Biocatalysis for practitioners: techniques, reactions and applications
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| Format: | Buch |
| Sprache: | English |
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[2021]
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| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | Auf dem Cover: "with a foreword by Vicente Gotor" |
| Beschreibung: | xviii, 509 Seiten Illustrationen, Diagramme |
| ISBN: | 9783527346837 352734683X |
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| 020 | |a 352734683X |9 3-527-34683-X | ||
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| 245 | 1 | 0 | |a Biocatalysis for practitioners |b techniques, reactions and applications |c edited by Gonzalo de Gonzalo, Iván Lavandera |
| 264 | 1 | |a Weinheim |b Wiley-VCH |c [2021] | |
| 264 | 4 | |c © 2021 | |
| 300 | |a xviii, 509 Seiten |b Illustrationen, Diagramme | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 500 | |a Auf dem Cover: "with a foreword by Vicente Gotor" | ||
| 650 | 0 | 7 | |a Biotechnologie |0 (DE-588)4069491-4 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Biokatalyse |0 (DE-588)4393622-2 |2 gnd |9 rswk-swf |
| 653 | |a Biocatalysis | ||
| 653 | |a Biochemical Engineering | ||
| 653 | |a Biochemische Verfahrenstechnik | ||
| 653 | |a Biokatalyse | ||
| 653 | |a Chemical Engineering | ||
| 653 | |a Chemie | ||
| 653 | |a Chemische Verfahrenstechnik | ||
| 653 | |a Chemistry | ||
| 653 | |a Organic Chemistry | ||
| 653 | |a Organische Chemie | ||
| 653 | |a CG20: Biochemische Verfahrenstechnik | ||
| 653 | |a CH41: Biokatalyse | ||
| 653 | |a CH80: Organische Chemie | ||
| 655 | 7 | |0 (DE-588)4143413-4 |a Aufsatzsammlung |2 gnd-content | |
| 689 | 0 | 0 | |a Biokatalyse |0 (DE-588)4393622-2 |D s |
| 689 | 0 | 1 | |a Biotechnologie |0 (DE-588)4069491-4 |D s |
| 689 | 0 | |5 DE-604 | |
| 700 | 1 | |a Gonzalo, Gonzalo de |0 (DE-588)1149719907 |4 edt | |
| 700 | 1 | |a Lavandera, Iván |0 (DE-588)1235178722 |4 edt | |
| 700 | 1 | |a Gotor, Vicente |0 (DE-588)134010639 |4 wpr | |
| 710 | 2 | |a Wiley-VCH |0 (DE-588)16179388-5 |4 pbl | |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, PDF |z 978-3-527-82444-1 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, EPUB |z 978-3-527-82445-8 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, OBOOK |z 978-3-527-82446-5 |
| 856 | 4 | 2 | |m DNB Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=033307133&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 883 | 2 | |8 1\p |a dnb |d 20211214 |q DE-101 |u https://d-nb.info/provenance/plan#dnb | |
Datensatz im Suchindex
| _version_ | 1805075964705636352 |
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| adam_text |
CONTENTS
FOREWORD
XVII
PART
I
ENZYME
TECHNIQUES
1
1
TECHNIQUES
FOR
ENZYME
PURIFICATION
3
ADRIE
H.
WESTPHAL
AND
WILLEM
J.
H.
VAN
BERKEL
1.1
INTRODUCTION
3
1.2
TRADITIONAL
ENZYME
PURIFICATION
4
1.2.1
ION
EXCHANGE
CHROMATOGRAPHY
7
1.2.2
GEL
FILTRATION
9
1.2.3
BIO-AFFINITY
CHROMATOGRAPHY
11
1.2.4
HYDROPHOBIC
INTERACTION
CHROMATOGRAPHY
14
1.2.5
HYDROXYAPATITE
CHROMATOGRAPHY
15
1.3
EXAMPLE
OF
A
TRADITIONAL
ENZYME
PURIFICATION
PROTOCOL
17
1.4
PURIFICATION
OF
RECOMBINANT
ENZYMES
18
1.4.1
IMMOBILIZED
METAL
AFFINITY
CHROMATOGRAPHY
18
1.4.2
AFFINITY
CHROMATOGRAPHY
WITH
PROTEIN
TAGS
20
1.5
COLUMN
MATERIALS
22
1.6
CONCLUSIONS
24
REFERENCES
25
2
ENZYME
MODIFICATION
33
ANTONINO
BIUNDO,
PATRICIA
SAENZ-MENDEZ,
AND
TAMAS
GBRBE
2.1
INTRODUCTION
33
2.2
PRACTICAL
APPROACH:
EXPERIMENTAL
INFORMATION,
ANALYTICAL
METHODS,
TIPS
AND
TRICKS,
AND
EXAMPLES
34
2.2.1
DIRECTED
EVOLUTION
34
2.2.1.1
(ULTRA)HIGH-THROUGHPUT
SCREENING
AND
SELECTION
35
2.2.1.2
APPLICATIONS
OF
DIRECTED
EVOLUTION
METHODOLOGY
36
2.2.2
SEMI-RATIONAL
DESIGN
37
2.2.2.1
APPLICATIONS
OF
SEMI-RATIONAL
DESIGN
METHODOLOGY
38
2.2.3
DE
NOVO
ENZYME
DESIGN
39
VI
CONTENTS
2.23.1
APPLICATIONS
OF
DE
NOVO
ENZYME
DESIGN
METHODOLOGY
40
2.2.4
RATIONAL
ENZYME
DESIGN
40
2.2.4.1
APPLICATIONS
OF
RATIONAL
DESIGN
METHODOLOGY
41
2.3
EXPECTATIONS
AND
PERSPECTIVES
49
2.4
CONCLUDING
REMARKS
50
REFERENCES
51
3
IMMOBILIZATION
TECHNIQUES
FOR
THE
PREPARATION
OF
SUPPORTED
BIOCATALYSTS:
MAKING
BETTER
BIOCATALYSTS
THROUGH
PROTEIN
IMMOBILIZATION
63
JAVIER
ROCHA-MARTIN,
LORENA
BETANCOR,
AND
FERNANDO
LOPEZ-GALLEGO
3.1
INTRODUCTION
63
3.2
GENERAL
ASPECTS
TO
OPTIMIZE
ENZYME
IMMOBILIZATION
PROTOCOLS
64
3.2.1
CARRIER
NATURE
64
3.2.2
IMMOBILIZATION
CHEMISTRY
64
3.2.3
PROTEIN
ORIENTATION
64
3.2.4
MULTIVALENCE
OF
THE
PROTEIN
ATTACHMENT
65
3.2.5
CHEMICAL
AND
GEOMETRICAL
CONGRUENCE
65
3.2.6
ENZYME
SPATIAL
ORGANIZATION
65
3.3
TYPE
OF
CARRIERS
FOR
IMMOBILIZED
PROTEINS
66
3.3.1
TYPES
OF
MATERIALS
66
3.3.1.1
ORGANIC
MATERIALS
66
3.3.1.2
INORGANIC
MATERIALS
66
3.3.2
GEOMETRY
67
3.3.2.1
BEADS
67
33.2.2
MONOLITHS
67
33.2.3
MEMBRANES
67
3.3.3
DIMENSIONS
67
3.3.4
COMMERCIALLY
AVAILABLE
POROUS
CARRIERS
FOR
ENZYME
IMMOBILIZATION
68
3.4
IMMOBILIZATION
METHODS
AND
MANNERS
68
3.5
EVALUATION
OF
THE
ENZYME
IMMOBILIZATION
PROCESS
70
3.5.1
CONSIDERATIONS
BEFORE
IMMOBILIZATION
71
3.5.1.1
PREPARATION
OF
THE
ENZYMATIC
SOLUTION
TO
BE
IMMOBILIZED
71
3.5.1.2
STABILITY
OF
THE
SOLUBLE
ENZYME
UNDER
IMMOBILIZATION
CONDITIONS
71
3.5.2
PARAMETERS
REQUIRED
TO
DEFINE
AN
IMMOBILIZATION
PROCESS
71
3.5.2.1
IMMOBILIZATION
YIELD
72
3.5.2.2
EXPRESSED
ACTIVITY
OR
APPARENT
ACTIVITY
72
3.5.23
SPECIFIC
ACTIVITY
OF
THE
IMMOBILIZED
BIOCATALYST
73
3.6
APPLIED
EXAMPLES
OF
IMMOBILIZED
ENZYMES
73
3.6.1
CHARACTERIZATION
OF
THE
IMMOBILIZED
BIOCATALYST
74
3.6.1.1
DETERMINATION
OF
THE
CATALYTIC
ACTIVITY
OF
THE
FINAL
IMMOBILIZED
BIOCATALYST
AND
MAXIMUM
PROTEIN
LOADING
CAPACITY
74
3.6.1.2
APPARENT
KINETIC
PARAMETERS
OF
THE
IMMOBILIZED
ENZYME
76
3.6.1.3
BIOCATALYST
STABILITY
77
3.6.1.3.1
THE
HALF-LIFE
TIME
OF
BIOCATALYSTS
78
3.7
CHALLENGES
AND
OPPORTUNITIES
IN
ENZYME
IMMOBILIZATION
79
CONTENTS
VII
3.8
CONCLUSIONS
81
LIST
OF
ABBREVIATIONS
82
REFERENCES
82
4
COMPARTMENTALIZATION
IN
BIOCATALYSIS
89
ROBERT
KOURIST
AND
JAVIER
GONZALEZ-SABIN
4.1
4.2
4.3
4.4
4.5
4.6
4.7
4.8
INTRODUCTION
89
CELL
AS
A
COMPARTMENT
93
COMPARTMENTALIZATION
USING
PROTEIN
ASSEMBLIES
95
COMPARTMENTALIZATION
USING
EMULSION
AND
MICELLAR
SYSTEMS
96
COMPARTMENTALIZATION
USING
ENCAPSULATION
100
COMPARTMENTALIZATION
USING
TEA
BAGS
AND
THIMBLES
103
SEPARATION
OF
REACTION
STEPS
USING
CONTINUOUS
FLOW
105
CONCLUSIONS
AND
PROSPECTS
107
REFERENCES
108
PART
II
ENZYMES
HANDLING
AND
APPLICATIONS
113
5
PROMISCUOUS
ACTIVITY
OF
HYDROLASES
115
ERIKA
V.
M.
OROZCO
AND
ANDRE
L.
M.
PORTO
5.1
5.2
5.3
5.3.1
5.3.2
5.3.3
5.3.4
5.3.5
INTRODUCTION
115
CATALYTIC
PROMISCUITY
116
HYDROLASES
117
APPLICATIONS
OF
HYDROLASES
TO
ORGANIC
SYNTHESIS
118
LIPASES
AND
THEIR
HYDROLYSIS
MECHANISM
122
CATALYTIC
PROMISCUITY
OF
HYDROLASES
122
PROMISCUOUS
ALDOL
REACTION
CATALYZED
BY
HYDROLASES
130
ALDOL
REACTION BETWEEN 4
CYANOBENZALDEHYDE
AND
CYCLOHEXANONE
CATALYZED
BY
PORCINE
PANCREATIC
LIPASE
(PPL-II)
AND
RHIZOPUS
NIVEUS
LIPASE
(RNL)
135
5.4
CONCLUSIONS
136
REFERENCES
137
6
ENZYMES
APPLIED
TO
THE
SYNTHESIS
OF
AMINES
143
FRANCESCO
G.
MUTTI
AND
TANJA
KNAUS
6.1
6.2
6.2.1
6.2.1.1
6.2.1.2
6.2.2
6.2.2.1
INTRODUCTION
143
HYDROLASES
145
PRACTICAL
APPROACHES
WITH
HYDROLASES
145
KINETIC
RESOLUTION
145
DYNAMIC
KINETIC
RESOLUTION
146
PRACTICAL
EXAMPLES
WITH
HYDROLASES
148
KINETIC
RESOLUTION
OF
RACEMIC
A-METHYLBENZYLAMINE
THROUGH
THE
METHOXYACETYLATION
CATALYZED
BY
A
LIPASE
148
6.2.2.2
6.3
6.3.1
DYNAMIC
KINETIC
RESOLUTION
FOR
THE
SYNTHESIS
OF
NORSERTRALINE
149
AMINE
OXIDASES
149
PRACTICAL
APPROACHES
WITH
AMINE
OXIDASES
150
VIII
CONTENTS
6.3.1.1
KINETIC
RESOLUTION
AND
DERACEMIZATION
150
6.3.2
PRACTICAL
EXAMPLES
WITH
AMINE
OXIDASES
151
6.3.2.1
ONE-POT,
ONE-ENZYME
OXIDATIVE
PICTET-SPENGLER
APPROACH
COMBINED
WITH
DERACEMIZATION
151
6.3.2.2
DESYMMETRIZATION
OF
MESO-COMPOUNDS
152
6.4
TRANSAMINASES
(OR
AMINOTRANSFERASES)
152
6.4.1
PRACTICAL
APPROACHES
WITH
TRANSAMINASES
153
6.4.2
PRACTICAL
EXAMPLES
WITH
TRANSAMINASES
153
6.4.2.1
KINETIC
RESOLUTION
AND
DERACEMIZATION
153
6A.2.2
ASYMMETRIC
SYNTHESIS
FROM
PROCHIRAL
KETONE
155
6.5
AMINE
DEHYDROGENASES,
IMINE
REDUCTASES,
AND
REDUCTIVE
AMINASES
155
6.5.1
PRACTICAL
APPROACHES
WITH
AMINE
DEHYDROGENASES,
IMINE
REDUCTASES,
AND
REDUCTIVE
AMINASES
156
6.5.2
PRACTICAL
EXAMPLES
WITH
AMINE
DEHYDROGENASES,
IMINE
REDUCTASES,
AND
REDUCTIVE
AMINASES
160
6.5.2.1
IRED-CATALYZED
REDUCTIVE
AMINATION
OF
AN
ALDEHYDE
COMBINED
WITH
KR
OF
A
RACEMIC
AMINE
160
6.5.2.2
ASYMMETRIC
REDUCTIVE
AMINATION
CATALYZED
BY
AMDH
162
6.6
AMMONIA
LYASES
162
6.6.1
PRACTICAL
APPROACHES
WITH
AMMONIA
LYASES
163
6.6.1.1
ASPARTASE,
3-METHYLASPARTATE
AMMONIA
LYASE,
AND
RELATED
ENZYMES
163
6.6.1.2
AROMATIC
AMINO
ACID
AMMONIA
LYASES
AND
MUTASES
165
6.6.2
PRACTICAL
EXAMPLES
WITH
AMMONIA
LYASES
166
6.6.2.1
CHEMOENZYMATIC
SYNTHESIS
OF
(S)-2-INDOLINECARBOXYLIC
ACID
166
6.6.2.2
SYNTHESIS
OF
L-ASPARTATE
FROM
FUMARATE
166
6.6.2.3
ENZYMATIC
AND
CHEMOENZYMATIC
SYNTHESIS
OF
TOXIN
A
AND
ASPERGILLOMARASMINE
A
AND
B
166
6.7
PICTET-SPENGLERASES
167
6.7.1
PRACTICAL
APPROACHES
WITH
PICTET-SPENGLERASES
167
6.7.2
PRACTICAL
EXAMPLES
WITH
PICTET-SPENGLERASES
169
6.7.2.1
BIOCATALYTIC
SYNTHESIS
OF
(R)-HARMICINE
169
6.7.2.2
BIOCATALYTIC
SYNTHESIS
OF
(S)-TROLLINE
AND
ANALOGS
169
6.8
ENGINEERED
CYTOCHROME
P450S
(CYTOCHROME
"
P411
"
)
169
6.8.1
PRACTICAL
APPROACHES
WITH
ENGINEERED
CYTOCHROME
P450S
170
6.9
PROTOCOLS
FOR
SELECTED
REACTIONS
171
6.9.1
HYDROLASES
171
6.9.1.1
KINETIC
RESOLUTION
RAC-METHYLBENZYLAMINE
(RAC-1)
171
6.9.1.2
DYNAMIC
KINETIC
RESOLUTION
OF
NORSERTRALINE
INTERMEDIATE
(RAC-3)
171
6.9.2
MONOAMINE
OXIDASES
172
6.9.2.1
CHEMOENZYMATIC
DERACEMIZATION
OF
HARMICINE
(RAC-8)
172
6.9.3
-TRANSAMINASES
172
6.9.3.1
DERACEMIZATION
OF
MEXILETINE
(RAC-9,
KINETIC
RESOLUTION,
FOLLOWED
BY
FORMAL
REDUCTIVE
AMINATION)
172
6.9.4
IMINE
REDUCTASES
AND
AMINE
DEHYDROGENASES
172
6.9.4.1
REDUCTIVE
AMINATION OF
ALDEHYDE
(11)
WITH
KINETIC
RESOLUTION
OF
AMINE
NUCLEOPHILE
(RAC-TRANS
12)
172
CONTENTS
IX
6.9.4.2
ASYMMETRIC
REDUCTIVE
AMINATION
OF
ACETOPHENONE
(14)
USING
AMINE
DEHYDROGENASE
173
6.9.5
6.9.5.1
6.9.6
6.9.6.1
6.9.7
6.9.7.1
6.10
AMMONIA
LYASES
173
ASYMMETRIC
AMMONIA
ADDITION
TO
2'-CHLOROCINNAMIC
ACID
(17)
173
PICTET-SPENGLERASES
173
ASYMMETRIC
PICTET-SPENGLER
REACTION
WITH
STRICTOSIDINE
SYNTHASE
173
ENGINEERED
CYTOCHROME
P450S
174
INTERMOLECULAR
ALKANE
C-H
AMINATION
USING
CYTOCHROME
P41
1
174
CONCLUSIONS
174
ACKNOWLEDGMENTS
175
REFERENCES
175
7
APPLICATIONS
OF
OXIDOREDUCTASES
IN
SYNTHESIS:
A
ROADMAP
TO
ACCESS
VALUE
ADDED
PRODUCTS
181
MELANIE
HALL
7.1
7.2
7.2.1
7.2.1.1
INTRODUCTION
181
REDUCTIVE
PROCESSES
184
REDUCTION
OF
C=O
BONDS
184
SELECTION
OF
ALCOHOL
DEHYDROGENASE
(ADH)
FOR
STEREOSELECTIVE
REDUCTION
REACTIONS
185
7.2.1.1.1
7.2.1.1.2
7.2.1.1.3
'
7.2.1.1.4
7.2.1.1.5
7.2.1.2
7.2.1.2.1
7.2.1.2.2
7.2.1.2.3
7.2.1.2.4
7.2.1.2.5
7.2.2
7.2.2.1
7.2.2.2
7.2.2.2.1
7.2.2.2.2
7.2.2.3
7.2.2.3.1
7.2.23.2
7.3
7.3.1
7.3.1.1
7.3.1.1.1
7.3.1.1.2
7.3.1.1.3
7.3.1.2
ABSOLUTE
CONFIGURATION
OF
THE
PRODUCT
185
SUBSTRATE
L\PE
186
THERMOSTABILITY
187
COFACTOR
PREFERENCE
187
KITS
187
PRACTICAL
APPROACH
187
MONTELUKAST
188
ATORVASTATIN
189
DYNAMIC
KINETIC
RESOLUTIONS
189
DISPROPORTIONATION
190
REDOX
ISOMERIZATION
190
REDUCTION
OF
C=C
BONDS
191
MECHANISM
191
ENZYMES
AND
SUBSTRATES
193
ENZYMES
193
SUBSTRATES
193
PRACTICAL
APPROACH
196
STEREOCONTROL
196
(DYNAMIC)
KINETIC
RESOLUTION
197
OXIDATIVE
PROCESSES
198
OXYGENATIONS
198
BAEYER-VILLIGER
OXIDATIONS
198
REGIOPREFERENCE
200
STEREOSELECTIVITY
201
PRACTICAL
APPROACH
203
EPOXIDATION
OF
ALKENES
204
CONTENTS
7.3.2
7.3.2.1
7.3.2.2
7.3.3
7.4
HETEROATOM
OXIDATION
206
REACTION
206
SUBSTRATES
207
PEROXYGENASES:
ONE
CATALYST
-
MANY
REACTIONS
207
PROTOCOLS
FOR
SELECTED
REACTIONS
EMPLOYING
OXIDOREDUCTASES
209
7.4.1
ALCOHOL
DEHYDROGENASE
(ADH):
DISPROPORTIONATION
OF
RAC-2
PHENYLPROPANAL
209
7.4.1.1
7.4.1.2
7.4.2
BIOTRANSFORMATION
209
PRODUCT
RECOVERY
AND
PURIFICATION
210
ENE-REDUCTASE/OLD
YELLOW
ENZYME
(OYE):
DYNAMIC
KINETIC
RESOLUTION
OF
A
Y-SUBSTITUTED
LACTONE
210
7.4.2.1
7.4.2.2
7.4.3
BIOTRANSFORMATION
210
PRODUCT
RECOVERY
AND
PURIFICATION
210
BAEYER-VILLIGER
MONOOXYGENASE
(BVMO):
KINETIC
RESOLUTION
OF
A
RACEMIC
KETONE
210
7.4.3.1
7.4.3.2
7.4.4
7.4.4.1
7.4.4.2
7.5
BIO
TRANSFORMATION
211
PRODUCT
RECOVERY
AND
PURIFICATION
211
BAEYER-VILLIGER
MONOOXYGENASE
(BVMO):
ASYMMETRIC
SULFOXIDATION
211
BIOTRANSFORMATION
211
PRODUCT
RECOVERY
AND
PURIFICATION
211
CONCLUSIONS
211
ACKNOWLEDGMENTS
212
REFERENCES
212
8
GLYCOSYLTRANSFERASE
CASCADES
MADE
FIT
FOR
THE
BIOCATALYTIC
PRODUCTION
OF
NATURAL
PRODUCT
GLYCOSIDES
225
BERND
NIDETZKY
8.1
INTRODUCTION:
GLYCOSYLATED
NATURAL
PRODUCTS
AND
LELOIR
GLYCOSYLTRANSFERASES
225
8.2
8.3
8.4
8.5
8.6
8.7
GLYCOSYLATED
FLAVONOIDS
AND
NOTHOFAGIN
227
GLYCOSYLTRANSFERASE
CASCADES
FOR
BIOCATALYTIC
SYNTHESIS
OF
NOTHOFAGIN
229
ENZYME
EXPRESSION
230
SOLVENT
ENGINEERING
FOR
SUBSTRATE
SOLUBILIZATION
232
NOTHOFAGIN
PRODUCTION
AT
100
G
SCALE
233
CONCLUDING
REMARKS
237
REFERENCES
237
PART
III
WAYS
TO
IMPROVE
ENZYMATIC
TRANSFORMATIONS
245
9
APPLICATION
OF
NONAQUEOUS
MEDIA
IN
BIOCATALYSIS
247
AFIFA
A.
KOESOEMA
AND
TOMOKO
MATSUDA
9.1
9.2
INTRODUCTION
247
ADVANTAGES
AND
DISADVANTAGES
OF
REACTIONS
IN
NONAQUEOUS
MEDIA
248
CONTENTS
XI
9.3
9.4
NONAQUEOUS
MEDIA
USED
FOR
BIOCATALYSIS
248
ENZYMATIC
ACTIVITY
AND
INACTIVATION
IN
NONAQUEOUS
MEDIA
251
9.4.1
9.4.2
ENZYMATIC
ACTIVITY
IN
NONAQUEOUS
MEDIA
251
FACTORS
CAUSING
INACTIVATION
OF
ENZYMES
IN
NONAQUEOUS
MEDIA
252
9.5
PRACTICAL
APPROACHES
TO
STABILIZE
ENZYMES
IN
NONAQUEOUS
MEDIA
252
9.5.1
UTILIZATION
OF
NONAQUEOUS
MEDIA-TOLERANT
ENZYMES
OR
HOST
CELLS
252
9.5.2
9.5.3
9.5.4
9.6
ENZYME
IMMOBILIZATION
253
MODIFICATION
OF
THE
ENZYME
PREPARATION
254
PROTEIN
ENGINEERING
255
EXAMPLES
OF
BIOCATALYZED
REACTIONS
IN
SOLVENT-FREE
SYSTEMS
256
9.7
9.8
9.8.1
9.8.2
9.8.3
9.9
9.10
9.11
9.12
EXAMPLES
OF
REACTIONS
IN
MICRO-AQUEOUS
SYSTEMS
258
EXAMPLES
OF
REACTIONS
IN
BIO-BASED
LIQUIDS
260
2-METHYLTETRAHYDROFURAN
(METHF)
260
CYCLOPENTYL
METHYL
ETHER
(CPME)
261
POTENTIAL
APPLICATION
OF
OTHER
BIO-BASED
LIQUIDS
262
EXAMPLES
OF
REACTIONS
IN
LIQUID
CO
2
262
EXAMPLES
OF
REACTIONS
IN
CO
2
-EXPANDED
BIO-BASED
LIQUIDS
264
EXAMPLES
OF
REACTIONS
IN
NATURAL
DEEP
EUTECTIC
SOLVENTS
265
CONCLUSIONS
AND
FUTURE
PERSPECTIVES
267
REFERENCES
267
10
NONCONVENTIONAL
COFACTOR
REGENERATION
SYSTEMS
275
JIAFU
SHI,
YIZHOU
WU,
ZHONGYI
JIANG,
YIYING
SUN,
QIAN
HUO,
WEIRAN
LI,
YANG
ZHAO,
AND
YUQING
CHENG
10.1
10.2
10.2.1
INTRODUCTION
275
BASICS
OF
PHOTOCATALYTIC
NADH
REGENERATION
279
PROCESSES
AND
MECHANISM
ASSOCIATED
WITH
PHOTOCATALYTIC
NADH
REGENERATION
279
10.2.2
10.3
10.3.1
10.3.2
10.3.3
10.3.4
10.4
10.5
10.5.1
10.5.2
ASPECTS
OF
MEASURING
PHOTOCATALYTIC
NADH
REGENERATION
281
ADVANCEMENTS
IN
PHOTOCATALYTIC
NADH
REGENERATION
282
NATURE
PHOTOSENSITIZERS
282
ORGANIC
MOLECULAR
PHOTOSENSITIZERS
282
INORGANIC
SEMICONDUCTORS
285
ORGANIC
SEMICONDUCTORS
288
EXPECTATIONS
290
CONCLUSIONS
AND
PROSPECTS
292
CONCLUSIONS
292
PROSPECTS
292
LIST
OF
ABBREVIATIONS
292
REFERENCES
293
XII
CONTENTS
11
BIOCATALYSIS
UNDER
CONTINUOUS
FLOW
CONDITIONS
297
BRUNA
GOES
PALMA,
MARCELO
A.
DO
NASCIMENTO,
RAQUEL
A.
C.
LEDO,
OMAR
G.
PANDOLI,
AND
RODRIGO
0.
M.
A.
DE
SOUZA
11.1
INTRODUCTION
297
11.2
PRACTICAL
APPROACH
FOR
BIOCATALYSIS
UNDER
CONTINUOUS
FLOW
CONDITIONS
299
11.2.1
ESTERIFICATION
299
11.2.1.1
EXPERIMENTAL
PROCEDURE
301
11.2.2
TRANSESTERIFICATION
302
11.2.2.1
EXPERIMENTAL
PROCEDURE
303
11.2.3
KINETIC
RESOLUTIONS
303
11.2.3.1
KINETIC
RESOLUTION
OF
AMINES
EMPLOYING
LIPASES
304
11.2.3.1.1
EXPERIMENTAL
PROCEDURE
304
11.2.3.2
KINETIC
RESOLUTIONS
EMPLOYING
-TRANSAMINASES
305
11.2.3.2.1
EXPERIMENTAL
PROCEDURE
305
11.2.3.3
KINETIC
RESOLUTION
OF
ALCOHOLS
USING
LIPASES
307
11.2.3.3.1
EXPERIMENTAL
PROCEDURE
307
11.2.4
DYNAMIC
KINETIC
RESOLUTIONS
308
11.2.4.1
EXPERIMENTAL
PROCEDURE
309
11.2.5
ASYMMETRIC
SYNTHESIS
309
11.2.5.1
EXPERIMENTAL
PROCEDURE
311
11.2.5.1.1
PROTEIN
IMMOBILIZATION
311
11.2.5.1.2
ION
EXCHANGE
OF
NADPH
ON
AG-DEAE
311
11.2.5.1.3
GENERAL
PROCEDURE
FOR
THE
CONTINUOUS
ASYMMETRIC
REDUCTION
311
11.3
CONCLUSIONS
AND
PERSPECTIVE
311
REFERENCES
312
PART
IV
RECENT
TRENDS
IN
ENZYME-CATALYZED
REACTIONS
317
12
PHOTOBIOCATALYSIS
319
MARTIN
G.
LOPEZ-VIDAL,
GUILLERMO
GAMBOA,
GABRIELA
OKSDATH-MANSILLA,
AND
FABRICIO
R.
BISOGNO
12.1
INTRODUCTION
319
12.2
OXIDATIVE
PROCESSES
321
12.2.1
BAEYER-VILLIGER
OXIDATION
321
12.2.2
ALKANE
HYDROXYLATION
322
12.2.3
O-DEALKYLATION
326
12.2.4
DECARBOXYLATION
327
12.2.4.1
ALKENE
PRODUCTION
327
12.2.4.2
ALKANE
PRODUCTION
328
12.2.5
EPOXIDATION
330
12.3
REDUCTIVE
PROCESSES
332
12.3.1
CARBONYL
REDUCTION
332
12.3.2
OLEFIN
REDUCTION
336
CONTENTS
XIII
12.3.3
12.3.4
12.3.5
12.3.6
12.4
12.5
IMINE
REDUCTION
342
REDUCTIVE
AMINATION
344
DEHALOGENATION
345
DEACETOXYLATION
347
COMBINATION
OF
PHOTOOXIDATION
AND
ENZYMATIC
TRANSFORMATION
348
SUMMARY
AND
OUTLOOK
352
ABBREVIATIONS
352
REFERENCES
354
13
PRACTICAL
MULTIENZYMATIC
TRANSFORMATIONS:
COMBINING
ENZYMES
FOR
THE
ONE
POT
SYNTHESIS
OF
ORGANIC
MOLECULES
IN
A
STRAIGHTFORWARD
MANNER
361
JESUS
ALBARRDN-VELO,
SERGIO
GONZALEZ-GRANDA,
MARINA
LOPEZ-AGUDO,
AND
VICENTE
GOTOR-FERNDNDEZ
13.1
13.2
13.2.1
13.2.2
INTRODUCTION
361
NON-STEREOSELECTIVE
BIENZYMATIC
TRANSFORMATIONS
363
AMINE
SYNTHESIS
363
BIENZYMATIC
LINEAR
CASCADES
TOWARD
THE
PRODUCTION
OF
OTHER
ORGANIC
COMPOUNDS
365
13.3
13.3.1
13.3.1.1
13.3.1.2
13.3.1.3
"
13.3.1.4
13.3.2
STEREOSELECTIVE
BIENZYMATIC
TRANSFORMATIONS
367
STEREOSELECTIVE
AMINE
SYNTHESIS
THROUGH
CONCURRENT
PROCESSES
368
AMINATION
OF
ALCOHOLS
368
DERACEMIZATION
OF
AMINES
371
AMINO
ALCOHOL
SYNTHESIS
372
OTHER
BIENZYMATIC
STEREOSELECTIVE
SYNTHESIS
OF
AMINES
374
STEREOSELECTIVE
BIENZYMATIC
CASCADES
TOWARD
THE
PRODUCTION
OF
OTHER
ORGANIC
COMPOUNDS
377
13.3.2.1
13.3.2.2
13.4
13.5
SYNTHESIS
OF
ORGANIC
COMPOUNDS
OTHER
THAN
AMINO
ACIDS
377
AMINO
ACID
SYNTHESIS
383
MULTIENZYMATIC
TRANSFORMATIONS:
INCREASING
SYNTHETIC
COMPLEXITY
386
SUMMARY
AND
OUTLOOK
395
REFERENCES
395
14
CHEMOENZYMATIC
SEQUENTIAL
ONE-POT
PROTOCOLS
403
HARALD
GRBGER
14.1
14.2
INTRODUCTION:
THEORETICAL
INFORMATION
AND
CONCEPTUAL
OVERVIEW
403
STATE
OF
THE ART
IN
SEQUENTIAL
CHEMOENZYMATIC
ONE-POT
SYNTHESIS:
SELECTED
EXAMPLES
AND
HISTORICAL
OVERVIEW
ABOUT
SELECTED
CONTRIBUTIONS
406
14.2.1
SEQUENTIAL
CHEMOENZYMATIC
ONE-POT SYNTHESIS
COMBINING
A METAL-CATALYZED
REACTION
WITH
A
BIOTRANSFORMATION
406
14.2.2
SEQUENTIAL
CHEMOENZYMATIC
ONE-POT
SYNTHESIS
COMBINING
AN
ORGANOCATALYTIC
REACTION
WITH
A
BIOTRANSFORMATION
411
14.2.3
SEQUENTIAL
CHEMOENZYMATIC
ONE-POT SYNTHESIS
COMBINING
A
REACTION
CATALYZED
BY
A
HETEROGENEOUS
CHEMOCATALYST
WITH
A
BIOTRANSFORMATION
416
XIV
CONTENTS
14.2.4
SEQUENTIAL
CHEMOENZYMATIC
ONE-POT
SYNTHESIS
COMBINING
A
REACTION
CATALYZED
BY
A
HETEROGENEOUS
BIOCATALYST
WITH
A
CHEMOCATALYTIC
TRANSFORMATION
417
14.2.5
SEQUENTIAL
CHEMOENZYMATIC
ONE-POT SYNTHESIS
COMBINING
MORE
THAN
TWO
REACTIONS
418
14.3
PRACTICAL
ASPECTS
OF
THE
DEVELOPMENT
OF
SEQUENTIAL
CHEMOENZYMATIC
ONE-POT
SYNTHESES
420
14.4
CONCLUSIONS
AND
OUTLOOK
423
REFERENCES
424
PARTV
INDUSTRIAL
BIOCATALYSIS
427
15
INDUSTRIAL
PROCESSES
USING
BIOCATALYSTS
429
FLORIAN
KLEINBECK,
MAREK
MAHUT,
AND
THIERRY
SCHLAMA
15.1
15.2
15.2.1
15.2.2
15.2.3
15.2.4
15.2.5
15.2.6
15.3
INTRODUCTION
429
BIOCATALYSIS
IN
THE
PHARMACEUTICAL
INDUSTRY
430
PREGABALIN
431
VERNAKALANT
432
SITAGLIPTIN
433
ESOMEPRAZOLE
435
MONTELUKAST
436
BOCEPREVIR
439
ASPECTS
TO
CONSIDER
FOR
DEVELOPMENT
OF
A
BIOCATALYTIC
PROCESS
ON
COMMERCIAL
SCALE
-
A
CASE
STUDY
442
15.3.1
15.3.2
15.3.3
15.3.3.1
15.3.3.2
15.3.3.3
15.3.3.4
15.3.3.5
IDENTIFICATION
OF
A
SUITABLE
ENZYME
443
PROCESS
DEVELOPMENT
443
CONTROL
STRATEGY
AND
REGULATORY
CONSIDERATIONS
445
IMPURITIES
446
TYPES
OF
BIOCATALYSTS
450
TYPE
OF
EXPRESSION
SYSTEM
451
ROUTE
OF
ADMINISTRATION
451
POSITION
OF
THE
BIOCATALYTIC
STEP
IN
THE
SYNTHESIS
AND
DOWNSTREAM
TRANSFORMATIONS
451
15.3.3.6
15.3.4
15.3.4.1
15.3.4.2
15.3.4.3
15.3.5
15.3.6
15.3.7
15.3.8
SUMMARY
OF
THE
CASE
STUDY
452
HEALTH,
PROCESS
SAFETY
AND
ENVIRONMENTAL
ASPECTS
453
HEALTH
453
PROCESS
SAFETY
453
ENVIRONMENTAL
ASPECTS
454
EQUIPMENT
UTILIZATION
AND
THROUGHPUT
TIME
455
EQUIPMENT
CLEANING
455
ENZYME
RELEASE
TESTING
456
TRANSPORT
AND
STORAGE
457
CONTENTS
XV
INDEX
487
15.4
CONCLUSIONS,
EXPECTATIONS,
AND
PROSPECTS
458
ACKNOWLEDGMENTS
460
LIST
OF
ABBREVIATIONS
460
REFERENCES
461
16
ENZYMATIC
COMMERCIAL
SOURCES
467
GONZALO
DE
GONZALO
AND
IVAN
LAVANDERA
16.1
16.2
16.2.1
16.2.2
16.2.3
16.2.4
16.2.5
16.2.6
16.2.7
16.2.8
16.2.9
16.2.10
16.2.11
16.2.12
16.2.13
16.3
16.3.1
16.3.2
16.3.3
16.3.4
16.3.5
16.3.6
16.3.7
16.4
16.4.1
16.4.2
16.4.3
16.4.4
16.4.5
16.4.6
16.4.7
16.4.8
16.5
INTRODUCTION
467
EUROPEAN
COMPANIES
468
AB
ENZYMES
468
ALMAC
468
BIOCATALYSTS
469
C-LECTA
GMBH
469
ENZYMICALS
470
EVOXX
TECHNOLOGIES
GMBH
470
GECCO
471
INOFEA
AG
472
JOHNSON-MATTHEY
472
METGEN
OY
473
NOVOZYMES
474
PROZOMIX
474
ROYAL
DSM
475
AMERICAN
COMPANIES
475
CODEXIS
INC.
475
DUPONT
NUTRITION
AND
BIOSCIENCES
476
IBEX
TECHNOLOGIES
476
MP
BIOMEDICAL
477
SIGMA-ALDRICH
477
STREM
CHEMICALS,
INC.
478
WORTHINGTON
BIOCHEMICAL
CORP
479
ASIAN
ENZYME
SUPPLIERS
480
ADVANCED
ENZYMES
TECHNOLOGIES,
LTD.
480
AMANO
ENZYME
CO.,
LTD.
480
AUMGENE
BIOSCIENCES
481
ENZYMEWORKS
481
MEITO
SANGYO
CO.,
LTD.
481
ORIENTAL
YEAST
CO.,
LTD.
482
TAKABIO
482
TOYOBO
CO.,
LTD.
482
OUTLOOK
483
REFERENCES
484 |
| adam_txt |
CONTENTS
FOREWORD
XVII
PART
I
ENZYME
TECHNIQUES
1
1
TECHNIQUES
FOR
ENZYME
PURIFICATION
3
ADRIE
H.
WESTPHAL
AND
WILLEM
J.
H.
VAN
BERKEL
1.1
INTRODUCTION
3
1.2
TRADITIONAL
ENZYME
PURIFICATION
4
1.2.1
ION
EXCHANGE
CHROMATOGRAPHY
7
1.2.2
GEL
FILTRATION
9
1.2.3
BIO-AFFINITY
CHROMATOGRAPHY
11
1.2.4
HYDROPHOBIC
INTERACTION
CHROMATOGRAPHY
14
1.2.5
HYDROXYAPATITE
CHROMATOGRAPHY
15
1.3
EXAMPLE
OF
A
TRADITIONAL
ENZYME
PURIFICATION
PROTOCOL
17
1.4
PURIFICATION
OF
RECOMBINANT
ENZYMES
18
1.4.1
IMMOBILIZED
METAL
AFFINITY
CHROMATOGRAPHY
18
1.4.2
AFFINITY
CHROMATOGRAPHY
WITH
PROTEIN
TAGS
20
1.5
COLUMN
MATERIALS
22
1.6
CONCLUSIONS
24
REFERENCES
25
2
ENZYME
MODIFICATION
33
ANTONINO
BIUNDO,
PATRICIA
SAENZ-MENDEZ,
AND
TAMAS
GBRBE
2.1
INTRODUCTION
33
2.2
PRACTICAL
APPROACH:
EXPERIMENTAL
INFORMATION,
ANALYTICAL
METHODS,
TIPS
AND
TRICKS,
AND
EXAMPLES
34
2.2.1
DIRECTED
EVOLUTION
34
2.2.1.1
(ULTRA)HIGH-THROUGHPUT
SCREENING
AND
SELECTION
35
2.2.1.2
APPLICATIONS
OF
DIRECTED
EVOLUTION
METHODOLOGY
36
2.2.2
SEMI-RATIONAL
DESIGN
37
2.2.2.1
APPLICATIONS
OF
SEMI-RATIONAL
DESIGN
METHODOLOGY
38
2.2.3
DE
NOVO
ENZYME
DESIGN
39
VI
CONTENTS
2.23.1
APPLICATIONS
OF
DE
NOVO
ENZYME
DESIGN
METHODOLOGY
40
2.2.4
RATIONAL
ENZYME
DESIGN
40
2.2.4.1
APPLICATIONS
OF
RATIONAL
DESIGN
METHODOLOGY
41
2.3
EXPECTATIONS
AND
PERSPECTIVES
49
2.4
CONCLUDING
REMARKS
50
REFERENCES
51
3
IMMOBILIZATION
TECHNIQUES
FOR
THE
PREPARATION
OF
SUPPORTED
BIOCATALYSTS:
MAKING
BETTER
BIOCATALYSTS
THROUGH
PROTEIN
IMMOBILIZATION
63
JAVIER
ROCHA-MARTIN,
LORENA
BETANCOR,
AND
FERNANDO
LOPEZ-GALLEGO
3.1
INTRODUCTION
63
3.2
GENERAL
ASPECTS
TO
OPTIMIZE
ENZYME
IMMOBILIZATION
PROTOCOLS
64
3.2.1
CARRIER
NATURE
64
3.2.2
IMMOBILIZATION
CHEMISTRY
64
3.2.3
PROTEIN
ORIENTATION
64
3.2.4
MULTIVALENCE
OF
THE
PROTEIN
ATTACHMENT
65
3.2.5
CHEMICAL
AND
GEOMETRICAL
CONGRUENCE
65
3.2.6
ENZYME
SPATIAL
ORGANIZATION
65
3.3
TYPE
OF
CARRIERS
FOR
IMMOBILIZED
PROTEINS
66
3.3.1
TYPES
OF
MATERIALS
66
3.3.1.1
ORGANIC
MATERIALS
66
3.3.1.2
INORGANIC
MATERIALS
66
3.3.2
GEOMETRY
67
3.3.2.1
BEADS
67
33.2.2
MONOLITHS
67
33.2.3
MEMBRANES
67
3.3.3
DIMENSIONS
67
3.3.4
COMMERCIALLY
AVAILABLE
POROUS
CARRIERS
FOR
ENZYME
IMMOBILIZATION
68
3.4
IMMOBILIZATION
METHODS
AND
MANNERS
68
3.5
EVALUATION
OF
THE
ENZYME
IMMOBILIZATION
PROCESS
70
3.5.1
CONSIDERATIONS
BEFORE
IMMOBILIZATION
71
3.5.1.1
PREPARATION
OF
THE
ENZYMATIC
SOLUTION
TO
BE
IMMOBILIZED
71
3.5.1.2
STABILITY
OF
THE
SOLUBLE
ENZYME
UNDER
IMMOBILIZATION
CONDITIONS
71
3.5.2
PARAMETERS
REQUIRED
TO
DEFINE
AN
IMMOBILIZATION
PROCESS
71
3.5.2.1
IMMOBILIZATION
YIELD
72
3.5.2.2
EXPRESSED
ACTIVITY
OR
APPARENT
ACTIVITY
72
3.5.23
SPECIFIC
ACTIVITY
OF
THE
IMMOBILIZED
BIOCATALYST
73
3.6
APPLIED
EXAMPLES
OF
IMMOBILIZED
ENZYMES
73
3.6.1
CHARACTERIZATION
OF
THE
IMMOBILIZED
BIOCATALYST
74
3.6.1.1
DETERMINATION
OF
THE
CATALYTIC
ACTIVITY
OF
THE
FINAL
IMMOBILIZED
BIOCATALYST
AND
MAXIMUM
PROTEIN
LOADING
CAPACITY
74
3.6.1.2
APPARENT
KINETIC
PARAMETERS
OF
THE
IMMOBILIZED
ENZYME
76
3.6.1.3
BIOCATALYST
STABILITY
77
3.6.1.3.1
THE
HALF-LIFE
TIME
OF
BIOCATALYSTS
78
3.7
CHALLENGES
AND
OPPORTUNITIES
IN
ENZYME
IMMOBILIZATION
79
CONTENTS
VII
3.8
CONCLUSIONS
81
LIST
OF
ABBREVIATIONS
82
REFERENCES
82
4
COMPARTMENTALIZATION
IN
BIOCATALYSIS
89
ROBERT
KOURIST
AND
JAVIER
GONZALEZ-SABIN
4.1
4.2
4.3
4.4
4.5
4.6
4.7
4.8
INTRODUCTION
89
CELL
AS
A
COMPARTMENT
93
COMPARTMENTALIZATION
USING
PROTEIN
ASSEMBLIES
95
COMPARTMENTALIZATION
USING
EMULSION
AND
MICELLAR
SYSTEMS
96
COMPARTMENTALIZATION
USING
ENCAPSULATION
100
COMPARTMENTALIZATION
USING
TEA
BAGS
AND
THIMBLES
103
SEPARATION
OF
REACTION
STEPS
USING
CONTINUOUS
FLOW
105
CONCLUSIONS
AND
PROSPECTS
107
REFERENCES
108
PART
II
ENZYMES
HANDLING
AND
APPLICATIONS
113
5
PROMISCUOUS
ACTIVITY
OF
HYDROLASES
115
ERIKA
V.
M.
OROZCO
AND
ANDRE
L.
M.
PORTO
5.1
5.2
5.3
5.3.1
5.3.2
5.3.3
5.3.4
5.3.5
INTRODUCTION
115
CATALYTIC
PROMISCUITY
116
HYDROLASES
117
APPLICATIONS
OF
HYDROLASES
TO
ORGANIC
SYNTHESIS
118
LIPASES
AND
THEIR
HYDROLYSIS
MECHANISM
122
CATALYTIC
PROMISCUITY
OF
HYDROLASES
122
PROMISCUOUS
ALDOL
REACTION
CATALYZED
BY
HYDROLASES
130
ALDOL
REACTION BETWEEN 4
CYANOBENZALDEHYDE
AND
CYCLOHEXANONE
CATALYZED
BY
PORCINE
PANCREATIC
LIPASE
(PPL-II)
AND
RHIZOPUS
NIVEUS
LIPASE
(RNL)
135
5.4
CONCLUSIONS
136
REFERENCES
137
6
ENZYMES
APPLIED
TO
THE
SYNTHESIS
OF
AMINES
143
FRANCESCO
G.
MUTTI
AND
TANJA
KNAUS
6.1
6.2
6.2.1
6.2.1.1
6.2.1.2
6.2.2
6.2.2.1
INTRODUCTION
143
HYDROLASES
145
PRACTICAL
APPROACHES
WITH
HYDROLASES
145
KINETIC
RESOLUTION
145
DYNAMIC
KINETIC
RESOLUTION
146
PRACTICAL
EXAMPLES
WITH
HYDROLASES
148
KINETIC
RESOLUTION
OF
RACEMIC
A-METHYLBENZYLAMINE
THROUGH
THE
METHOXYACETYLATION
CATALYZED
BY
A
LIPASE
148
6.2.2.2
6.3
6.3.1
DYNAMIC
KINETIC
RESOLUTION
FOR
THE
SYNTHESIS
OF
NORSERTRALINE
149
AMINE
OXIDASES
149
PRACTICAL
APPROACHES
WITH
AMINE
OXIDASES
150
VIII
CONTENTS
6.3.1.1
KINETIC
RESOLUTION
AND
DERACEMIZATION
150
6.3.2
PRACTICAL
EXAMPLES
WITH
AMINE
OXIDASES
151
6.3.2.1
ONE-POT,
ONE-ENZYME
OXIDATIVE
PICTET-SPENGLER
APPROACH
COMBINED
WITH
DERACEMIZATION
151
6.3.2.2
DESYMMETRIZATION
OF
MESO-COMPOUNDS
152
6.4
TRANSAMINASES
(OR
AMINOTRANSFERASES)
152
6.4.1
PRACTICAL
APPROACHES
WITH
TRANSAMINASES
153
6.4.2
PRACTICAL
EXAMPLES
WITH
TRANSAMINASES
153
6.4.2.1
KINETIC
RESOLUTION
AND
DERACEMIZATION
153
6A.2.2
ASYMMETRIC
SYNTHESIS
FROM
PROCHIRAL
KETONE
155
6.5
AMINE
DEHYDROGENASES,
IMINE
REDUCTASES,
AND
REDUCTIVE
AMINASES
155
6.5.1
PRACTICAL
APPROACHES
WITH
AMINE
DEHYDROGENASES,
IMINE
REDUCTASES,
AND
REDUCTIVE
AMINASES
156
6.5.2
PRACTICAL
EXAMPLES
WITH
AMINE
DEHYDROGENASES,
IMINE
REDUCTASES,
AND
REDUCTIVE
AMINASES
160
6.5.2.1
IRED-CATALYZED
REDUCTIVE
AMINATION
OF
AN
ALDEHYDE
COMBINED
WITH
KR
OF
A
RACEMIC
AMINE
160
6.5.2.2
ASYMMETRIC
REDUCTIVE
AMINATION
CATALYZED
BY
AMDH
162
6.6
AMMONIA
LYASES
162
6.6.1
PRACTICAL
APPROACHES
WITH
AMMONIA
LYASES
163
6.6.1.1
ASPARTASE,
3-METHYLASPARTATE
AMMONIA
LYASE,
AND
RELATED
ENZYMES
163
6.6.1.2
AROMATIC
AMINO
ACID
AMMONIA
LYASES
AND
MUTASES
165
6.6.2
PRACTICAL
EXAMPLES
WITH
AMMONIA
LYASES
166
6.6.2.1
CHEMOENZYMATIC
SYNTHESIS
OF
(S)-2-INDOLINECARBOXYLIC
ACID
166
6.6.2.2
SYNTHESIS
OF
L-ASPARTATE
FROM
FUMARATE
166
6.6.2.3
ENZYMATIC
AND
CHEMOENZYMATIC
SYNTHESIS
OF
TOXIN
A
AND
ASPERGILLOMARASMINE
A
AND
B
166
6.7
PICTET-SPENGLERASES
167
6.7.1
PRACTICAL
APPROACHES
WITH
PICTET-SPENGLERASES
167
6.7.2
PRACTICAL
EXAMPLES
WITH
PICTET-SPENGLERASES
169
6.7.2.1
BIOCATALYTIC
SYNTHESIS
OF
(R)-HARMICINE
169
6.7.2.2
BIOCATALYTIC
SYNTHESIS
OF
(S)-TROLLINE
AND
ANALOGS
169
6.8
ENGINEERED
CYTOCHROME
P450S
(CYTOCHROME
"
P411
"
)
169
6.8.1
PRACTICAL
APPROACHES
WITH
ENGINEERED
CYTOCHROME
P450S
170
6.9
PROTOCOLS
FOR
SELECTED
REACTIONS
171
6.9.1
HYDROLASES
171
6.9.1.1
KINETIC
RESOLUTION
RAC-METHYLBENZYLAMINE
(RAC-1)
171
6.9.1.2
DYNAMIC
KINETIC
RESOLUTION
OF
NORSERTRALINE
INTERMEDIATE
(RAC-3)
171
6.9.2
MONOAMINE
OXIDASES
172
6.9.2.1
CHEMOENZYMATIC
DERACEMIZATION
OF
HARMICINE
(RAC-8)
172
6.9.3
-TRANSAMINASES
172
6.9.3.1
DERACEMIZATION
OF
MEXILETINE
(RAC-9,
KINETIC
RESOLUTION,
FOLLOWED
BY
FORMAL
REDUCTIVE
AMINATION)
172
6.9.4
IMINE
REDUCTASES
AND
AMINE
DEHYDROGENASES
172
6.9.4.1
REDUCTIVE
AMINATION OF
ALDEHYDE
(11)
WITH
KINETIC
RESOLUTION
OF
AMINE
NUCLEOPHILE
(RAC-TRANS
12)
172
CONTENTS
IX
6.9.4.2
ASYMMETRIC
REDUCTIVE
AMINATION
OF
ACETOPHENONE
(14)
USING
AMINE
DEHYDROGENASE
173
6.9.5
6.9.5.1
6.9.6
6.9.6.1
6.9.7
6.9.7.1
6.10
AMMONIA
LYASES
173
ASYMMETRIC
AMMONIA
ADDITION
TO
2'-CHLOROCINNAMIC
ACID
(17)
173
PICTET-SPENGLERASES
173
ASYMMETRIC
PICTET-SPENGLER
REACTION
WITH
STRICTOSIDINE
SYNTHASE
173
ENGINEERED
CYTOCHROME
P450S
174
INTERMOLECULAR
ALKANE
C-H
AMINATION
USING
CYTOCHROME
P41
1
174
CONCLUSIONS
174
ACKNOWLEDGMENTS
175
REFERENCES
175
7
APPLICATIONS
OF
OXIDOREDUCTASES
IN
SYNTHESIS:
A
ROADMAP
TO
ACCESS
VALUE
ADDED
PRODUCTS
181
MELANIE
HALL
7.1
7.2
7.2.1
7.2.1.1
INTRODUCTION
181
REDUCTIVE
PROCESSES
184
REDUCTION
OF
C=O
BONDS
184
SELECTION
OF
ALCOHOL
DEHYDROGENASE
(ADH)
FOR
STEREOSELECTIVE
REDUCTION
REACTIONS
185
7.2.1.1.1
7.2.1.1.2
7.2.1.1.3
'
7.2.1.1.4
7.2.1.1.5
7.2.1.2
7.2.1.2.1
7.2.1.2.2
7.2.1.2.3
7.2.1.2.4
7.2.1.2.5
7.2.2
7.2.2.1
7.2.2.2
7.2.2.2.1
7.2.2.2.2
7.2.2.3
7.2.2.3.1
7.2.23.2
7.3
7.3.1
7.3.1.1
7.3.1.1.1
7.3.1.1.2
7.3.1.1.3
7.3.1.2
ABSOLUTE
CONFIGURATION
OF
THE
PRODUCT
185
SUBSTRATE
L\PE
186
THERMOSTABILITY
187
COFACTOR
PREFERENCE
187
KITS
187
PRACTICAL
APPROACH
187
MONTELUKAST
188
ATORVASTATIN
189
DYNAMIC
KINETIC
RESOLUTIONS
189
DISPROPORTIONATION
190
REDOX
ISOMERIZATION
190
REDUCTION
OF
C=C
BONDS
191
MECHANISM
191
ENZYMES
AND
SUBSTRATES
193
ENZYMES
193
SUBSTRATES
193
PRACTICAL
APPROACH
196
STEREOCONTROL
196
(DYNAMIC)
KINETIC
RESOLUTION
197
OXIDATIVE
PROCESSES
198
OXYGENATIONS
198
BAEYER-VILLIGER
OXIDATIONS
198
REGIOPREFERENCE
200
STEREOSELECTIVITY
201
PRACTICAL
APPROACH
203
EPOXIDATION
OF
ALKENES
204
CONTENTS
7.3.2
7.3.2.1
7.3.2.2
7.3.3
7.4
HETEROATOM
OXIDATION
206
REACTION
206
SUBSTRATES
207
PEROXYGENASES:
ONE
CATALYST
-
MANY
REACTIONS
207
PROTOCOLS
FOR
SELECTED
REACTIONS
EMPLOYING
OXIDOREDUCTASES
209
7.4.1
ALCOHOL
DEHYDROGENASE
(ADH):
DISPROPORTIONATION
OF
RAC-2
PHENYLPROPANAL
209
7.4.1.1
7.4.1.2
7.4.2
BIOTRANSFORMATION
209
PRODUCT
RECOVERY
AND
PURIFICATION
210
ENE-REDUCTASE/OLD
YELLOW
ENZYME
(OYE):
DYNAMIC
KINETIC
RESOLUTION
OF
A
Y-SUBSTITUTED
LACTONE
210
7.4.2.1
7.4.2.2
7.4.3
BIOTRANSFORMATION
210
PRODUCT
RECOVERY
AND
PURIFICATION
210
BAEYER-VILLIGER
MONOOXYGENASE
(BVMO):
KINETIC
RESOLUTION
OF
A
RACEMIC
KETONE
210
7.4.3.1
7.4.3.2
7.4.4
7.4.4.1
7.4.4.2
7.5
BIO
TRANSFORMATION
211
PRODUCT
RECOVERY
AND
PURIFICATION
211
BAEYER-VILLIGER
MONOOXYGENASE
(BVMO):
ASYMMETRIC
SULFOXIDATION
211
BIOTRANSFORMATION
211
PRODUCT
RECOVERY
AND
PURIFICATION
211
CONCLUSIONS
211
ACKNOWLEDGMENTS
212
REFERENCES
212
8
GLYCOSYLTRANSFERASE
CASCADES
MADE
FIT
FOR
THE
BIOCATALYTIC
PRODUCTION
OF
NATURAL
PRODUCT
GLYCOSIDES
225
BERND
NIDETZKY
8.1
INTRODUCTION:
GLYCOSYLATED
NATURAL
PRODUCTS
AND
LELOIR
GLYCOSYLTRANSFERASES
225
8.2
8.3
8.4
8.5
8.6
8.7
GLYCOSYLATED
FLAVONOIDS
AND
NOTHOFAGIN
227
GLYCOSYLTRANSFERASE
CASCADES
FOR
BIOCATALYTIC
SYNTHESIS
OF
NOTHOFAGIN
229
ENZYME
EXPRESSION
230
SOLVENT
ENGINEERING
FOR
SUBSTRATE
SOLUBILIZATION
232
NOTHOFAGIN
PRODUCTION
AT
100
G
SCALE
233
CONCLUDING
REMARKS
237
REFERENCES
237
PART
III
WAYS
TO
IMPROVE
ENZYMATIC
TRANSFORMATIONS
245
9
APPLICATION
OF
NONAQUEOUS
MEDIA
IN
BIOCATALYSIS
247
AFIFA
A.
KOESOEMA
AND
TOMOKO
MATSUDA
9.1
9.2
INTRODUCTION
247
ADVANTAGES
AND
DISADVANTAGES
OF
REACTIONS
IN
NONAQUEOUS
MEDIA
248
CONTENTS
XI
9.3
9.4
NONAQUEOUS
MEDIA
USED
FOR
BIOCATALYSIS
248
ENZYMATIC
ACTIVITY
AND
INACTIVATION
IN
NONAQUEOUS
MEDIA
251
9.4.1
9.4.2
ENZYMATIC
ACTIVITY
IN
NONAQUEOUS
MEDIA
251
FACTORS
CAUSING
INACTIVATION
OF
ENZYMES
IN
NONAQUEOUS
MEDIA
252
9.5
PRACTICAL
APPROACHES
TO
STABILIZE
ENZYMES
IN
NONAQUEOUS
MEDIA
252
9.5.1
UTILIZATION
OF
NONAQUEOUS
MEDIA-TOLERANT
ENZYMES
OR
HOST
CELLS
252
9.5.2
9.5.3
9.5.4
9.6
ENZYME
IMMOBILIZATION
253
MODIFICATION
OF
THE
ENZYME
PREPARATION
254
PROTEIN
ENGINEERING
255
EXAMPLES
OF
BIOCATALYZED
REACTIONS
IN
SOLVENT-FREE
SYSTEMS
256
9.7
9.8
9.8.1
9.8.2
9.8.3
9.9
9.10
9.11
9.12
EXAMPLES
OF
REACTIONS
IN
MICRO-AQUEOUS
SYSTEMS
258
EXAMPLES
OF
REACTIONS
IN
BIO-BASED
LIQUIDS
260
2-METHYLTETRAHYDROFURAN
(METHF)
260
CYCLOPENTYL
METHYL
ETHER
(CPME)
261
POTENTIAL
APPLICATION
OF
OTHER
BIO-BASED
LIQUIDS
262
EXAMPLES
OF
REACTIONS
IN
LIQUID
CO
2
262
EXAMPLES
OF
REACTIONS
IN
CO
2
-EXPANDED
BIO-BASED
LIQUIDS
264
EXAMPLES
OF
REACTIONS
IN
NATURAL
DEEP
EUTECTIC
SOLVENTS
265
CONCLUSIONS
AND
FUTURE
PERSPECTIVES
267
REFERENCES
267
10
NONCONVENTIONAL
COFACTOR
REGENERATION
SYSTEMS
275
JIAFU
SHI,
YIZHOU
WU,
ZHONGYI
JIANG,
YIYING
SUN,
QIAN
HUO,
WEIRAN
LI,
YANG
ZHAO,
AND
YUQING
CHENG
10.1
10.2
10.2.1
INTRODUCTION
275
BASICS
OF
PHOTOCATALYTIC
NADH
REGENERATION
279
PROCESSES
AND
MECHANISM
ASSOCIATED
WITH
PHOTOCATALYTIC
NADH
REGENERATION
279
10.2.2
10.3
10.3.1
10.3.2
10.3.3
10.3.4
10.4
10.5
10.5.1
10.5.2
ASPECTS
OF
MEASURING
PHOTOCATALYTIC
NADH
REGENERATION
281
ADVANCEMENTS
IN
PHOTOCATALYTIC
NADH
REGENERATION
282
NATURE
PHOTOSENSITIZERS
282
ORGANIC
MOLECULAR
PHOTOSENSITIZERS
282
INORGANIC
SEMICONDUCTORS
285
ORGANIC
SEMICONDUCTORS
288
EXPECTATIONS
290
CONCLUSIONS
AND
PROSPECTS
292
CONCLUSIONS
292
PROSPECTS
292
LIST
OF
ABBREVIATIONS
292
REFERENCES
293
XII
CONTENTS
11
BIOCATALYSIS
UNDER
CONTINUOUS
FLOW
CONDITIONS
297
BRUNA
GOES
PALMA,
MARCELO
A.
DO
NASCIMENTO,
RAQUEL
A.
C.
LEDO,
OMAR
G.
PANDOLI,
AND
RODRIGO
0.
M.
A.
DE
SOUZA
11.1
INTRODUCTION
297
11.2
PRACTICAL
APPROACH
FOR
BIOCATALYSIS
UNDER
CONTINUOUS
FLOW
CONDITIONS
299
11.2.1
ESTERIFICATION
299
11.2.1.1
EXPERIMENTAL
PROCEDURE
301
11.2.2
TRANSESTERIFICATION
302
11.2.2.1
EXPERIMENTAL
PROCEDURE
303
11.2.3
KINETIC
RESOLUTIONS
303
11.2.3.1
KINETIC
RESOLUTION
OF
AMINES
EMPLOYING
LIPASES
304
11.2.3.1.1
EXPERIMENTAL
PROCEDURE
304
11.2.3.2
KINETIC
RESOLUTIONS
EMPLOYING
-TRANSAMINASES
305
11.2.3.2.1
EXPERIMENTAL
PROCEDURE
305
11.2.3.3
KINETIC
RESOLUTION
OF
ALCOHOLS
USING
LIPASES
307
11.2.3.3.1
EXPERIMENTAL
PROCEDURE
307
11.2.4
DYNAMIC
KINETIC
RESOLUTIONS
308
11.2.4.1
EXPERIMENTAL
PROCEDURE
309
11.2.5
ASYMMETRIC
SYNTHESIS
309
11.2.5.1
EXPERIMENTAL
PROCEDURE
311
11.2.5.1.1
PROTEIN
IMMOBILIZATION
311
11.2.5.1.2
ION
EXCHANGE
OF
NADPH
ON
AG-DEAE
311
11.2.5.1.3
GENERAL
PROCEDURE
FOR
THE
CONTINUOUS
ASYMMETRIC
REDUCTION
311
11.3
CONCLUSIONS
AND
PERSPECTIVE
311
REFERENCES
312
PART
IV
RECENT
TRENDS
IN
ENZYME-CATALYZED
REACTIONS
317
12
PHOTOBIOCATALYSIS
319
MARTIN
G.
LOPEZ-VIDAL,
GUILLERMO
GAMBOA,
GABRIELA
OKSDATH-MANSILLA,
AND
FABRICIO
R.
BISOGNO
12.1
INTRODUCTION
319
12.2
OXIDATIVE
PROCESSES
321
12.2.1
BAEYER-VILLIGER
OXIDATION
321
12.2.2
ALKANE
HYDROXYLATION
322
12.2.3
O-DEALKYLATION
326
12.2.4
DECARBOXYLATION
327
12.2.4.1
ALKENE
PRODUCTION
327
12.2.4.2
ALKANE
PRODUCTION
328
12.2.5
EPOXIDATION
330
12.3
REDUCTIVE
PROCESSES
332
12.3.1
CARBONYL
REDUCTION
332
12.3.2
OLEFIN
REDUCTION
336
CONTENTS
XIII
12.3.3
12.3.4
12.3.5
12.3.6
12.4
12.5
IMINE
REDUCTION
342
REDUCTIVE
AMINATION
344
DEHALOGENATION
345
DEACETOXYLATION
347
COMBINATION
OF
PHOTOOXIDATION
AND
ENZYMATIC
TRANSFORMATION
348
SUMMARY
AND
OUTLOOK
352
ABBREVIATIONS
352
REFERENCES
354
13
PRACTICAL
MULTIENZYMATIC
TRANSFORMATIONS:
COMBINING
ENZYMES
FOR
THE
ONE
POT
SYNTHESIS
OF
ORGANIC
MOLECULES
IN
A
STRAIGHTFORWARD
MANNER
361
JESUS
ALBARRDN-VELO,
SERGIO
GONZALEZ-GRANDA,
MARINA
LOPEZ-AGUDO,
AND
VICENTE
GOTOR-FERNDNDEZ
13.1
13.2
13.2.1
13.2.2
INTRODUCTION
361
NON-STEREOSELECTIVE
BIENZYMATIC
TRANSFORMATIONS
363
AMINE
SYNTHESIS
363
BIENZYMATIC
LINEAR
CASCADES
TOWARD
THE
PRODUCTION
OF
OTHER
ORGANIC
COMPOUNDS
365
13.3
13.3.1
13.3.1.1
13.3.1.2
13.3.1.3
"
13.3.1.4
13.3.2
STEREOSELECTIVE
BIENZYMATIC
TRANSFORMATIONS
367
STEREOSELECTIVE
AMINE
SYNTHESIS
THROUGH
CONCURRENT
PROCESSES
368
AMINATION
OF
ALCOHOLS
368
DERACEMIZATION
OF
AMINES
371
AMINO
ALCOHOL
SYNTHESIS
372
OTHER
BIENZYMATIC
STEREOSELECTIVE
SYNTHESIS
OF
AMINES
374
STEREOSELECTIVE
BIENZYMATIC
CASCADES
TOWARD
THE
PRODUCTION
OF
OTHER
ORGANIC
COMPOUNDS
377
13.3.2.1
13.3.2.2
13.4
13.5
SYNTHESIS
OF
ORGANIC
COMPOUNDS
OTHER
THAN
AMINO
ACIDS
377
AMINO
ACID
SYNTHESIS
383
MULTIENZYMATIC
TRANSFORMATIONS:
INCREASING
SYNTHETIC
COMPLEXITY
386
SUMMARY
AND
OUTLOOK
395
REFERENCES
395
14
CHEMOENZYMATIC
SEQUENTIAL
ONE-POT
PROTOCOLS
403
HARALD
GRBGER
14.1
14.2
INTRODUCTION:
THEORETICAL
INFORMATION
AND
CONCEPTUAL
OVERVIEW
403
STATE
OF
THE ART
IN
SEQUENTIAL
CHEMOENZYMATIC
ONE-POT
SYNTHESIS:
SELECTED
EXAMPLES
AND
HISTORICAL
OVERVIEW
ABOUT
SELECTED
CONTRIBUTIONS
406
14.2.1
SEQUENTIAL
CHEMOENZYMATIC
ONE-POT SYNTHESIS
COMBINING
A METAL-CATALYZED
REACTION
WITH
A
BIOTRANSFORMATION
406
14.2.2
SEQUENTIAL
CHEMOENZYMATIC
ONE-POT
SYNTHESIS
COMBINING
AN
ORGANOCATALYTIC
REACTION
WITH
A
BIOTRANSFORMATION
411
14.2.3
SEQUENTIAL
CHEMOENZYMATIC
ONE-POT SYNTHESIS
COMBINING
A
REACTION
CATALYZED
BY
A
HETEROGENEOUS
CHEMOCATALYST
WITH
A
BIOTRANSFORMATION
416
XIV
CONTENTS
14.2.4
SEQUENTIAL
CHEMOENZYMATIC
ONE-POT
SYNTHESIS
COMBINING
A
REACTION
CATALYZED
BY
A
HETEROGENEOUS
BIOCATALYST
WITH
A
CHEMOCATALYTIC
TRANSFORMATION
417
14.2.5
SEQUENTIAL
CHEMOENZYMATIC
ONE-POT SYNTHESIS
COMBINING
MORE
THAN
TWO
REACTIONS
418
14.3
PRACTICAL
ASPECTS
OF
THE
DEVELOPMENT
OF
SEQUENTIAL
CHEMOENZYMATIC
ONE-POT
SYNTHESES
420
14.4
CONCLUSIONS
AND
OUTLOOK
423
REFERENCES
424
PARTV
INDUSTRIAL
BIOCATALYSIS
427
15
INDUSTRIAL
PROCESSES
USING
BIOCATALYSTS
429
FLORIAN
KLEINBECK,
MAREK
MAHUT,
AND
THIERRY
SCHLAMA
15.1
15.2
15.2.1
15.2.2
15.2.3
15.2.4
15.2.5
15.2.6
15.3
INTRODUCTION
429
BIOCATALYSIS
IN
THE
PHARMACEUTICAL
INDUSTRY
430
PREGABALIN
431
VERNAKALANT
432
SITAGLIPTIN
433
ESOMEPRAZOLE
435
MONTELUKAST
436
BOCEPREVIR
439
ASPECTS
TO
CONSIDER
FOR
DEVELOPMENT
OF
A
BIOCATALYTIC
PROCESS
ON
COMMERCIAL
SCALE
-
A
CASE
STUDY
442
15.3.1
15.3.2
15.3.3
15.3.3.1
15.3.3.2
15.3.3.3
15.3.3.4
15.3.3.5
IDENTIFICATION
OF
A
SUITABLE
ENZYME
443
PROCESS
DEVELOPMENT
443
CONTROL
STRATEGY
AND
REGULATORY
CONSIDERATIONS
445
IMPURITIES
446
TYPES
OF
BIOCATALYSTS
450
TYPE
OF
EXPRESSION
SYSTEM
451
ROUTE
OF
ADMINISTRATION
451
POSITION
OF
THE
BIOCATALYTIC
STEP
IN
THE
SYNTHESIS
AND
DOWNSTREAM
TRANSFORMATIONS
451
15.3.3.6
15.3.4
15.3.4.1
15.3.4.2
15.3.4.3
15.3.5
15.3.6
15.3.7
15.3.8
SUMMARY
OF
THE
CASE
STUDY
452
HEALTH,
PROCESS
SAFETY
AND
ENVIRONMENTAL
ASPECTS
453
HEALTH
453
PROCESS
SAFETY
453
ENVIRONMENTAL
ASPECTS
454
EQUIPMENT
UTILIZATION
AND
THROUGHPUT
TIME
455
EQUIPMENT
CLEANING
455
ENZYME
RELEASE
TESTING
456
TRANSPORT
AND
STORAGE
457
CONTENTS
XV
INDEX
487
15.4
CONCLUSIONS,
EXPECTATIONS,
AND
PROSPECTS
458
ACKNOWLEDGMENTS
460
LIST
OF
ABBREVIATIONS
460
REFERENCES
461
16
ENZYMATIC
COMMERCIAL
SOURCES
467
GONZALO
DE
GONZALO
AND
IVAN
LAVANDERA
16.1
16.2
16.2.1
16.2.2
16.2.3
16.2.4
16.2.5
16.2.6
16.2.7
16.2.8
16.2.9
16.2.10
16.2.11
16.2.12
16.2.13
16.3
16.3.1
16.3.2
16.3.3
16.3.4
16.3.5
16.3.6
16.3.7
16.4
16.4.1
16.4.2
16.4.3
16.4.4
16.4.5
16.4.6
16.4.7
16.4.8
16.5
INTRODUCTION
467
EUROPEAN
COMPANIES
468
AB
ENZYMES
468
ALMAC
468
BIOCATALYSTS
469
C-LECTA
GMBH
469
ENZYMICALS
470
EVOXX
TECHNOLOGIES
GMBH
470
GECCO
471
INOFEA
AG
472
JOHNSON-MATTHEY
472
METGEN
OY
473
NOVOZYMES
474
PROZOMIX
474
ROYAL
DSM
475
AMERICAN
COMPANIES
475
CODEXIS
INC.
475
DUPONT
NUTRITION
AND
BIOSCIENCES
476
IBEX
TECHNOLOGIES
476
MP
BIOMEDICAL
477
SIGMA-ALDRICH
477
STREM
CHEMICALS,
INC.
478
WORTHINGTON
BIOCHEMICAL
CORP
479
ASIAN
ENZYME
SUPPLIERS
480
ADVANCED
ENZYMES
TECHNOLOGIES,
LTD.
480
AMANO
ENZYME
CO.,
LTD.
480
AUMGENE
BIOSCIENCES
481
ENZYMEWORKS
481
MEITO
SANGYO
CO.,
LTD.
481
ORIENTAL
YEAST
CO.,
LTD.
482
TAKABIO
482
TOYOBO
CO.,
LTD.
482
OUTLOOK
483
REFERENCES
484 |
| any_adam_object | 1 |
| any_adam_object_boolean | 1 |
| author2 | Gonzalo, Gonzalo de Lavandera, Iván |
| author2_role | edt edt |
| author2_variant | g d g gd gdg i l il |
| author_GND | (DE-588)1149719907 (DE-588)1235178722 (DE-588)134010639 |
| author_facet | Gonzalo, Gonzalo de Lavandera, Iván |
| building | Verbundindex |
| bvnumber | BV047925586 |
| classification_rvk | VK 5580 VK 8700 VN 7280 |
| ctrlnum | (OCoLC)1289787215 (DE-599)DNB1217132295 |
| dewey-full | 660.63 |
| dewey-hundreds | 600 - Technology (Applied sciences) |
| dewey-ones | 660 - Chemical engineering |
| dewey-raw | 660.63 |
| dewey-search | 660.63 |
| dewey-sort | 3660.63 |
| dewey-tens | 660 - Chemical engineering |
| discipline | Chemie / Pharmazie |
| discipline_str_mv | Chemie / Pharmazie |
| format | Book |
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| genre_facet | Aufsatzsammlung |
| id | DE-604.BV047925586 |
| illustrated | Illustrated |
| index_date | 2024-07-03T19:34:19Z |
| indexdate | 2024-07-20T05:49:46Z |
| institution | BVB |
| institution_GND | (DE-588)16179388-5 |
| isbn | 9783527346837 352734683X |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-033307133 |
| oclc_num | 1289787215 |
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| owner | DE-703 DE-19 DE-BY-UBM DE-634 DE-11 |
| owner_facet | DE-703 DE-19 DE-BY-UBM DE-634 DE-11 |
| physical | xviii, 509 Seiten Illustrationen, Diagramme |
| publishDate | 2021 |
| publishDateSearch | 2021 |
| publishDateSort | 2021 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Biocatalysis for practitioners techniques, reactions and applications edited by Gonzalo de Gonzalo, Iván Lavandera Weinheim Wiley-VCH [2021] © 2021 xviii, 509 Seiten Illustrationen, Diagramme txt rdacontent n rdamedia nc rdacarrier Auf dem Cover: "with a foreword by Vicente Gotor" Biotechnologie (DE-588)4069491-4 gnd rswk-swf Biokatalyse (DE-588)4393622-2 gnd rswk-swf Biocatalysis Biochemical Engineering Biochemische Verfahrenstechnik Biokatalyse Chemical Engineering Chemie Chemische Verfahrenstechnik Chemistry Organic Chemistry Organische Chemie CG20: Biochemische Verfahrenstechnik CH41: Biokatalyse CH80: Organische Chemie (DE-588)4143413-4 Aufsatzsammlung gnd-content Biokatalyse (DE-588)4393622-2 s Biotechnologie (DE-588)4069491-4 s DE-604 Gonzalo, Gonzalo de (DE-588)1149719907 edt Lavandera, Iván (DE-588)1235178722 edt Gotor, Vicente (DE-588)134010639 wpr Wiley-VCH (DE-588)16179388-5 pbl Erscheint auch als Online-Ausgabe, PDF 978-3-527-82444-1 Erscheint auch als Online-Ausgabe, EPUB 978-3-527-82445-8 Erscheint auch als Online-Ausgabe, OBOOK 978-3-527-82446-5 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=033307133&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis 1\p dnb 20211214 DE-101 https://d-nb.info/provenance/plan#dnb |
| spellingShingle | Biocatalysis for practitioners techniques, reactions and applications Biotechnologie (DE-588)4069491-4 gnd Biokatalyse (DE-588)4393622-2 gnd |
| subject_GND | (DE-588)4069491-4 (DE-588)4393622-2 (DE-588)4143413-4 |
| title | Biocatalysis for practitioners techniques, reactions and applications |
| title_auth | Biocatalysis for practitioners techniques, reactions and applications |
| title_exact_search | Biocatalysis for practitioners techniques, reactions and applications |
| title_exact_search_txtP | Biocatalysis for practitioners techniques, reactions and applications |
| title_full | Biocatalysis for practitioners techniques, reactions and applications edited by Gonzalo de Gonzalo, Iván Lavandera |
| title_fullStr | Biocatalysis for practitioners techniques, reactions and applications edited by Gonzalo de Gonzalo, Iván Lavandera |
| title_full_unstemmed | Biocatalysis for practitioners techniques, reactions and applications edited by Gonzalo de Gonzalo, Iván Lavandera |
| title_short | Biocatalysis for practitioners |
| title_sort | biocatalysis for practitioners techniques reactions and applications |
| title_sub | techniques, reactions and applications |
| topic | Biotechnologie (DE-588)4069491-4 gnd Biokatalyse (DE-588)4393622-2 gnd |
| topic_facet | Biotechnologie Biokatalyse Aufsatzsammlung |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=033307133&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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