Asymmetric organic synthesis with enzymes:
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| Format: | Book |
|---|---|
| Language: | English |
| Published: |
Weinheim
WILEY-VCH
2008
|
| Subjects: | |
| Online Access: | Inhaltstext Inhaltsverzeichnis |
| Physical Description: | XIV, 325 S. Ill., graph. Darst. 240 mm x 170 mm |
| ISBN: | 9783527318254 3527318259 |
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MARC
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| 245 | 1 | 0 | |a Asymmetric organic synthesis with enzymes |c ed. by Vicente Gotor ... |
| 264 | 1 | |a Weinheim |b WILEY-VCH |c 2008 | |
| 300 | |a XIV, 325 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 Asymmetric synthesis | |
| 650 | 4 | |a Enzymes |x Synthesis | |
| 650 | 4 | |a Organic compounds |x Synthesis | |
| 650 | 0 | 7 | |a Enzymkatalyse |0 (DE-588)4152480-9 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Asymmetrische Synthese |0 (DE-588)4135603-2 |2 gnd |9 rswk-swf |
| 689 | 0 | 0 | |a Asymmetrische Synthese |0 (DE-588)4135603-2 |D s |
| 689 | 0 | 1 | |a Enzymkatalyse |0 (DE-588)4152480-9 |D s |
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| 700 | 1 | |a Gotor, Vicente |e Sonstige |0 (DE-588)134010639 |4 oth | |
| 856 | 4 | 2 | |q text/html |u http://deposit.dnb.de/cgi-bin/dokserv?id=2982596&prov=M&dok_var=1&dok_ext=htm |3 Inhaltstext |
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Record in the Search Index
| _version_ | 1805089677752926208 |
|---|---|
| adam_text |
1.1 1.2 1.2.1 1.2.2 1.2.2.1 1.2.2.2 1.2.2.3 1.2.3 1.2.4 1.2.4.1 1.2.4.2
1.3 2 2.1 2.2 2.3 CONTENTS PREFACE XL LIST OF CONTRIBUTORS XIII
METHODOLOGY MEDIUM ENGINEERING 3 GIACOMO CARREA AND SERGIO RIVA
INTRODUCTION 3 MODULATION OF ENZYME ENANTIOSELECTIVITY BY MEDIUM
ENGINEERING 5 SELECTIVITY ENHANCEMENT BY ADDITION OFWATER-MISCIBLE
ORGANIC COSOLVENTS 5 SELECTIVITY ENHANCEMENT IN ORGANIC MEDIA WITH LOW
WATER ACTIVITY 7 ORGANIC SOLVENT SYSTEMS 7 ENZYME PROPERTIES IN ORGANIC
SOLVENTS 8 MEDIUM ENGINEERING 9 RATIONALES 12 MODULATION OF ENZYME
SELECTIVITY: NEW TRENDS OF RESEARCH 14 IONIC LIQUIDS 14 ADDITIVES 16
CONDUSIONS AND OUTLOOKS 17 REFERENCES 17 DIREETED EVOLUTION AS A MEANS
TO ENGINEER ENANTIOSELEETIVE ENZYMES 21 MANFRED T. REETZ INTRODUCTION 21
MOLECULAR BIOLOGICAL METHODS FOR MUTAGENESIS 23 HIGH-THROUGHPUT
SCREENING METHODS FOR ENANTIOSELECTIVITY 27 ASYMMETRIE ORGA"IE SY"THESIS
WITH IIHZYMES. EDITED BY VICENTE GOTOR, JGNACIO ALFONSO. AND EDUARDO
GARCIA-URDIALES COPYRIGHT 2008 WILEY-VCH VERLAG GMBH & CO. KGAA,
WEINHEIM [SBN: 978-3-527-31825-4 3 VI I CONTENTS 2.4 2.4.1 2.4.2 2.4.3
2.4.4 2.4.5 2.4.6 2.4.7 2.4.8 2.4.9 2.4.10 2.4.11 2.4.12 2.4.13 2.5 3.1
3.2 3.2.1 3.2.2 3.2.3 3.3 3.3.1 3.3.1.1 3.3.1.2 3.3.1.3 3.3.1.4 3.3.2
3.3.2.1 3.3.2.2 3.3.2.3 3.3.2.4 3.3.2.5 3.3.2.6 3.3.2.7 3.3.2.8 3.4
EXAMPLES OF ENHANCING THE ENANTIOSELECTIVITY OF ENZYMES BY* DIRECTED
EVOLUTION 28* LIPASE FROM PSEUDOMONAS AERUGINOSA (PAL) 28* OTHER LIPASES
38* ESTERASES 38* HYDANTOINASES 39* NITRILASES 39* EPOXIDE HYDROLASES
41* PHOSPHOTRIESTERASES 45* AMINOTRANSFERASES 45* ALDOLASES 46*
CYCLOHEXANONE AND CYCLOPENTANONE MONOOXYGENASES AS* BAEYER-VILLIGERASES
AND SULFOXIDATION CATALYSTS 48* MONOAMINE OXIDASES 54* CYTOCHROME P450
ENZYMES 55* OTHER ENZYMES 55* CONCLUSIONS AND PERSPECTIVES 56*
REFERENCES 56* THE SEARCH FOR NEW ENZYMES 65* JEAN-LOUIS REYMOND AND
WOLFGANG STREIT* INTRODUCTION 65* MECHANISM-BASED ENZYME DESIGN THE
GENOMES OF NOT YET CULTURED MICROBES AS RESOURCES* 66* CATALYTIC
ANTIBODIES 66* RATIONAL DESIGN OF NEW CATALYSTS ON ENZYME AND PROTEIN
BASIS 69* SYNTHETIC ENZYME MODELS 71* METAGENOMICS 71* CONSTRUCTION OF
METAGENOME-DERIVED DNA LIBRARIES 72* SELECTION OF THE ENVIRONMENT 72*
CLONING STRATEGIES 73* SCREENING AND DETECTION TECHNOLOGIES 73* MAJOR
PROBLEMS THAT NEED TO BE ADDRESSED 74* FOR NOVEL GENES 75*
POLYSACCHARIDE DEGRADINGJMODIFYING ENZYMES 75* LIPOLYTIC BIOCATALYSTS
77* VITAMIN BIOSYNTHESIS 77* NITRILASES, NITRILE HYDRATASES, AND
AMIDASES 78* OXIDOREDUCTASESJDEHYDROGENASES 79* PROTEASES 79* GLYCEROL
HYDRATASES 79* ANTIBIOTICS AND PHARMACEUTICALS 79* CONCLUSION 80*
REFERENCES 80* CONTENTS I VII* 11* SYNTHETIC APPLICATIONS 87* 4* DYNAMIC
KINETIC RESOLUTIONS 89* BELEN MARTIN-MATUTE AND JAN-E. BAECKVALL 4.1*
INTRODUETION 89* 4.1.1* SYNTHESIS OF ENANTIOMERICALLY PURE COMPOUNDS 89*
4.1.2* KINETIC RESOLUTION (KR) AND DYNAMIC KINETIC* RESOLUTION (DKR) 90*
4.1.3* ENZYMES IN ORGANIC CHEMISTRY 91* 4.2* METAL-CATALYZED
RACEMIZATION 92* 4.2.1* DKR OF ALLYLIC ACETATES AND ALLYLIC ALCOHOLS 93*
4.2.2* DKR OF SEC-ALCOHOLS 94* 4.2.3* DKR OF AMINES 98* 4.3*
BASE-CATALYZED RACEMIZATION 98* 4.3.1* DKR OFTHIOESTERS 99* 4.3.2* DKR
OF ACTIVATED ESTERS LOO 4.3.3* DKR OF OXAZOLONES LOO 4.3.4* DKR OF
HYDANTOINS 101* 4.3.5* DKR OF ACYLOINS LOL 4.4* ACID*CATALYZED
RACEMIZATION LOL 4.5* RACEMIZATION THROUGH CONTINUOUS REVERSIBLE
FORMATION-CLEAVAGE OF THE SUBSTRATE LO2 4.5.1* DKR OF CYANOHYDRINS 103*
4.5.2* DKR OF HEMITHIOATHETALS LO3 4.6* RACEMIZATION CATALYZED BY
ALDEHYDES 104* 4.7* ENZYME-CATALYZED RACEMIZATION LO6 4.8* RACEMIZATION
THROUGH S N 2 DISPLACEMENT 106* 4.9* OTHER RACEMIZATION METHODS 107*
4.9.1* DKR OF 5-HYDROXY-2-(5H)-FURANONES 107* 4.9.2* DKR OF HEMIAMINALS
LO7 4.9.3* DKR OF 8-AMINO-5,6,7,8-TETRAHYDROQUINOLINE 108* 4.10*
CONCLUDING REMARKS LO9 REFERENCES 1LO 5* DERACEMIZATION AND
ENANTIOCONVERGENT PROCESSES 115* NICHOLASJ. TURNER 5.1* INTRODUCTION
115* 5.2* DERACEMIZATION PROCESSES 116* 5.2.1* CYCLIC
OXIDATION-REDUCTION SYSTEMS 116* 5.2.2* MICROBIAL DERACEMIZATION OF
SECONDARY ALCOHOLS USING A SINGLE* MICROORGANISM 122* 5.2.3*
DERACEMIZATION OF ALCOHOLS USING TWO ENZYMEJMICROORGANISM* SYSTEMS 124*
5.2.4* EPOXIDES 126* VIII I CONTENTS 5.2.5 5.3 5.3.1 5.3.2 5.4 6* 6.1
6.1.1 6.1.2 6.1.3 6.1.4 6.2 6.2.1 6.2.2 6.2.3 6.2.4 6.2.5 6.2.6 6.2.7
6.3 6.4 6.5 7* 7.1 7.2 7.3 7.4 7.4.1 7.4.2 7.4.3 7.4.4 7.5 7.6 7.7
CARBOXYLIC ACIDS 126* ENANTIOCONVERGENT PROCESSES 127* EPOXIDE
HYDROLYSIS 128* SULFATASES 129* CONCLUSIONS AND FUTURE PROSPECTS 130*
REFERENCES 130* TRANSESTERIFICATION AND HYDROLYSIS OF CARBOXYLIC* ACID
DERIVATIVES, ALCOHOLS, AND EPOXIDES 133* ROBERT CHENEVERT, PIERRE MORIN,
AND NICHOLAS PELCHAT LNTRODUCTION AND GENERAL ASPECTS 133* KINETIC
RESOLUTION, DYNAMIC KINETIC RESOLUTION, AND* ENANTIOSELECTIVE
BIOTRANSFORMATIONS OF CARBOXYLIC* SCOPE 133* REACTION CONDITIONS 133*
DESYMMETRIZATION 134* ENANTIOCONVERGENT TRANSFORMATION 137* ACID
DERIVATIVES 137* ESTER HYDROLYSIS 137* ESTER ALCOHOLYSIS 140*
ESTERIFICATION OF CARBOXYLIC ACIDS 140* LACTONES 142* ANHYDRIDES 143*
HYDROLYSIS OFNITRILES 144* HYDROLYSIS OF AMIDES, LACTAMS, AND HYDANTOINS
146* ENANTIOSELECTIVE ENZYMATIC TRANSFORMATIONS OF ALCOHOLS 150*
HYDROLYSIS OF EPOXIDES 157* CONCLUSION 162* REFERENCES 163* AMINOLYSIS
AND AMMONOLYSIS OFCARBOXYLIC ACID DERIVATIVES 171* VICENTE
GOTOR-FERNANDEZ AND VICENTE GOTOR INTRODUCTION 171* MECHANISM OF
ENZYMATIC AMMONOLYSIS AND AMINOLYSIS* REACTIONS 172* AMINOLYSIS AND
AMMONOLYSIS OF CARBOXYLIC ACIDS 174* AMINOLYSIS AND AMMONOLYSIS OF
ESTERS 176* PREPARATION OFNONCHIRAL AMIDES 176* RESOLUTION OF ESTERS
178* RESOLUTION OF AMINES, DIAMINES, AND AMINOALCOHOLS 180*
DESYMMETRIZATION OF DIESTERS 184* KINETIC RESOLUTION OF SECONDARY AMINES
185* TOWARD THE SYNTHESIS OF SS-AMINOACID DERIVATIVES 186* SUMMARY AND
OUTLOOK 188* REFERENCES 189* 8 8.1 8.2 8.2.1 8.2.2 8.2.3 8.2.4 8.2.5
8.2.6 8.3 8.3.1 8.3.2 8.3.2.1 8.3.2.2 8.3.2.3 8.3.2.4 8.3.3 8.3.4
8.3.4.1 8.3.4.2 8.3.4.3 8.4 8.4.1 8.4.1.1 8.4.1.2 8.4.2 8.4.3 8.4.4 8.5
8.5.1 8.5.2 8.5.3 8.5.3.1 8.5.3.2 8.6 9* 9.1 9.2 9.2.1 9.2.2 CONTENTS
IIX ENZYMATIC REDUCTION REACTION 193* KAORU NAKAMURA AND TOMOKO MATSUDA
INTRODUCTION 193* HYDROGEN SOURCE FOR COENZYME REGENERATION 193* ALCOHOL
AS A HYDROGEN SOURCE OFREDUCTION 194* SUGAR AS A HYDROGEN SOURCE OF
REDUCTION 194* FORMATE AS A HYDROGEN SOURCE OF REDUCTION 194* MOLECULAR
HYDROGEN AS A HYDROGEN SOURCE OF REDUCTION 195* LIGHT ENERGY AS A
HYDROGEN SOURCE OF REDUCTION 196* ELECTRIC POWER AS A HYDROGEN SOURCE OF
REDUCTION 198* METHODOLOGY FOR STEREOCHEMICAL CONTROL 199* SCREENING OF
MICROBES 199* MODIFICATION OF BIOCATALYSTS BY GENETIC METHODS 201*
MODIFIED YEAST 201* OVEREXPRESSION 202* COEXPRESSION OF GENES FOR
CARBONYJ REDUCTASE AND COFACTOR-REGENERATING ENZYMES 203* MODIFICATION
OF BIOCATALYSTS: DIRECTED EVOLUTION 204* MODIFICATION OF SUBSTRATES 205*
MODIFICATION OF REACTION CONDITIONS 206* ACETONE TREATMENT OF THE CELL
206* SELECTIVE INHIBITOR 207* REACTION TEMPERATURE 208* MEDIUM
ENGINEERING 209* ORGANIC SOLVENT 209* SOLUBLE ORGANIC SOLVENT 209*
AQUEOUS-ORGANIC TWO-PHASE REACTION 209* USE OF HYDROPHOBIC RESIN, XAD
211* SUPERCRITICAL CARBON DIOXIDE 213* IONIC LIQUID 215* SYNTHETIC
APPLICATIONS 216* REDUCTION OF ALDEHYDE 216* REDUCTION OF KETONE 216*
DYNAMIC KINETIC RESOLUTION AND DERACEMIZATION 221* DYNAMIC KINETIC
RESOLUTION 221* DERACEMIZATION THROUGH OXIDATION AND REDUCTION 223*
CONCLUSIONS 224* REFERENCES 225* BIOOXIDATIONS IN CHIRAL SYNTHESIS 229*
MARKO D. MIHOVILOVIC AND DARIO A. BIANCHI* INTRODUCTION 229* OXIDATIONS
OF AICOHOLS AND AMINES 231* REGIOSELECTIVE OXIDATION OF AICOHOLS 231*
DESYMMETRIZATIONS OF DIOLS 233* X I CONTENTS 9.2.3 9.2.4 9.2.5 9.3 9.3.1
9.3.2 9.3.3 9.4 9.5 9.5.1 9.5.2 9.5.3 9.5.4 9.6 9.6.1 9.6.2 9.6.3 9.7
9.7.1 9.7.2 9.8 9.9 10* 10.1 10.2 10.3 10.3.1 10.3.2 10.4 10.4.1 10.4.2
10.4.3 10.5 10.6. 10.7 10.8 KINETIC RESOLUTION OF PRIMARY AND SECONDARY
ALCOHOLS 234* DERACEMIZATION OF SECONDARY ALCOHOLS 235* DERACEMIZATION
OF AMINES 237* OXYGENATION OFNONACTIVATED CARBON CENTERS 237*
HYDROXYLATIONS BY WILD-TYPE WHOLE-CELLS 238* HYDROXYLATIONS BY
RECOMBINANT CYTOCHROME P450* MONOOXYGENASES 239* HYDROXYLATION VIA
HYDROPEROXIDE FORMATION 241* ENZYMATIC EPOXIDATION 241* BAEYER-VILLIGER
OXIDATIONS 243* CHEMOSELECTIVITY 245* DESYMMETRIZATIONS 246* KINETIC
RESOLUTIONS 248* REGIODIVERGENT BIOOXIDATIONS 251* HETEROATOM OXIDATIONS
253* SULFIDE OXIDATION 253* OXIDATION OF DITHIO-COMPOUNDS 256* OXIDATION
OF OTHER HETEROATOMS 256* ARYL DIHYDROXYLATIONS 257* DIOXYGENATION IN
ORTHO- AND META-POSITION 257* DIOXYGENATION IN IPSO- AND ORTHO-POSITION
262* HALOGENATION REACTIONS 263* SUMMARY AND OUTLOOK 265* REFERENCES
265* ALDOLASES: ENZYMES FOR MAKING AND BREAKING C-C BONDS 275*
WOLF-OIETER FESSNER INTRODUCTION 275* MECHANISTIC CLASSIFICATION 276*
PYRUVATE ALDOLASES 278* N-ACETYLNEURAMINIC ACID ALDOLASE 278* RELATED
PYRUVATE ALDOLASES 281* DIHYDROXYACETONE PHOSPHATE ALDOLASES 284*
FRUCTOSE 1,6-BISPHOSPHATE ALDOLASE 285* RELATED DHAP ALDOLASES 286*
PREPARATIVE APPLICATIONS 288* TRANSKETOLASE AND RELATED ENZYMES 302*
2-DEOXY-D-RIBOSE 5-PHOSPHATE ALDOLASE 305* GLYCINE ALDOLASES 308*
SUMMARY 311* REFERENCES 311* INDEX 319* |
| adam_txt |
1.1 1.2 1.2.1 1.2.2 1.2.2.1 1.2.2.2 1.2.2.3 1.2.3 1.2.4 1.2.4.1 1.2.4.2
1.3 2 2.1 2.2 2.3 CONTENTS PREFACE XL LIST OF CONTRIBUTORS XIII
METHODOLOGY MEDIUM ENGINEERING 3 GIACOMO CARREA AND SERGIO RIVA
INTRODUCTION 3 MODULATION OF ENZYME ENANTIOSELECTIVITY BY MEDIUM
ENGINEERING 5 SELECTIVITY ENHANCEMENT BY ADDITION OFWATER-MISCIBLE
ORGANIC COSOLVENTS 5 SELECTIVITY ENHANCEMENT IN ORGANIC MEDIA WITH LOW
WATER ACTIVITY 7 ORGANIC SOLVENT SYSTEMS 7 ENZYME PROPERTIES IN ORGANIC
SOLVENTS 8 MEDIUM ENGINEERING 9 RATIONALES 12 MODULATION OF ENZYME
SELECTIVITY: NEW TRENDS OF RESEARCH 14 IONIC LIQUIDS 14 ADDITIVES 16
CONDUSIONS AND OUTLOOKS 17 REFERENCES 17 DIREETED EVOLUTION AS A MEANS
TO ENGINEER ENANTIOSELEETIVE ENZYMES 21 MANFRED T. REETZ INTRODUCTION 21
MOLECULAR BIOLOGICAL METHODS FOR MUTAGENESIS 23 HIGH-THROUGHPUT
SCREENING METHODS FOR ENANTIOSELECTIVITY 27 ASYMMETRIE ORGA"IE SY"THESIS
WITH IIHZYMES. EDITED BY VICENTE GOTOR, JGNACIO ALFONSO. AND EDUARDO
GARCIA-URDIALES COPYRIGHT 2008 WILEY-VCH VERLAG GMBH & CO. KGAA,
WEINHEIM [SBN: 978-3-527-31825-4 3 VI I CONTENTS 2.4 2.4.1 2.4.2 2.4.3
2.4.4 2.4.5 2.4.6 2.4.7 2.4.8 2.4.9 2.4.10 2.4.11 2.4.12 2.4.13 2.5 3.1
3.2 3.2.1 3.2.2 3.2.3 3.3 3.3.1 3.3.1.1 3.3.1.2 3.3.1.3 3.3.1.4 3.3.2
3.3.2.1 3.3.2.2 3.3.2.3 3.3.2.4 3.3.2.5 3.3.2.6 3.3.2.7 3.3.2.8 3.4
EXAMPLES OF ENHANCING THE ENANTIOSELECTIVITY OF ENZYMES BY* DIRECTED
EVOLUTION 28* LIPASE FROM PSEUDOMONAS AERUGINOSA (PAL) 28* OTHER LIPASES
38* ESTERASES 38* HYDANTOINASES 39* NITRILASES 39* EPOXIDE HYDROLASES
41* PHOSPHOTRIESTERASES 45* AMINOTRANSFERASES 45* ALDOLASES 46*
CYCLOHEXANONE AND CYCLOPENTANONE MONOOXYGENASES AS* BAEYER-VILLIGERASES
AND SULFOXIDATION CATALYSTS 48* MONOAMINE OXIDASES 54* CYTOCHROME P450
ENZYMES 55* OTHER ENZYMES 55* CONCLUSIONS AND PERSPECTIVES 56*
REFERENCES 56* THE SEARCH FOR NEW ENZYMES 65* JEAN-LOUIS REYMOND AND
WOLFGANG STREIT* INTRODUCTION 65* MECHANISM-BASED ENZYME DESIGN THE
GENOMES OF NOT YET CULTURED MICROBES AS RESOURCES* 66* CATALYTIC
ANTIBODIES 66* RATIONAL DESIGN OF NEW CATALYSTS ON ENZYME AND PROTEIN
BASIS 69* SYNTHETIC ENZYME MODELS 71* METAGENOMICS 71* CONSTRUCTION OF
METAGENOME-DERIVED DNA LIBRARIES 72* SELECTION OF THE ENVIRONMENT 72*
CLONING STRATEGIES 73* SCREENING AND DETECTION TECHNOLOGIES 73* MAJOR
PROBLEMS THAT NEED TO BE ADDRESSED 74* FOR NOVEL GENES 75*
POLYSACCHARIDE DEGRADINGJMODIFYING ENZYMES 75* LIPOLYTIC BIOCATALYSTS
77* VITAMIN BIOSYNTHESIS 77* NITRILASES, NITRILE HYDRATASES, AND
AMIDASES 78* OXIDOREDUCTASESJDEHYDROGENASES 79* PROTEASES 79* GLYCEROL
HYDRATASES 79* ANTIBIOTICS AND PHARMACEUTICALS 79* CONCLUSION 80*
REFERENCES 80* CONTENTS I VII* 11* SYNTHETIC APPLICATIONS 87* 4* DYNAMIC
KINETIC RESOLUTIONS 89* BELEN MARTIN-MATUTE AND JAN-E. BAECKVALL 4.1*
INTRODUETION 89* 4.1.1* SYNTHESIS OF ENANTIOMERICALLY PURE COMPOUNDS 89*
4.1.2* KINETIC RESOLUTION (KR) AND DYNAMIC KINETIC* RESOLUTION (DKR) 90*
4.1.3* ENZYMES IN ORGANIC CHEMISTRY 91* 4.2* METAL-CATALYZED
RACEMIZATION 92* 4.2.1* DKR OF ALLYLIC ACETATES AND ALLYLIC ALCOHOLS 93*
4.2.2* DKR OF SEC-ALCOHOLS 94* 4.2.3* DKR OF AMINES 98* 4.3*
BASE-CATALYZED RACEMIZATION 98* 4.3.1* DKR OFTHIOESTERS 99* 4.3.2* DKR
OF ACTIVATED ESTERS LOO 4.3.3* DKR OF OXAZOLONES LOO 4.3.4* DKR OF
HYDANTOINS 101* 4.3.5* DKR OF ACYLOINS LOL 4.4* ACID*CATALYZED
RACEMIZATION LOL 4.5* RACEMIZATION THROUGH CONTINUOUS REVERSIBLE
FORMATION-CLEAVAGE OF THE SUBSTRATE LO2 4.5.1* DKR OF CYANOHYDRINS 103*
4.5.2* DKR OF HEMITHIOATHETALS LO3 4.6* RACEMIZATION CATALYZED BY
ALDEHYDES 104* 4.7* ENZYME-CATALYZED RACEMIZATION LO6 4.8* RACEMIZATION
THROUGH S N 2 DISPLACEMENT 106* 4.9* OTHER RACEMIZATION METHODS 107*
4.9.1* DKR OF 5-HYDROXY-2-(5H)-FURANONES 107* 4.9.2* DKR OF HEMIAMINALS
LO7 4.9.3* DKR OF 8-AMINO-5,6,7,8-TETRAHYDROQUINOLINE 108* 4.10*
CONCLUDING REMARKS LO9 REFERENCES 1LO 5* DERACEMIZATION AND
ENANTIOCONVERGENT PROCESSES 115* NICHOLASJ. TURNER 5.1* INTRODUCTION
115* 5.2* DERACEMIZATION PROCESSES 116* 5.2.1* CYCLIC
OXIDATION-REDUCTION SYSTEMS 116* 5.2.2* MICROBIAL DERACEMIZATION OF
SECONDARY ALCOHOLS USING A SINGLE* MICROORGANISM 122* 5.2.3*
DERACEMIZATION OF ALCOHOLS USING TWO ENZYMEJMICROORGANISM* SYSTEMS 124*
5.2.4* EPOXIDES 126* VIII I CONTENTS 5.2.5 5.3 5.3.1 5.3.2 5.4 6* 6.1
6.1.1 6.1.2 6.1.3 6.1.4 6.2 6.2.1 6.2.2 6.2.3 6.2.4 6.2.5 6.2.6 6.2.7
6.3 6.4 6.5 7* 7.1 7.2 7.3 7.4 7.4.1 7.4.2 7.4.3 7.4.4 7.5 7.6 7.7
CARBOXYLIC ACIDS 126* ENANTIOCONVERGENT PROCESSES 127* EPOXIDE
HYDROLYSIS 128* SULFATASES 129* CONCLUSIONS AND FUTURE PROSPECTS 130*
REFERENCES 130* TRANSESTERIFICATION AND HYDROLYSIS OF CARBOXYLIC* ACID
DERIVATIVES, ALCOHOLS, AND EPOXIDES 133* ROBERT CHENEVERT, PIERRE MORIN,
AND NICHOLAS PELCHAT LNTRODUCTION AND GENERAL ASPECTS 133* KINETIC
RESOLUTION, DYNAMIC KINETIC RESOLUTION, AND* ENANTIOSELECTIVE
BIOTRANSFORMATIONS OF CARBOXYLIC* SCOPE 133* REACTION CONDITIONS 133*
DESYMMETRIZATION 134* ENANTIOCONVERGENT TRANSFORMATION 137* ACID
DERIVATIVES 137* ESTER HYDROLYSIS 137* ESTER ALCOHOLYSIS 140*
ESTERIFICATION OF CARBOXYLIC ACIDS 140* LACTONES 142* ANHYDRIDES 143*
HYDROLYSIS OFNITRILES 144* HYDROLYSIS OF AMIDES, LACTAMS, AND HYDANTOINS
146* ENANTIOSELECTIVE ENZYMATIC TRANSFORMATIONS OF ALCOHOLS 150*
HYDROLYSIS OF EPOXIDES 157* CONCLUSION 162* REFERENCES 163* AMINOLYSIS
AND AMMONOLYSIS OFCARBOXYLIC ACID DERIVATIVES 171* VICENTE
GOTOR-FERNANDEZ AND VICENTE GOTOR INTRODUCTION 171* MECHANISM OF
ENZYMATIC AMMONOLYSIS AND AMINOLYSIS* REACTIONS 172* AMINOLYSIS AND
AMMONOLYSIS OF CARBOXYLIC ACIDS 174* AMINOLYSIS AND AMMONOLYSIS OF
ESTERS 176* PREPARATION OFNONCHIRAL AMIDES 176* RESOLUTION OF ESTERS
178* RESOLUTION OF AMINES, DIAMINES, AND AMINOALCOHOLS 180*
DESYMMETRIZATION OF DIESTERS 184* KINETIC RESOLUTION OF SECONDARY AMINES
185* TOWARD THE SYNTHESIS OF SS-AMINOACID DERIVATIVES 186* SUMMARY AND
OUTLOOK 188* REFERENCES 189* 8 8.1 8.2 8.2.1 8.2.2 8.2.3 8.2.4 8.2.5
8.2.6 8.3 8.3.1 8.3.2 8.3.2.1 8.3.2.2 8.3.2.3 8.3.2.4 8.3.3 8.3.4
8.3.4.1 8.3.4.2 8.3.4.3 8.4 8.4.1 8.4.1.1 8.4.1.2 8.4.2 8.4.3 8.4.4 8.5
8.5.1 8.5.2 8.5.3 8.5.3.1 8.5.3.2 8.6 9* 9.1 9.2 9.2.1 9.2.2 CONTENTS
IIX ENZYMATIC REDUCTION REACTION 193* KAORU NAKAMURA AND TOMOKO MATSUDA
INTRODUCTION 193* HYDROGEN SOURCE FOR COENZYME REGENERATION 193* ALCOHOL
AS A HYDROGEN SOURCE OFREDUCTION 194* SUGAR AS A HYDROGEN SOURCE OF
REDUCTION 194* FORMATE AS A HYDROGEN SOURCE OF REDUCTION 194* MOLECULAR
HYDROGEN AS A HYDROGEN SOURCE OF REDUCTION 195* LIGHT ENERGY AS A
HYDROGEN SOURCE OF REDUCTION 196* ELECTRIC POWER AS A HYDROGEN SOURCE OF
REDUCTION 198* METHODOLOGY FOR STEREOCHEMICAL CONTROL 199* SCREENING OF
MICROBES 199* MODIFICATION OF BIOCATALYSTS BY GENETIC METHODS 201*
MODIFIED YEAST 201* OVEREXPRESSION 202* COEXPRESSION OF GENES FOR
CARBONYJ REDUCTASE AND COFACTOR-REGENERATING ENZYMES 203* MODIFICATION
OF BIOCATALYSTS: DIRECTED EVOLUTION 204* MODIFICATION OF SUBSTRATES 205*
MODIFICATION OF REACTION CONDITIONS 206* ACETONE TREATMENT OF THE CELL
206* SELECTIVE INHIBITOR 207* REACTION TEMPERATURE 208* MEDIUM
ENGINEERING 209* ORGANIC SOLVENT 209* SOLUBLE ORGANIC SOLVENT 209*
AQUEOUS-ORGANIC TWO-PHASE REACTION 209* USE OF HYDROPHOBIC RESIN, XAD
211* SUPERCRITICAL CARBON DIOXIDE 213* IONIC LIQUID 215* SYNTHETIC
APPLICATIONS 216* REDUCTION OF ALDEHYDE 216* REDUCTION OF KETONE 216*
DYNAMIC KINETIC RESOLUTION AND DERACEMIZATION 221* DYNAMIC KINETIC
RESOLUTION 221* DERACEMIZATION THROUGH OXIDATION AND REDUCTION 223*
CONCLUSIONS 224* REFERENCES 225* BIOOXIDATIONS IN CHIRAL SYNTHESIS 229*
MARKO D. MIHOVILOVIC AND DARIO A. BIANCHI* INTRODUCTION 229* OXIDATIONS
OF AICOHOLS AND AMINES 231* REGIOSELECTIVE OXIDATION OF AICOHOLS 231*
DESYMMETRIZATIONS OF DIOLS 233* X I CONTENTS 9.2.3 9.2.4 9.2.5 9.3 9.3.1
9.3.2 9.3.3 9.4 9.5 9.5.1 9.5.2 9.5.3 9.5.4 9.6 9.6.1 9.6.2 9.6.3 9.7
9.7.1 9.7.2 9.8 9.9 10* 10.1 10.2 10.3 10.3.1 10.3.2 10.4 10.4.1 10.4.2
10.4.3 10.5 10.6. 10.7 10.8 KINETIC RESOLUTION OF PRIMARY AND SECONDARY
ALCOHOLS 234* DERACEMIZATION OF SECONDARY ALCOHOLS 235* DERACEMIZATION
OF AMINES 237* OXYGENATION OFNONACTIVATED CARBON CENTERS 237*
HYDROXYLATIONS BY WILD-TYPE WHOLE-CELLS 238* HYDROXYLATIONS BY
RECOMBINANT CYTOCHROME P450* MONOOXYGENASES 239* HYDROXYLATION VIA
HYDROPEROXIDE FORMATION 241* ENZYMATIC EPOXIDATION 241* BAEYER-VILLIGER
OXIDATIONS 243* CHEMOSELECTIVITY 245* DESYMMETRIZATIONS 246* KINETIC
RESOLUTIONS 248* REGIODIVERGENT BIOOXIDATIONS 251* HETEROATOM OXIDATIONS
253* SULFIDE OXIDATION 253* OXIDATION OF DITHIO-COMPOUNDS 256* OXIDATION
OF OTHER HETEROATOMS 256* ARYL DIHYDROXYLATIONS 257* DIOXYGENATION IN
ORTHO- AND META-POSITION 257* DIOXYGENATION IN IPSO- AND ORTHO-POSITION
262* HALOGENATION REACTIONS 263* SUMMARY AND OUTLOOK 265* REFERENCES
265* ALDOLASES: ENZYMES FOR MAKING AND BREAKING C-C BONDS 275*
WOLF-OIETER FESSNER INTRODUCTION 275* MECHANISTIC CLASSIFICATION 276*
PYRUVATE ALDOLASES 278* N-ACETYLNEURAMINIC ACID ALDOLASE 278* RELATED
PYRUVATE ALDOLASES 281* DIHYDROXYACETONE PHOSPHATE ALDOLASES 284*
FRUCTOSE 1,6-BISPHOSPHATE ALDOLASE 285* RELATED DHAP ALDOLASES 286*
PREPARATIVE APPLICATIONS 288* TRANSKETOLASE AND RELATED ENZYMES 302*
2-DEOXY-D-RIBOSE 5-PHOSPHATE ALDOLASE 305* GLYCINE ALDOLASES 308*
SUMMARY 311* REFERENCES 311* INDEX 319* |
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| id | DE-604.BV023020845 |
| illustrated | Illustrated |
| index_date | 2024-07-02T19:13:04Z |
| indexdate | 2024-07-20T09:27:43Z |
| institution | BVB |
| isbn | 9783527318254 3527318259 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-016224911 |
| oclc_num | 213380085 |
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| owner_facet | DE-703 DE-91G DE-BY-TUM DE-19 DE-BY-UBM DE-83 DE-11 |
| physical | XIV, 325 S. Ill., graph. Darst. 240 mm x 170 mm |
| publishDate | 2008 |
| publishDateSearch | 2008 |
| publishDateSort | 2008 |
| publisher | WILEY-VCH |
| record_format | marc |
| spelling | Asymmetric organic synthesis with enzymes ed. by Vicente Gotor ... Weinheim WILEY-VCH 2008 XIV, 325 S. Ill., graph. Darst. 240 mm x 170 mm txt rdacontent n rdamedia nc rdacarrier Asymmetric synthesis Enzymes Synthesis Organic compounds Synthesis Enzymkatalyse (DE-588)4152480-9 gnd rswk-swf Asymmetrische Synthese (DE-588)4135603-2 gnd rswk-swf Asymmetrische Synthese (DE-588)4135603-2 s Enzymkatalyse (DE-588)4152480-9 s DE-604 Gotor, Vicente Sonstige (DE-588)134010639 oth text/html http://deposit.dnb.de/cgi-bin/dokserv?id=2982596&prov=M&dok_var=1&dok_ext=htm Inhaltstext OEBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016224911&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Asymmetric organic synthesis with enzymes Asymmetric synthesis Enzymes Synthesis Organic compounds Synthesis Enzymkatalyse (DE-588)4152480-9 gnd Asymmetrische Synthese (DE-588)4135603-2 gnd |
| subject_GND | (DE-588)4152480-9 (DE-588)4135603-2 |
| title | Asymmetric organic synthesis with enzymes |
| title_auth | Asymmetric organic synthesis with enzymes |
| title_exact_search | Asymmetric organic synthesis with enzymes |
| title_exact_search_txtP | Asymmetric organic synthesis with enzymes |
| title_full | Asymmetric organic synthesis with enzymes ed. by Vicente Gotor ... |
| title_fullStr | Asymmetric organic synthesis with enzymes ed. by Vicente Gotor ... |
| title_full_unstemmed | Asymmetric organic synthesis with enzymes ed. by Vicente Gotor ... |
| title_short | Asymmetric organic synthesis with enzymes |
| title_sort | asymmetric organic synthesis with enzymes |
| topic | Asymmetric synthesis Enzymes Synthesis Organic compounds Synthesis Enzymkatalyse (DE-588)4152480-9 gnd Asymmetrische Synthese (DE-588)4135603-2 gnd |
| topic_facet | Asymmetric synthesis Enzymes Synthesis Organic compounds Synthesis Enzymkatalyse Asymmetrische Synthese |
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