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Biocatalysts in Organic Synthesis Book

Biocatalysts in Organic Synthesis
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  • Biocatalysts in Organic Synthesis
  • Written by author Jan Halgas
  • Published by Elsevier Science Ltd, 1992/10/01
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Introduction
Abbreviations
1 Enzymes - Catalysts of Life 1
1.1 Classification of enzymes 2
1.2 Principles of the kinetics of enzymatic reactions 3
1.2.1 Inhibitors, inhibition with substrate and product 5
1.3 Effects of organic solvents on enzymes 7
1.4 Effects of temperature and pH on the stability and activity of enzymes 11
1.5 Units of enzymatic activity 12
2 The Biocatalyst Form 13
2.1 Free enzymes 13
2.1.1 Characteristics of free enzymes 14
2.1.2 Modified enzymes 14
2.2 Immobilized enzymes 17
2.2.1 Methods of the enzyme immobilization 18
2.2.2 Properties of immobilized enzymes 33
2.3 Cells of microorganisms 35
2.3.1 Transformations by growing cells 36
2.3.2 Transformations by preliminarily grown cells 36
2.4 Immobilized cells of microorganisms 37
2.4.1 Methods of cell immobilization 38
2.4.2 Simultaneous immobilization of several biocatalysts 40
2.5 Plant and animal cells 40
2.6 Non-enzymatic biopreparations 42
3 Biocatalysts and the Problem of Selectivity in Organic Synthesis 46
3.1 Specificity of chemical action and substrate specificity of enzymes 47
3.2 Differentiation of enantiomers 47
3.3 Differentiation of enantiotopic groups 52
3.4 Differentiation of enantiotopic sides 54
4 Substitution Reactions Using Biocatalysts 58
4.1 Methylations 58
4.2 Halogenations 59
4.3 Substitution reactions in the side chain of amino acids 62
4.4 Substitutions on aromatic systems with the formation of a C=C bond 65
4.5 Substitutions at C-1 in saccharides 66
5 Elimination and Addition Reactions 70
5.1 Additions to the C=C bond 70
5.2 Additions to the C=O bond 78
6 Syntheses and Hydrolyses of Esters 91
6.1 Syntheses of esters 91
6.2 Chemo- and regioselective hydrolyses of esters 104
6.3 Kinetic resolutions of racemic esters, acids and alcohols 109
6.3.1 Hydrolysis and transesterification of esters of racemic acids 109
6.3.2 Resolution of racemic alcohols through esters 127
6.4 Diesters of prochiral dicarboxylic acids 162
6.5 Prochiral diols 177
7 Syntheses and Hydrolyses of Amides 188
7.1 Syntheses of amides and peptides 188
7.2 Hydrolyses of amides and nitriles 198
8 Oxidations 208
8.1 Oxidation of alcohols 208
8.2 Further oxidation reactions 220
8.2.1 The Baeyer-Villiger oxidation 220
8.2.2 Hydroxylations 223
8.2.3 Dehydrogenations of the CH-CH bond 229
8.2.4 Oxidations of amino acids to oxo acids 230
8.2.5 Oxidations of nitrogenous heterocyclic compounds 232
8.2.6 Oxidations on nitrogen, sulphur or selenium atoms 233
9 Reductions 236
9.1 Reductions of aldehydes and acyclic ketones 237
9.2 Reductions of cyclic ketones 252
9.3 Reductions of di- and tricarbonyl compounds 258
9.4 Reductions of oxo acids, oxo esters and oxo amides 270
9.5 Reductions of the carbonyl group in organometallic compounds 288
9.6 Reductions of the C=C bond 291
9.7 Syntheses of [alpha]-amino acids from [alpha]-oxo acids 294
9.8 Reductions of the nitro group 297
9.9 Miscellaneous reductions 298
References 301
Subject index 329


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