Biotransformations in Organic Chemistry : A Textbook By Faber, Kurt

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Biotransformations in Organic Chemistry

A Textbook

Faber, Kurt

6th ed. 2011. 6th revised and corrected edition, XI, 423 p. 347 illus., 335 illus. in color.

 

 

  • First textbook on biotransformations
  • Remains the established text in the field
  • More and more courses are taught on this subject at universities worldwide
  • 6th edition is didactically improved by including color graphics
  • New edition includes chapters on fresh developments

The use of biocatalysts, employed either as isolated enzymes or whole microbial cells, offers a remarkable arsenal of highly selective transformations for state-of-the-art synthetic organic chemistry. Over the last two decades, this methodology has become an indispensable tool for asymmetric synthesis, not only at the academic level, but also on an industrial scale.

This well-established textbook on biocatalysis provides a basis for undergraduate and graduate courses in modern organic chemistry, as well as a condensed introduction into this field. After a basic introduction into the use of biocatalysts—principles of stereoselective transformations, enzyme properties and kinetics—the different types of reactions are explained according to the 'reaction principle', such as hydrolysis, reduction, oxidation, C–C bond formation, etc. Special techniques, such as the use of enzymes in organic solvents, immobilization techniques and modified or artificial enzymes, are treated in a separate section. A final chapter deals with thebasic rules for the safe and practical handling of biocatalysts.

In this completely revised 6th edition, emphasis has been given to an improved didactic style including colored graphics in order to facilitate a deeper understanding of the underlying principles. New developments, such as transamination, enzyme promiscuity and applications on industrial scale within the field of 'white biotechnology' are included.

Content Level » Graduate

Keywords » Biocatalysis Biotechnology Biotransformation Enzymes Organic Chemistry -Whole Cells

 

 

1 Introduction and Background Information .............................. 1
1.1 Introduction ............................................................. 1
1.2 Common Prejudices Against Enzymes ................................. 2
1.3 Advantages and Disadvantages of Biocatalysts ........................ 3
1.3.1 Advantages of Biocatalysts ..................................... 3
1.3.2 Disadvantages of Biocatalysts ................................... 7
1.3.3 Isolated Enzymes vs. Whole Cell Systems ..................... 9
1.4 Enzyme Properties and Nomenclature . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 11
1.4.1 Structural Biology in a Nutshell . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 11
1.4.2 Mechanistic Aspects of Enzyme Catalysis . . . . . . . . . . . . . . . . . . . . 13
1.4.3 Classification and Nomenclature . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 23
1.4.4 Coenzymes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 26
1.4.5 Enzyme Sources . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 27
References . .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 27
2 Biocatalytic Applications . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 
2.1 Hydrolytic Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 31
2.1.1 Mechanistic and Kinetic Aspects . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 31
2.1.2 Hydrolysis of the Amide Bond . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 51
2.1.3 Ester Hydrolysis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 60
2.1.4 Hydrolysis and Formation of Phosphate Esters . . . . . . . . . . . . . . 111
2.1.5 Hydrolysis of Epoxides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 120
2.1.6 Hydrolysis of Nitriles . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 130
2.2 Reduction Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 139
2.2.1 Recycling of Cofactors . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 140
2.2.2 Reduction of Aldehydes and Ketones Using
Isolated Enzymes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 145
2.2.3 Reduction of Aldehydes and Ketones Using Whole Cells . . 153
2.2.4 Reduction of C¼C-Bonds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 166
2.3 Oxidation Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 173
2.3.1 Oxidation of Alcohols and Aldehydes . . . . . . . . . . . . . . . . . . . . . . . 173
2.3.2 Oxygenation Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 176
2.3.3 Peroxidation Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 204
2.4 Formation of Carbon–Carbon Bonds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 211
2.4.1 Aldol Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 211
2.4.2 Thiamine-Dependent Acyloin and Benzoin Reactions . . . . . . 225
2.4.3 Michael-Type Additions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 231
2.5 Addition and Elimination Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 233
2.5.1 Cyanohydrin Formation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 233
2.5.2 Addition of Water . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 237
2.5.3 Addition of Ammonia . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 240
2.6 Transfer Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 242
2.6.1 Glycosyl Transfer Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 242
2.6.2 Amino Transfer Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 254
2.7 Halogenation and Dehalogenation Reactions .. . . . . . . . . . . . . . . . . . . . . . . 257
2.7.1 Halogenation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 258
2.7.2 Dehalogenation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 263
References . .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 268
3 Special Techniques . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 315
3.1 Enzymes in Organic Solvents . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 315
3.1.1 Ester Synthesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 324
3.1.2 Lactone Synthesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 342
3.1.3 Amide Synthesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 343
3.1.4 Peptide Synthesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 346
3.1.5 Peracid Synthesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 351
3.1.6 Redox Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 352
3.1.7 Medium Engineering . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 354
3.2 Immobilization . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 356
3.3 Artificial and Modified Enzymes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 367
3.3.1 Artificial Enzyme Mimics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 367
3.3.2 Modified Enzymes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 368
3.3.3 Catalytic Antibodies . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 373
References . .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 377
4 State of the Art and Outlook . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 391
References . .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 396
5 Appendix . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 397
5.1 Basic Rules for Handling Biocatalysts . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 397
5.2 Abbreviations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 400
5.3 Suppliers of Enzymes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 401
x Contents5.4 Commonly Used Enzyme Preparations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 402
5.5 Major Culture Collections . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 404
5.6 Pathogenic Bacteria and Fungi . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 405
Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 407

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