiral Polymers from Racemic ω-Methylated Lactones 294 11.6 Tuning Polymer Properties with Chirality 296 11.6.1 Chiral Block Copolymers Using Enzymatic Catalysis 296 11.6.2 Enantioselective Acylation and Deacylation on Polymer Backbones 299 11.6.3 Chiral Particles by Combining eROP and Living Free Radical Polymerization 300 11.7 Conclusions and Outlook 301 References 301 12 Enzymes in the Synthesis of Block and Graft Copolymers 305 Steven Howdle and Andreas Heise 12.1 Introduction 305 12.2 Synthetic Strategies for Block Copolymer Synthesis Involving Enzymes 306 12.2.1 Enzymatic Polymerization from Functional Polymers (Macroinitiation) 307 12.2.2 Enzymatic Synthesis of Macroinitiators Followed by Chemical Polymerization 310 12.2.2.1 Dual Initiator Approach 310 12.2.2.2 Modifi cation of Enzymatic Blocks to Form Macroinitiators 316 12.3 Enzymatic Synthesis of Graft Copolymers 319 12.4 Summary and Outlook 320 References 320 13 Biocatalytic Polymerization in Exotic Solvents 323 Kristofer J. Thurecht and Silvia Villarroya 13.1 Supercritical Fluids 324 Contents XI 13.1.1 Lipase-catalyzed Homopolymerizations 326 13.1.2 Lipase-catalyzed Depolymerization (Degradation) 328 13.1.3 Combination of Polymerization Mechanisms: Polymerization from Bifunctional Initiators 329 13.1.4 Free Radical Polymerization Using Enzymatic Initiators 333 13.2 Biocatalytic Polymerization in Ionic Liquids 334 13.2.1 Free Radical Polymerization 334 13.2.2 Lipase-catalyzed Polymerization in Ionic Liquids 337 13.3 Enzymatic Polymerization under Biphasic Conditions 339 13.3.1 Ionic Liquid-Supported Catalyst 340 13.3.2 Biphasic Polymerization of Polyphenols 342 13.3.3 Fluorous Biphasic Polymerization 342 13.4 Other ‘Exotic’ Media for Biocatalytic Polymerization 342 13.5 Conclusion 343 References 343 14 Molecular Modeling Approach to Enzymatic Polymerization 349 Gregor Fels and Iris Baum 14.1 Introduction 349 14.2 Enzymatic Polymerization 352 14.3 Candida antarctica Lipase B – Characterization of a Versatile Biocatalyst 353 14.4 Lipase Catalyzed Alcoholysis and Aminolysis of Esters 354 14.5 Lipase-Catalyzed Polyester Formation 357 14.6 CALB -Catalyzed Polymerization of β-Lactam 357 14.7 General Remarks 367 References 367 15 Enzymatic Polymer Modifi cation 369 Georg M. Guebitz 15.1 Introduction 369 15.2 Enzymatic Polymer Functionalization: From Natural to Synthetic Materials 369 15.3 Surface Hydrolysis of Poly(alkyleneterephthalate)s 370 15.3 1 Enzymes and Processes 370 15.3.2 Mechanistic Aspects 372 15.3.3 Surface Analytical Tools 375 15.4 Surface Hydrolysis of Polyamides 376 15.4.1 Enzymes and Processes 376 15.4.2 Mechanistic Aspects 377 15.5 Surface Hydrolysis of Polyacrylonitriles 378 15.6 Future Developments 380 Acknowledgment 380 References 381 XII Contents 16 Enzymatic Polysaccharide Degradation 389 Maricica Munteanu and Helmut Ritter 16.1 The Features of the Enzymatic Degradation 389 16.2 Enzymatic Synthesis and Degradation of Cyclodextrin 390 16.2.1 Cyclodextrins: Structure and Physicochemical Properties 390 16.2.1.1 The Discovery Period from 1891–1935 392 16.2.1.2 The Exploratory Period from 1936–1970 392 16.2.1.3 The Utilization Period: from 1970 Onward 392 16.2.2 Cyclodextrin Synthesis via Enzymatic Degradation of Starch 392 16.2.2.1 Cyclodextrin Glycosyltransferases: Structure and Catalytic Activity 393 16.2.2.2 Cyclodextrin Glycosyltransferase: Cyclodextrin-Forming Activity 394 16.2.2.3 Other Industrial Applications of Cyclodextrin Glycosyltransferase 397 16.2.3 Cyclodextrin Hydrolysis 398 16.2.3.1 Acidic Hydrolysis of Cyclodextrin 399 16.2.3.2 Cyclodextrin Enzymatic Degradation 400 16.2.3.3 Cyclodextrin Degradation by the Intestinal Flora 404 16.2.4 Enzymatic Synthesis of Cyclodextrin-Derivatives 405 16.2.5 Cyclodextrin-Based Enzyme Mimics 405 16.2.6 Specifi c-Base-Catalyzed Hydrolysis 406 16.3 Hyaluronic Acid Enzymatic Degradation 406 16.3.1 Hyaluronic Acid: Structure, Biological Functions and Clinical Applications 406 16.3.2 Hyaluronidase: Biological and Clinical Signifi cance 408 16.4 Alginate Enzymatic Degradation 409 16.4.1 Alginate as Biocompatible Polysaccharide 409 16.4.2 Alginate Depolymerization by Alginate Lyases 411 16.5 Chitin and Chitosan Enzymatic Degradation 411 16.5.1 Enzymatic Hydrolysis of Chitin 411 16.5.2 Enzymatic Hydrolysis of Chitosan 413 16.6 Cellulose Enzymatic Degradation 414 16.7 Conclusion 415 References 415[ Last edited by danghaichun on 2012-4-24 at 10:18 ] |
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