Organic synthesis with enzymes in non-aqueous media:
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Sprache: | English |
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Wiley-VCH
2008
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Beschreibung: | XVII, 310 S. graph. Darst. |
ISBN: | 9783527318469 3527318461 |
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245 | 1 | 0 | |a Organic synthesis with enzymes in non-aqueous media |c ed. by Giacomo Carrea ... |
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300 | |a XVII, 310 S. |b graph. Darst. | ||
336 | |b txt |2 rdacontent | ||
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338 | |b nc |2 rdacarrier | ||
650 | 7 | |a Enzymen |2 gtt | |
650 | 7 | |a Synthese (chemie) |2 gtt | |
650 | 4 | |a Catalysis | |
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650 | 4 | |a Organic compounds |x Synthesis | |
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CONTENTS PREFACE XIII* LIST OF CONTRIBUTORS XV* PART ONE BIOCATALYSIS IN
NEAT ORGANIC SOLVENTS- FUNDAMENTALS FUNDAMENTALS OF BIOCATALYSIS IN NEAT
ORGANIC SOLVENTS 3* PATRICK ADLERCREUTZ 1.1 INTRADUCTION 3* 1.2 EFFECTS
OFWATER ON BIOCATALYTIC REACTIONS 3* 1.2.1 QUANTIFICATION OFWATER IN
LOW-WATER SYSTEMS 3* 1.2.2 WATER ACTIVITY CONTRAL 4* 1.2.2.1 WATER
ACTIVITY CONTRAL USING SATURATED SAH SOLUTIONS 4* 1.2.2.2 WATER ACTIVITY
CONTRAL USING SENSORS 5* 1.2.2.3 WATER ACTIVITY CONTRAL USING PAIRS OF
SAH HYDRATES 5* 1.2.3 DISTRIBUTION OF WATER 5* 1.2.3.1 HYSTERESIS
EFFECTS 8* 1.2.4 WATER EFFECTS ON ACTIVITY 8* 1.2.5 WATER EFFECTS ON
SELECTIVITY 10* 1.2.6 WATER EFFECTS ON STABILITY 12* 1.3 SOLVENT EFFECTS
13* 1.3.1 SOLVENT EFFECTS ON ENZYME ACTIVITY 13* 1.3.2 SOLVENT EFFECTS
ON STABILITY 16* 1.4 EFFECTS ON EQUILIBRIA 18* 1.4.1 WATER EFFECTS ON
EQUILIBRIA 19* 1.4.2 SOLVENT EFFECTS ON EQUILIBRIA 20* 1.5 EFFECTS OF PH
IN ORGANIC SOLVENTS 21* 1.6 CONCLUDING REMARKS 22* 2 EFFECTS OF ORGANIC
SOLVENTS ON ENZYME SELECTIVITY 25* JAAP A. JONGEJAN 2.1 INTRADUCTION 25*
2.2 ENZYME ENANTIOSELECTIVITY 26* 2.3 EFFECTS OF ORGANIC SOLVENTS ON THE
E-VALUE 27* ORGANIC SYNTHESIS WITH ENZYMES IN NON-AQUEOUS MEDIA. EDITED
BY GIACOMO CARREA AND SERGIO RIVA COPYRIGHT 2008 WILEY-VCH VERLAG GMBH
& CO. KGAA, WEINHEIM ISBN: 978-3-527-31846-9 VI I CONTENTS 2.4 2.5 2.6
2.7 2.8 2.9 3* 3.1 3.2 3.2.1 3.2.2 3.2.3 3.2.4 3.3 3.3.1 3.3.2 3.3.3
3.3.4 3.3.4.1 3.3.4.2 3.4 3.4.1 3.4.2 3.4.3 3.5 4* 4.1 4.1.1 4.1.2 4.1.3
4.1.4 4.2 4.2.1 4.2.1.1 4.2.1.2 4.2.1.3 4.2.1.4 POSSIBLE CAUSES OF THE
COMPLEXITY OF SOLVENT EFFECTS ON E 30* THE ACCURACY OF E-VALUE
DETERMINATIONS 31* KINETIC AND THERMODYNAMIC ANALYSIS OF THE SPECIFICITY
CONSTANTS 33* SOLVENTS EFFECTS ON NON-HYDROLYTIC ENZYMES 36* MAJOR
ACHIEVEMENTS 38* CONCLUDING REMARKS 41* ACTIVATING ENZYMES FOR USE IN
ORGANIC SOLVENTS 47* ANNE L. SERDAKOWSKI, JONATHAN S. DORDICK
INTRODUCTION 47* ENZYMES DO FUNCTION WITHOUT WATER AS A BULK SOLVENT-
LESSONS FROM* SAH ACTIVATION IS NOT DUE TO ARELAXATION OF DIFFUSIONAL*
WATER-A UNIQUE AND NECESSARY SOLVENT FOR ENZYMATIC CATALYSIS 49*
CHALLENGES FOR ENZYMATIC CATALYSIS IN WATER 49* EXTREME HALOPHILES 49*
BEHAVIOR OF ENZYMES IN THE ABSENCE OF BULK WATER 50* REMOVING WATER FROM
ENZYMES-THE EFFECT OF LYOPHILIZATION ON* ENZYME STRUCTURE AND FUNCTION
51* ENZYME ACTIVATION IN NONAQUEOUS MEDIA 53* ADDITION OFWATER AND WATER
MIMICS 53* IMMOBILIZATION 55* SOLID-STATE BUFFERS 58* LYOPHILIZATION IN
THE PRESENCE OF EXCIPIENTS 59* POLYMERS 60* CROWN ETHERS AND
CYCLODEXTRINS 60* SAH-ACTIVATED ENZYMES 61* LIMITATIONS 63* MECHANISM OF
SAH ACTIVATION 63* THE STRUCTURAL AND MOLECULAR DYNAMICS OF SAH
ACTIVATION 66* CONCLUSIONS 67* PART TWO BIOCATALYSIS IN NEAT ORGANIC
SOLVENTS-SYNTHETIC APPLICATIONS EXPLOITING ENANTIOSELECTIVITY OF
HYDROLASES IN ORGANIC SOLVENTS 75* HANS-ERIK HOEGBERG INTRODUCTION 75*
ENANTIOSELECTIVITY 75* DESYMMETRIZATION 78* THE REVERSIBILITY PROBLEM
79* DETERMINING AND OPTIMIZING ENANTIOSELECTIVITY 81* ENANTIOSELECTIVE
REACTIONS IN ORGANIC SOLVENTS 82* REACTIONS OF ALCOHOLS 82* PRIMARY
ALCOHOLS 82* SECONDARY ALCOHOLS 88* TERTIARY ALCOHOLS 100* RESOLUTION OF
DIHYDROXYBIARYLS 100* CONTENTS I VII* 4.2.2 4.2.2.1 4.2.2.2 4.2.2.3
4.2.3 4.2.3.1 4.2.3.2 4.3 5* 5.1 5.1.1 5.1.2 5.1.3 5.2 5.2.1 5.2.1.1
5.2.1.2 5.2.1.3 5.2.1.4 5.2.1.5 5.2.2 5.2.3 5.2.3.1 5.2.3.2 5.2.4 5.2.5
5.2.6 5.2.7 5.2.8 5.2.8.1 5.2.8.2 5.2.8.3 5.2.9 5.2.9.1 5.2.9.2 5.2.9.3
5.3 5.3.1 5.3.1.1 5.3.1.2 5.3.1.3 5.3.2 5.4 REACTION OF AMINES 101*
ALKYLAMINES 101* ARYLALKYLAMINES 101* AMINO ACID DERIVATIVES 104*
REACTION OF ACID DERIVATIVES 104* ACIDS 104* OTHER ACID DERIVATIVES 107*
SUMMARY AND OUTLOOK 108* CHEMOENZYMATIC DERACEMIZATION PROCESSES 113*
BETEN MARTFN-MATUTE AND JAN-E. BAECKVALL INTRODUCTION 113* ASYMMETRIE
SYNTHESIS METHODS 113* DYNAMIC KINETIC RESOLUTION (DKR) 115* CYCLIC
DERACEMIZATIONS 116* DYNAMIC KINETIC RESOLUTION 117* BASE-CATALYZED
RACEMIZATION 117* DKR OFTHIOESTERS 118* DKR OF ACTIVATED ESTERS 118* DKR
OF OXAZOLONES 118* DKR OF HYDANTOINS 119* DKR OF ACYLOINS 119*
ACID-CATALYZED RACEMIZATION 119* RACEMIZATION THROUGH CONTINUOUS
REVERSIBLE FORMATION-CLEAVAGE OF* THE SUBSTRATE 120* DKR OF CYANOHYDRINS
121* DKR OF HEMITHIOACETALS 122* RACEMIZATION CATALYZED BY ALDEHYDES
122* ENZYME-CATALYZED RACEMIZATION 124* RACEMIZATION THROUGH S N 2
DISPLACEMENT 125* RADICAL RACEMIZATION 125* METAL-CATALYZED RACEMIZATION
126* DKR OF ALLYLIC ACETATES AND ALLYLIC ALCOHOLS 127* DKR OF
SEC-ALCOHOLS 128* DKR OF AMINES 132* OTHER RACEMIZATION METHODS 133* DKR
OF 5-HYDROXY-2-(5H)-FURANONES 133* DKR OF HEMIAMINALS 133* DKR OF
8-AMINO-5,6,7,8-TETRAHYDROQUINOLINE 134* CYC1IC DERACEMIZATIONS 135*
CHEMOENZYMATIC CYCLIC DERACEMIZATIONS 136* CYCLIC DERACEMIZATIONS OF
AMINO ACIDS 136* CHEMOENZYMATIC CYCLIC DERACEMIZATIONS OF HYDROXY ACIDS
137* CHEMOENZYMATIC CYC1IC DERACEMIZATIONS OF AMINES 138* BIOCATALYZED
DERACEMIZATIONS 139* CONCLUDING REMARKS 140* VIII I CONTENTS 6* 6.1 6.2
6.3 6.3.1 6.3.2 6.3.3 6.3.3.1 6.3.3.2 6.3.3.3 6.3.3.4 6.3.4 6.3.5 6.4 7*
7.1 7.2 7.3 7.3.1 7.3.2 7.3.3 7.3.4 7.3.5 7.4 7.4.1 7.4.2 7.5 7.6 7.6.1
7.7 7.7.1 7.8 7.8.1 7.8.2 7.9 EXPLOITING ENZYME CHEMOSELECTIVITY AND
REGIOSELECTIVITY 145* SERGIO RIVA INTRODUETION 145* CHEMOSELEETIVITY OF
HYDROLASES 146* REGIOSELEETIVITY OF HYDROLASES 148* REGIOSELEETIVE
AEYLATION OF POLYOLS 148* REGIOSELEETIVE AEYLATION OF CARBOHYDRATES 150*
REGIOSELEETIVE AEYLATION OF NATURAL GLYEOSIDES 153* TERPENE GLYEOSIDES
154* FLAVONOID GLYEOSIDES 155* NUCLEOSIDES 156* OTHER GLYEOSIDES 158*
REGIOSELEETIVE ALCOHOLYSES 158* RATIONALES 160* CLOSING REMARKS 162*
INDUSTRIAL-SCALE APPLICATIONS OF ENZYMES IN NON-AQUEOUS SOLVENTS 169*
DAVID POLLARD AND BIRGIT KOSJEK INTRODUETION 169* THE SYNTHESIS OF
S-N(TERT-BUTOXYEARBONYL)-3-HYDROXYMETHYLPIPERIDINE* SYNTHESIS OF
DESOXYSPERGUALIN (IMMUNOSUPPRESSANT AND ANTITUMOR* ESTER RESOLUTION FAR
THE SYNTHESIS OF EMTRIEITABINE (ANTIVIRAL* REGIOSELEETIVE AEYLATION OF
DRUG INTERMEDIATE FOR AN ANTILEUKAEMIE* ESTER SYNTHESIS BY
ESTERIFIEATION 170* RESOLUTION OF RAEEMIE ALCOHOLS 170* SYNTHESIS OF A
CHIRAL R-(+) HYDROMETHYL GLUTARYL COENZYME A* REDUETASE INHIBITOR
(ANTIEHOLESTEROL DRUG) 171* (TRYPTASE INHIBITOR) 172* THE SYNTHESIS OF
(S)-[I-(AEETOXYL)-4-(3-PHENYL) BUTYL]PHOSPHONIC ACID* DIETHYL ESTER
(ANTIEHOLESTEROL DRUG) 172* DRUG) 173* DYNAMIE KINETIE RESOLUTION OF
RAEEMIE ALCOHOLS 174* KINETIE RESOLUTION OF RAEEMIE AMINES 174*
RESOLUTION OF RAE-2- BUTYLAMINE 175* SYNTHESIS OF A SELEETIVE,
NON-PEPTIDE, NON-SULFHYDRYL FAMESYL PROTEIN* TRANSFER INHIBITOR
(ANTITUMOR AGENT) 177* RESOLUTION OF AMINO ALCOHOLS AND METHYL ETHERS
178* RESOLUTION OF AN ESTER 178* DRUG) 178* DESYMMETRIZATION BY
TRANSESTERIFIEATION 179* SYNTHESIS OF AN ANTIFUNGAL AZOLE DERIVATIVE
179* REGIOSELEETIVE AEYLATION 180* AGENT 180* REGIOSELEETIVE AEYLATION
OF RIBAVIRIN: ANTIVIRAL AGENT 180* ASYMMETRIE RING OPENING OF RAEEMIE
AZLAETONE 181* CONTENTS* IIX* 7.9.1* SYNTHESIS OF
(S)-BENZYL-L-TERT-LEUCINE BUTYL ESTER 181* 7.9.2* SYNTHESIS OF
(S)-Y-FLUOROLEUCINE ETHYL ESTER 182* 7.10* CYANOHYDRIN FORMATION 183*
7.10.1* SYNTHESIS OF (R)-2-CHLOROMANDELIC ACID: INTERMEDIATE FOR*
CLOPIDOGREL 183* 7.10.2* SYNTHESIS OF CHIRAL PHENOXYBENZALDEHYDE
CYANOHYDRIN: INTERMEDIATE* FOR THE SYNTHESIS OF PYRETHROID INSECTICIDES
184* 7.10.3* HYDROCYANATION OF 3-PYRIDINECARBOXYALDEHYDE 185* 7.11*
OUTLOOK 186* PART THREE BIOCATALYSIS IN BIPHASIC AND NEW REACTION MEDIA
8* BIOCATALYSIS IN BIPHASIC SYSTEMS: GENERAL 191* PEDRO FERNANDES AND
JOAQUIM M. S. CABRAL 8.1* INTRODUCTION 191* 8.2* ORGANIC-AQUEOUS
BIPHASIC SYSTEMS: GENERAL CONSIDERATIONS 191* 8.3* CLASSIFICATION OF THE
SYSTEMS: MACRO- AND MICROHETEROGENEOUS* SYSTEMS 193* 8.4* MECHANISMS OF
ENZYME INACTIVATION 194* 8.5* APPROACHES TO PROTECTION OF THE ENZYME
195* 8.6* SOLVENT SELECTION 196* 8.7* OPERATIONAL PARAMETERS 198* 8.7.1*
INTERFACIAL AREA AND VOLUME PHASE RATIO 198* 8.7.2* MASS TRANSFER
COEFFICIENTS AND PROCESS MODELING 200* 8.8* REACTOR TYPES 205* 8.9*
DOWNSTREAM PROCESSING 206* 8.10* RECENT APPLICATIONS 207* 8.11*
CONCLUSIONS 207* ACKNOWLEDGMENTS 207* 9* BIOCATALYSIS IN BIPHASIC
SYSTEMS: OXYNITRILASES 211* MANUELA AVI AND HERFRIED GRIENGL 9.1*
INTRODUCTION 211* 9.2* BIPHASIC SYSTEMS 212* 9.2.1* LIQUID/LIQUID
BIPHASIC SYSTEMS 212* 9.2.1.1* BUFFER/ORGANIC SOLVENT 212* 9.2.1.2*
BUFFER/IONIC LIQUIDS 215* 9.2.2* LIQUID/SOLID BIPHASIC SYSTEMS 216*
9.2.2.1* CMDE ENZYME PREPARATIONS 216* 9.2.2.2* INERT CARRIERS 217*
9.2.2.3* CROSS-LINKING OF OXYNITRILASES 219* 9.2.3* OTHER BIPHASIC
SYSTEMS 220* 9.2.3.1* ENCAPSULATION IN SOL-GEL MATRICES 222* 9.2.3.2*
COMPARISON OF CLEAS AND SOL-GEL HNLS 223* 9.3* CONCLUSION 223* 10 11 X I
CONTENTS 10.1 10.2 10.3 10.4 10.5 10.6 10.7 10.7.1 10.7.2 10.7.3 10.7.4
10.8 10.9 11.1 11.2 11.2.1 11.2.1.1 11.2.1.2 11.3 11.3.1 11.3.2 11.3.3
11.3.4 11.3.4.1 11.4 12* 12.1 12.2 12.3 12.4 LONIC LIQUIDS AS MEDIA FOR
ENZYMATIC TRANSFORMATIONS 227* ROGER A. SHELDON AND FRED VAN RANTWIJK
INTRODUCTION 227* SOLVENT PROPERTIES OF LONK LIQUIDS 228* ENZYMES IN
LONK LIQUIDS 230* ENZYMES IN NEARLY ANHYDROUS LONIC LIQUIDS 231*
STABILITY OF ENZYMES IN NEARLY ANHYDROUS LONIC LIQUIDS 235* WHOLE-CELL
BIOTRANSFORMATIONS IN LONIC LIQUIDS 236* BIOTRANSFORMATIONS IN LONIC
LIQUID MEDIA 237* LIPASES AND PROTEASES 237* DYNAMIC KINETIC RESOLUTION
OF CHIRAL ALCOHOLS 243* GLYCOSIDASES 244* OXIDOREDUCTASES 245*
DOWNSTREAM PROCESSING 247* CONCLUSIONS 248* SOLID/GAS BIOCATALYSIS 255*
ISABELLE GOUBET, MARIANNE GRABER, SYLVAIN LAMARE, THIERRY MAUGARD AND
MARIE-DOMINIQUE LEGOY INTRODUCTION 255* OPERATING SOLID/GAS SYSTEMS 258*
EXAMPLES OF THE USE OF SOLID/GAS SYSTEMS 263* EXAMPLE 1: SYNTHESIS OF
CHIRAL COMPOUNDS USING ENZYMES IN SOLID/* GAS REACTORS 263* EXAMPLE 2:
CONVERSION OF GASEOUS HALOGENATED COMPOUNDS BY* DEHYDRATED BACTERIA 267*
INFLUENCE OF OPERATIONAL PARAMETERS ON THE DEHALOGENASE ACTIVITY OF*
WHOLE DEHYDRATED CELLS 269* EFFECT OFTEMPERATURE 269* EFFECT OF WATER
ACTIVITY 269* EFFECT OF BUFFER PH BEFORE DEHYDRATION 271* RANGE OF
SUBSTRATES 271* EXAMPLE 3: SCALING UP THE SYSTEM; APPLICATION TO
INDUSTRIAL* PRODUCTION 272* CONCLUSION 274* BIOCATALYSIS WITH
UNDISSOLVED SOLID SUBSTRATES AND PRODUCTS 279* ALESSANDRA BASSO, SARA
CANTONE, CYNTHIA EBERT, PETER J. HALLING AND LUCIA GARDOSSI INTRODUCTION
279* THE REACTION SYSTEM: CLASSIFICATION 280* THEORY 280* FACTORS
AFFECTING THE REACTIONS IN THE PRESENCE OF UNDISSOLVED*
SUBSTRATES/PRODUCTS 284* PRECIPITATION-DRIVEN SYNTHESIS OF PEPTIDES 287*
12.5 CONTENTS* IXI 12.6* PRECIPITATION-DRIVEN SYNTHESIS OF ESTERS AND
SURFACTANTS 292 12.7* THE SYNTHESIS OF SS-LACTAM ANTIBIOTICS IN THE
PRESENCE OF UNDISSOLVED SUBSTRATES 294 12.8* CONCLUSION 298 INDEX 303 |
adam_txt |
CONTENTS PREFACE XIII* LIST OF CONTRIBUTORS XV* PART ONE BIOCATALYSIS IN
NEAT ORGANIC SOLVENTS- FUNDAMENTALS FUNDAMENTALS OF BIOCATALYSIS IN NEAT
ORGANIC SOLVENTS 3* PATRICK ADLERCREUTZ 1.1 INTRADUCTION 3* 1.2 EFFECTS
OFWATER ON BIOCATALYTIC REACTIONS 3* 1.2.1 QUANTIFICATION OFWATER IN
LOW-WATER SYSTEMS 3* 1.2.2 WATER ACTIVITY CONTRAL 4* 1.2.2.1 WATER
ACTIVITY CONTRAL USING SATURATED SAH SOLUTIONS 4* 1.2.2.2 WATER ACTIVITY
CONTRAL USING SENSORS 5* 1.2.2.3 WATER ACTIVITY CONTRAL USING PAIRS OF
SAH HYDRATES 5* 1.2.3 DISTRIBUTION OF WATER 5* 1.2.3.1 HYSTERESIS
EFFECTS 8* 1.2.4 WATER EFFECTS ON ACTIVITY 8* 1.2.5 WATER EFFECTS ON
SELECTIVITY 10* 1.2.6 WATER EFFECTS ON STABILITY 12* 1.3 SOLVENT EFFECTS
13* 1.3.1 SOLVENT EFFECTS ON ENZYME ACTIVITY 13* 1.3.2 SOLVENT EFFECTS
ON STABILITY 16* 1.4 EFFECTS ON EQUILIBRIA 18* 1.4.1 WATER EFFECTS ON
EQUILIBRIA 19* 1.4.2 SOLVENT EFFECTS ON EQUILIBRIA 20* 1.5 EFFECTS OF PH
IN ORGANIC SOLVENTS 21* 1.6 CONCLUDING REMARKS 22* 2 EFFECTS OF ORGANIC
SOLVENTS ON ENZYME SELECTIVITY 25* JAAP A. JONGEJAN 2.1 INTRADUCTION 25*
2.2 ENZYME ENANTIOSELECTIVITY 26* 2.3 EFFECTS OF ORGANIC SOLVENTS ON THE
E-VALUE 27* ORGANIC SYNTHESIS WITH ENZYMES IN NON-AQUEOUS MEDIA. EDITED
BY GIACOMO CARREA AND SERGIO RIVA COPYRIGHT 2008 WILEY-VCH VERLAG GMBH
& CO. KGAA, WEINHEIM ISBN: 978-3-527-31846-9 VI I CONTENTS 2.4 2.5 2.6
2.7 2.8 2.9 3* 3.1 3.2 3.2.1 3.2.2 3.2.3 3.2.4 3.3 3.3.1 3.3.2 3.3.3
3.3.4 3.3.4.1 3.3.4.2 3.4 3.4.1 3.4.2 3.4.3 3.5 4* 4.1 4.1.1 4.1.2 4.1.3
4.1.4 4.2 4.2.1 4.2.1.1 4.2.1.2 4.2.1.3 4.2.1.4 POSSIBLE CAUSES OF THE
COMPLEXITY OF SOLVENT EFFECTS ON E 30* THE ACCURACY OF E-VALUE
DETERMINATIONS 31* KINETIC AND THERMODYNAMIC ANALYSIS OF THE SPECIFICITY
CONSTANTS 33* SOLVENTS EFFECTS ON NON-HYDROLYTIC ENZYMES 36* MAJOR
ACHIEVEMENTS 38* CONCLUDING REMARKS 41* ACTIVATING ENZYMES FOR USE IN
ORGANIC SOLVENTS 47* ANNE L. SERDAKOWSKI, JONATHAN S. DORDICK
INTRODUCTION 47* ENZYMES DO FUNCTION WITHOUT WATER AS A BULK SOLVENT-
LESSONS FROM* SAH ACTIVATION IS NOT DUE TO ARELAXATION OF DIFFUSIONAL*
WATER-A UNIQUE AND NECESSARY SOLVENT FOR ENZYMATIC CATALYSIS 49*
CHALLENGES FOR ENZYMATIC CATALYSIS IN WATER 49* EXTREME HALOPHILES 49*
BEHAVIOR OF ENZYMES IN THE ABSENCE OF BULK WATER 50* REMOVING WATER FROM
ENZYMES-THE EFFECT OF LYOPHILIZATION ON* ENZYME STRUCTURE AND FUNCTION
51* ENZYME ACTIVATION IN NONAQUEOUS MEDIA 53* ADDITION OFWATER AND WATER
MIMICS 53* IMMOBILIZATION 55* SOLID-STATE BUFFERS 58* LYOPHILIZATION IN
THE PRESENCE OF EXCIPIENTS 59* POLYMERS 60* CROWN ETHERS AND
CYCLODEXTRINS 60* SAH-ACTIVATED ENZYMES 61* LIMITATIONS 63* MECHANISM OF
SAH ACTIVATION 63* THE STRUCTURAL AND MOLECULAR DYNAMICS OF SAH
ACTIVATION 66* CONCLUSIONS 67* PART TWO BIOCATALYSIS IN NEAT ORGANIC
SOLVENTS-SYNTHETIC APPLICATIONS EXPLOITING ENANTIOSELECTIVITY OF
HYDROLASES IN ORGANIC SOLVENTS 75* HANS-ERIK HOEGBERG INTRODUCTION 75*
ENANTIOSELECTIVITY 75* DESYMMETRIZATION 78* THE REVERSIBILITY PROBLEM
79* DETERMINING AND OPTIMIZING ENANTIOSELECTIVITY 81* ENANTIOSELECTIVE
REACTIONS IN ORGANIC SOLVENTS 82* REACTIONS OF ALCOHOLS 82* PRIMARY
ALCOHOLS 82* SECONDARY ALCOHOLS 88* TERTIARY ALCOHOLS 100* RESOLUTION OF
DIHYDROXYBIARYLS 100* CONTENTS I VII* 4.2.2 4.2.2.1 4.2.2.2 4.2.2.3
4.2.3 4.2.3.1 4.2.3.2 4.3 5* 5.1 5.1.1 5.1.2 5.1.3 5.2 5.2.1 5.2.1.1
5.2.1.2 5.2.1.3 5.2.1.4 5.2.1.5 5.2.2 5.2.3 5.2.3.1 5.2.3.2 5.2.4 5.2.5
5.2.6 5.2.7 5.2.8 5.2.8.1 5.2.8.2 5.2.8.3 5.2.9 5.2.9.1 5.2.9.2 5.2.9.3
5.3 5.3.1 5.3.1.1 5.3.1.2 5.3.1.3 5.3.2 5.4 REACTION OF AMINES 101*
ALKYLAMINES 101* ARYLALKYLAMINES 101* AMINO ACID DERIVATIVES 104*
REACTION OF ACID DERIVATIVES 104* ACIDS 104* OTHER ACID DERIVATIVES 107*
SUMMARY AND OUTLOOK 108* CHEMOENZYMATIC DERACEMIZATION PROCESSES 113*
BETEN MARTFN-MATUTE AND JAN-E. BAECKVALL INTRODUCTION 113* ASYMMETRIE
SYNTHESIS METHODS 113* DYNAMIC KINETIC RESOLUTION (DKR) 115* CYCLIC
DERACEMIZATIONS 116* DYNAMIC KINETIC RESOLUTION 117* BASE-CATALYZED
RACEMIZATION 117* DKR OFTHIOESTERS 118* DKR OF ACTIVATED ESTERS 118* DKR
OF OXAZOLONES 118* DKR OF HYDANTOINS 119* DKR OF ACYLOINS 119*
ACID-CATALYZED RACEMIZATION 119* RACEMIZATION THROUGH CONTINUOUS
REVERSIBLE FORMATION-CLEAVAGE OF* THE SUBSTRATE 120* DKR OF CYANOHYDRINS
121* DKR OF HEMITHIOACETALS 122* RACEMIZATION CATALYZED BY ALDEHYDES
122* ENZYME-CATALYZED RACEMIZATION 124* RACEMIZATION THROUGH S N 2
DISPLACEMENT 125* RADICAL RACEMIZATION 125* METAL-CATALYZED RACEMIZATION
126* DKR OF ALLYLIC ACETATES AND ALLYLIC ALCOHOLS 127* DKR OF
SEC-ALCOHOLS 128* DKR OF AMINES 132* OTHER RACEMIZATION METHODS 133* DKR
OF 5-HYDROXY-2-(5H)-FURANONES 133* DKR OF HEMIAMINALS 133* DKR OF
8-AMINO-5,6,7,8-TETRAHYDROQUINOLINE 134* CYC1IC DERACEMIZATIONS 135*
CHEMOENZYMATIC CYCLIC DERACEMIZATIONS 136* CYCLIC DERACEMIZATIONS OF
AMINO ACIDS 136* CHEMOENZYMATIC CYCLIC DERACEMIZATIONS OF HYDROXY ACIDS
137* CHEMOENZYMATIC CYC1IC DERACEMIZATIONS OF AMINES 138* BIOCATALYZED
DERACEMIZATIONS 139* CONCLUDING REMARKS 140* VIII I CONTENTS 6* 6.1 6.2
6.3 6.3.1 6.3.2 6.3.3 6.3.3.1 6.3.3.2 6.3.3.3 6.3.3.4 6.3.4 6.3.5 6.4 7*
7.1 7.2 7.3 7.3.1 7.3.2 7.3.3 7.3.4 7.3.5 7.4 7.4.1 7.4.2 7.5 7.6 7.6.1
7.7 7.7.1 7.8 7.8.1 7.8.2 7.9 EXPLOITING ENZYME CHEMOSELECTIVITY AND
REGIOSELECTIVITY 145* SERGIO RIVA INTRODUETION 145* CHEMOSELEETIVITY OF
HYDROLASES 146* REGIOSELEETIVITY OF HYDROLASES 148* REGIOSELEETIVE
AEYLATION OF POLYOLS 148* REGIOSELEETIVE AEYLATION OF CARBOHYDRATES 150*
REGIOSELEETIVE AEYLATION OF NATURAL GLYEOSIDES 153* TERPENE GLYEOSIDES
154* FLAVONOID GLYEOSIDES 155* NUCLEOSIDES 156* OTHER GLYEOSIDES 158*
REGIOSELEETIVE ALCOHOLYSES 158* RATIONALES 160* CLOSING REMARKS 162*
INDUSTRIAL-SCALE APPLICATIONS OF ENZYMES IN NON-AQUEOUS SOLVENTS 169*
DAVID POLLARD AND BIRGIT KOSJEK INTRODUETION 169* THE SYNTHESIS OF
S-N(TERT-BUTOXYEARBONYL)-3-HYDROXYMETHYLPIPERIDINE* SYNTHESIS OF
DESOXYSPERGUALIN (IMMUNOSUPPRESSANT AND ANTITUMOR* ESTER RESOLUTION FAR
THE SYNTHESIS OF EMTRIEITABINE (ANTIVIRAL* REGIOSELEETIVE AEYLATION OF
DRUG INTERMEDIATE FOR AN ANTILEUKAEMIE* ESTER SYNTHESIS BY
ESTERIFIEATION 170* RESOLUTION OF RAEEMIE ALCOHOLS 170* SYNTHESIS OF A
CHIRAL R-(+) HYDROMETHYL GLUTARYL COENZYME A* REDUETASE INHIBITOR
(ANTIEHOLESTEROL DRUG) 171* (TRYPTASE INHIBITOR) 172* THE SYNTHESIS OF
(S)-[I-(AEETOXYL)-4-(3-PHENYL) BUTYL]PHOSPHONIC ACID* DIETHYL ESTER
(ANTIEHOLESTEROL DRUG) 172* DRUG) 173* DYNAMIE KINETIE RESOLUTION OF
RAEEMIE ALCOHOLS 174* KINETIE RESOLUTION OF RAEEMIE AMINES 174*
RESOLUTION OF RAE-2- BUTYLAMINE 175* SYNTHESIS OF A SELEETIVE,
NON-PEPTIDE, NON-SULFHYDRYL FAMESYL PROTEIN* TRANSFER INHIBITOR
(ANTITUMOR AGENT) 177* RESOLUTION OF AMINO ALCOHOLS AND METHYL ETHERS
178* RESOLUTION OF AN ESTER 178* DRUG) 178* DESYMMETRIZATION BY
TRANSESTERIFIEATION 179* SYNTHESIS OF AN ANTIFUNGAL AZOLE DERIVATIVE
179* REGIOSELEETIVE AEYLATION 180* AGENT 180* REGIOSELEETIVE AEYLATION
OF RIBAVIRIN: ANTIVIRAL AGENT 180* ASYMMETRIE RING OPENING OF RAEEMIE
AZLAETONE 181* CONTENTS* IIX* 7.9.1* SYNTHESIS OF
(S)-BENZYL-L-TERT-LEUCINE BUTYL ESTER 181* 7.9.2* SYNTHESIS OF
(S)-Y-FLUOROLEUCINE ETHYL ESTER 182* 7.10* CYANOHYDRIN FORMATION 183*
7.10.1* SYNTHESIS OF (R)-2-CHLOROMANDELIC ACID: INTERMEDIATE FOR*
CLOPIDOGREL 183* 7.10.2* SYNTHESIS OF CHIRAL PHENOXYBENZALDEHYDE
CYANOHYDRIN: INTERMEDIATE* FOR THE SYNTHESIS OF PYRETHROID INSECTICIDES
184* 7.10.3* HYDROCYANATION OF 3-PYRIDINECARBOXYALDEHYDE 185* 7.11*
OUTLOOK 186* PART THREE BIOCATALYSIS IN BIPHASIC AND NEW REACTION MEDIA
8* BIOCATALYSIS IN BIPHASIC SYSTEMS: GENERAL 191* PEDRO FERNANDES AND
JOAQUIM M. S. CABRAL 8.1* INTRODUCTION 191* 8.2* ORGANIC-AQUEOUS
BIPHASIC SYSTEMS: GENERAL CONSIDERATIONS 191* 8.3* CLASSIFICATION OF THE
SYSTEMS: MACRO- AND MICROHETEROGENEOUS* SYSTEMS 193* 8.4* MECHANISMS OF
ENZYME INACTIVATION 194* 8.5* APPROACHES TO PROTECTION OF THE ENZYME
195* 8.6* SOLVENT SELECTION 196* 8.7* OPERATIONAL PARAMETERS 198* 8.7.1*
INTERFACIAL AREA AND VOLUME PHASE RATIO 198* 8.7.2* MASS TRANSFER
COEFFICIENTS AND PROCESS MODELING 200* 8.8* REACTOR TYPES 205* 8.9*
DOWNSTREAM PROCESSING 206* 8.10* RECENT APPLICATIONS 207* 8.11*
CONCLUSIONS 207* ACKNOWLEDGMENTS 207* 9* BIOCATALYSIS IN BIPHASIC
SYSTEMS: OXYNITRILASES 211* MANUELA AVI AND HERFRIED GRIENGL 9.1*
INTRODUCTION 211* 9.2* BIPHASIC SYSTEMS 212* 9.2.1* LIQUID/LIQUID
BIPHASIC SYSTEMS 212* 9.2.1.1* BUFFER/ORGANIC SOLVENT 212* 9.2.1.2*
BUFFER/IONIC LIQUIDS 215* 9.2.2* LIQUID/SOLID BIPHASIC SYSTEMS 216*
9.2.2.1* CMDE ENZYME PREPARATIONS 216* 9.2.2.2* INERT CARRIERS 217*
9.2.2.3* CROSS-LINKING OF OXYNITRILASES 219* 9.2.3* OTHER BIPHASIC
SYSTEMS 220* 9.2.3.1* ENCAPSULATION IN SOL-GEL MATRICES 222* 9.2.3.2*
COMPARISON OF CLEAS AND SOL-GEL HNLS 223* 9.3* CONCLUSION 223* 10 11 X I
CONTENTS 10.1 10.2 10.3 10.4 10.5 10.6 10.7 10.7.1 10.7.2 10.7.3 10.7.4
10.8 10.9 11.1 11.2 11.2.1 11.2.1.1 11.2.1.2 11.3 11.3.1 11.3.2 11.3.3
11.3.4 11.3.4.1 11.4 12* 12.1 12.2 12.3 12.4 LONIC LIQUIDS AS MEDIA FOR
ENZYMATIC TRANSFORMATIONS 227* ROGER A. SHELDON AND FRED VAN RANTWIJK
INTRODUCTION 227* SOLVENT PROPERTIES OF LONK LIQUIDS 228* ENZYMES IN
LONK LIQUIDS 230* ENZYMES IN NEARLY ANHYDROUS LONIC LIQUIDS 231*
STABILITY OF ENZYMES IN NEARLY ANHYDROUS LONIC LIQUIDS 235* WHOLE-CELL
BIOTRANSFORMATIONS IN LONIC LIQUIDS 236* BIOTRANSFORMATIONS IN LONIC
LIQUID MEDIA 237* LIPASES AND PROTEASES 237* DYNAMIC KINETIC RESOLUTION
OF CHIRAL ALCOHOLS 243* GLYCOSIDASES 244* OXIDOREDUCTASES 245*
DOWNSTREAM PROCESSING 247* CONCLUSIONS 248* SOLID/GAS BIOCATALYSIS 255*
ISABELLE GOUBET, MARIANNE GRABER, SYLVAIN LAMARE, THIERRY MAUGARD AND
MARIE-DOMINIQUE LEGOY INTRODUCTION 255* OPERATING SOLID/GAS SYSTEMS 258*
EXAMPLES OF THE USE OF SOLID/GAS SYSTEMS 263* EXAMPLE 1: SYNTHESIS OF
CHIRAL COMPOUNDS USING ENZYMES IN SOLID/* GAS REACTORS 263* EXAMPLE 2:
CONVERSION OF GASEOUS HALOGENATED COMPOUNDS BY* DEHYDRATED BACTERIA 267*
INFLUENCE OF OPERATIONAL PARAMETERS ON THE DEHALOGENASE ACTIVITY OF*
WHOLE DEHYDRATED CELLS 269* EFFECT OFTEMPERATURE 269* EFFECT OF WATER
ACTIVITY 269* EFFECT OF BUFFER PH BEFORE DEHYDRATION 271* RANGE OF
SUBSTRATES 271* EXAMPLE 3: SCALING UP THE SYSTEM; APPLICATION TO
INDUSTRIAL* PRODUCTION 272* CONCLUSION 274* BIOCATALYSIS WITH
UNDISSOLVED SOLID SUBSTRATES AND PRODUCTS 279* ALESSANDRA BASSO, SARA
CANTONE, CYNTHIA EBERT, PETER J. HALLING AND LUCIA GARDOSSI INTRODUCTION
279* THE REACTION SYSTEM: CLASSIFICATION 280* THEORY 280* FACTORS
AFFECTING THE REACTIONS IN THE PRESENCE OF UNDISSOLVED*
SUBSTRATES/PRODUCTS 284* PRECIPITATION-DRIVEN SYNTHESIS OF PEPTIDES 287*
12.5 CONTENTS* IXI 12.6* PRECIPITATION-DRIVEN SYNTHESIS OF ESTERS AND
SURFACTANTS 292 12.7* THE SYNTHESIS OF SS-LACTAM ANTIBIOTICS IN THE
PRESENCE OF UNDISSOLVED SUBSTRATES 294 12.8* CONCLUSION 298 INDEX 303 |
any_adam_object | 1 |
any_adam_object_boolean | 1 |
author2 | Carrea, Giacomo |
author2_role | edt |
author2_variant | g c gc |
author_facet | Carrea, Giacomo |
building | Verbundindex |
bvnumber | BV023316530 |
callnumber-first | Q - Science |
callnumber-label | QD262 |
callnumber-raw | QD262 |
callnumber-search | QD262 |
callnumber-sort | QD 3262 |
callnumber-subject | QD - Chemistry |
classification_rvk | VK 5500 |
ctrlnum | (OCoLC)213381309 (DE-599)DNB984873333 |
dewey-full | 547.2 547.215 |
dewey-hundreds | 500 - Natural sciences and mathematics |
dewey-ones | 547 - Organic chemistry |
dewey-raw | 547.2 547.215 |
dewey-search | 547.2 547.215 |
dewey-sort | 3547.2 |
dewey-tens | 540 - Chemistry and allied sciences |
discipline | Chemie / Pharmazie |
discipline_str_mv | Chemie / Pharmazie |
format | Book |
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id | DE-604.BV023316530 |
illustrated | Illustrated |
index_date | 2024-07-02T20:52:18Z |
indexdate | 2024-07-20T09:40:38Z |
institution | BVB |
isbn | 9783527318469 3527318461 |
language | English |
oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-016500703 |
oclc_num | 213381309 |
open_access_boolean | |
owner | DE-19 DE-BY-UBM DE-703 DE-29T DE-83 DE-92 DE-11 DE-355 DE-BY-UBR |
owner_facet | DE-19 DE-BY-UBM DE-703 DE-29T DE-83 DE-92 DE-11 DE-355 DE-BY-UBR |
physical | XVII, 310 S. graph. Darst. |
publishDate | 2008 |
publishDateSearch | 2008 |
publishDateSort | 2008 |
publisher | Wiley-VCH |
record_format | marc |
spelling | Organic synthesis with enzymes in non-aqueous media ed. by Giacomo Carrea ... Weinheim Wiley-VCH 2008 XVII, 310 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Enzymen gtt Synthese (chemie) gtt Catalysis Enzymes Synthesis Organic compounds Synthesis Organische Synthese (DE-588)4075695-6 gnd rswk-swf Nichtwässriges Lösungsmittel (DE-588)4171793-4 gnd rswk-swf Enzymkatalyse (DE-588)4152480-9 gnd rswk-swf Organische Synthese (DE-588)4075695-6 s Enzymkatalyse (DE-588)4152480-9 s Nichtwässriges Lösungsmittel (DE-588)4171793-4 s DE-604 Carrea, Giacomo edt text/html http://deposit.dnb.de/cgi-bin/dokserv?id=2982639&prov=M&dok_var=1&dok_ext=htm Inhaltstext http://d-nb.info/984873333/04 Inhaltsverzeichnis OEBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016500703&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
spellingShingle | Organic synthesis with enzymes in non-aqueous media Enzymen gtt Synthese (chemie) gtt Catalysis Enzymes Synthesis Organic compounds Synthesis Organische Synthese (DE-588)4075695-6 gnd Nichtwässriges Lösungsmittel (DE-588)4171793-4 gnd Enzymkatalyse (DE-588)4152480-9 gnd |
subject_GND | (DE-588)4075695-6 (DE-588)4171793-4 (DE-588)4152480-9 |
title | Organic synthesis with enzymes in non-aqueous media |
title_auth | Organic synthesis with enzymes in non-aqueous media |
title_exact_search | Organic synthesis with enzymes in non-aqueous media |
title_exact_search_txtP | Organic synthesis with enzymes in non-aqueous media |
title_full | Organic synthesis with enzymes in non-aqueous media ed. by Giacomo Carrea ... |
title_fullStr | Organic synthesis with enzymes in non-aqueous media ed. by Giacomo Carrea ... |
title_full_unstemmed | Organic synthesis with enzymes in non-aqueous media ed. by Giacomo Carrea ... |
title_short | Organic synthesis with enzymes in non-aqueous media |
title_sort | organic synthesis with enzymes in non aqueous media |
topic | Enzymen gtt Synthese (chemie) gtt Catalysis Enzymes Synthesis Organic compounds Synthesis Organische Synthese (DE-588)4075695-6 gnd Nichtwässriges Lösungsmittel (DE-588)4171793-4 gnd Enzymkatalyse (DE-588)4152480-9 gnd |
topic_facet | Enzymen Synthese (chemie) Catalysis Enzymes Synthesis Organic compounds Synthesis Organische Synthese Nichtwässriges Lösungsmittel Enzymkatalyse |
url | http://deposit.dnb.de/cgi-bin/dokserv?id=2982639&prov=M&dok_var=1&dok_ext=htm http://d-nb.info/984873333/04 http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016500703&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
work_keys_str_mv | AT carreagiacomo organicsynthesiswithenzymesinnonaqueousmedia |