Industrial Biotransformations

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548 Index of product product enzyme name EC number company page bis(4-fluorophenyl])-3-(1methyl-1H-tetrazol-5-yl)-1,3butadienyl]-tetra-hydro-4hydroxy-2H-pyran-2-one; [4R- [4a,6b(E)]]-6-[4,4- Lipase 3.1.1.3 Bristol-Myers Squibb, USA 281 boc-l-3-(4-thiazolyl)alanine; N- = Boc-Taz Aminoacylase 3.5.1.14 Celltech Group plc, U.K. 403 Boc-Taz = N-boc-l-3-(4thiazolyl)alanine Aminoacylase 3.5.1.14 Celltech Group plc, U.K. 403 bromocatechol; 3- Oxygenase 1.14.13.44 Sigma Aldrich, USA 230 butanedioic acid 4-ethyl ester; (R)-(2-methylpropyl)- Subtilisin 3.4.21.62 Hoffmann La-Roche AG, Switzerland butylcatechol; 3-sec- Oxygenase 1.14.13.44 Sigma Aldrich, USA 230 carazolol Lipase 3.1.1.3 DSM, The Netherlands 288 carbamoyl-d-hydroxyphenyl glycine; d-Ncarbamoyl-d-phenylglycine; d- N- Hydantoinase / Carbamoylase 3.5.2.4 / 3.5.1.77 367 Dr. Vig Medicaments, India 415 d-Hydantoinase 3.5.2.2 Kanegafuchi Chemical Industries Co., Ltd., Japan carnitine; l- Carnitine dehydratase 4.2.1.89 Lonza AG, Switzerland 488 catechol Oxygenase 1.13.11.1 Mitsubishi Chemical Corporation, Japan 219 cefaclor Penicillin acylase 3.5.1.11 DSM, The Netherlands 397 cefadroxil Penicillin acylase 3.5.1.11 DSM, The Netherlands 397 cefalexin Penicillin acylase 3.5.1.11 DSM, The Netherlands 397 chloro-2,3-epoxypropane; 1- Haloalkane dehalogenase 3.8.1.5 Daiso Co. Ltd., Japan 439 chloro-3-hydroxy-butanoate; (S)-4- Carbonyl reductase 1.1.1.1 Kaneka Corporation, Japan 172 chloro-3-hydroxybutanoic acid methyl ester; (S)-4- Dehydrogenase 1.1.X.X Bristol-Myers Squibb, USA 187 chlorocatechol; 3- Oxygenase 1.14.13.44 Sigma Aldrich, USA 230 chloropropionic acid; (S)- Dehalogenase 3.8.1.2 Astra Zeneca, U.K. 435 cilazapril Aminopeptidase 3.4.11.1 DSM, Netherlands 337 cyanophenylalanine, l-4- Aminoacylase 3.5.1.14 Celltech Group plc, U.K. 403 cyanovaleramide; 5- Nitrile hydratase 4.2.1.84 DuPont, USA 478 cyclodextrin; a- Cyclodextrin glycosyltransferase 2.4.1.19 Mercian Co., Ltd., Japan 264 cyclodextrin; b- Cyclodextrin glycosyltransferase 2.4.1.19 Mercian Co., Ltd., Japan 264 cyclodextrin; c- Cyclodextrin glycosyltransferase 2.4.1.19 Mercian Co., Ltd., Japan 264 delapril Aminopeptidase 3.4.11.1 DSM, The Netherlands 337 deoxy-6-butylaminosorbose; 6- d-Sorbitol dehydrogenase 1.1.99.21 Pfizer Inc., USA 185 desoxynojirimycin; 1- d-Sorbitol dehydrogenase 1.1.99.21 Bayer AG, Germany 182 diepoxydecane; (R,R)-1,2,9,10- Monooxygenase 1.14.14.1 Nippon Mining Holdings, Inc., Japan 245 411
product enzyme name EC number dihydro-(4S)-hydroxy-(6S)methyl-4Hthieno[2,3b]thiopyran-7,7dioxide; 5,6- Index of product company page Alcohol dehydrogenase 1.1.1.1 Zeneca Life Science Molecules, U.K. dihydroxy-biphenyl; 2,3- Oxygenase 1.14.13.44 Sigma Aldrich, USA 230 dihydroxycatechol; 1,2- Benzoate dioxygenase 1.14.12.10 ICI, U.K. 225 dihydroxy-cyclohexa-2,4dienecarboxylic acid; 1,6dihydroxyphenylalanine; l-3,4- (= l-dopa) Oxygenase 1.13.11.1 Mitsubishi Chemical Corporation, Japan 219 Tyrosine phenol lyase 4.1.99.2 Ajinomoto Co., Japan 461 Diltiazem Lipase 3.1.1.3 Tanabe Seiyaku Co. Ltd., Japan diltiazem Naphthalene dioxygenase 1.13.11.11 Genencor International, Inc., USA dimethyl-1,3-dioxolane-4carboxylic acid; (R)-2,2dimethyl-1,3-dioxolane-4methanol; (R)-2,2- Oxidase 1.X.X.X International Bio Synthetics, Inc., The Netherlands Oxidase 1.X.X.X International Bio Synthetics, Inc., The Netherlands dimethylbutyl glycine; l-5,5- Leucine dehydrogenase 1.4.1.9 Degussa AG, Germany 203 dimethylcyclopropanecarboxamide; (S)-(+)-2,2- Amidase 3.5.1.4 Lonza AG, Switzerland 377 dimethylpropane glycine; l-3,3- Leucine dehydrogenase 1.4.1.9 Degussa AG, Germany 203 dinitrodibenzyl (DNDB) Catalase 1.11.1.6 Novartis, Switzerland 217 dopa; l-(=l-3,4dihydroxyphenylalanine) Tyrosine phenol lyase 4.1.99.2 Ajinomoto Co., Japan 461 enalapril Aminopeptidase 3.4.11.1 DSM, The Netherlands 337 ephedrine, l- Pyruvate decarboxylase 4.1.1.1 Krebs Biochemicals & Industries Ltd., India 447 epichlorohydrin Haloalkane dehalogenase 3.8.1.5 Daiso Co. Ltd., Japan 439 epoxide; 1,2- Monooxygenase 1.14.14.1 Nippon Mining Holdings, Inc., Japan 245 epoxyalkanes; (R)-1,2- Monooxygenase 1.14.14.1 Nippon Mining Holdings, Inc., Japan 245 epoxydec-9-ene; (R)-1,2- Monooxygenase 1.14.14.1 Nippon Mining Holdings, Inc., Japan 245 erythrono-c-lactone; d- Lactonase 3.1.1.25 Fuji Chemicals Industries Co., Ltd., Japan 321 ethoxycarbonyl-3,6-dihydro- 2H-pyran; (S)-2- Subtilisin 3.4.21.62 PGG Industries, USA 371 ethyl-3-amino-4-pentynoate; (S)- Penicillin amidase 3.5.1.11 Pfizer Inc., USA 395 ethyl-3-hydroxybutyrate; (R)- Alcohol dehydrogenase 1.1.1.1 Wacker Chemie, Germany 170 ethyl-3-methylpropane glycine, l-3- Leucine dehydrogenase 1.4.1.9 Degussa AG, Germany 203 ethyl-5-(S)-hydroxyhexanoate Reductase 1.1.X.X Bristol-Myers Squibb, USA 195 549 153 306 221 255 255
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Industrial Biotransformations Edite
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Industrial Biotransformations Secon
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Contents Preface to the first editi
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5 Basics of Bioreaction Engineering
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X Preface to the first edition many
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XII Preface to the second edition E
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XIV List of Contributors Prof. Dr.
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2 1 History of Industrial Biotransf
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10 1 History of Industrial Biotrans
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R' 16 O H N 1 History of Industrial
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38 2 The Enzyme Classification Tab.
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40 2 The Enzyme Classification trib
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42 2 The Enzyme Classification EC 1
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54 2 The Enzyme Classification 2.2.
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56 2 The Enzyme Classification The
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60 2 The Enzyme Classification in g
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62 2 The Enzyme Classification Refe
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64 3 Retrosynthetic Biocatalysis 3.
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66 3 Retrosynthetic Biocatalysis R
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76 3 Retrosynthetic Biocatalysis R
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78 3 Retrosynthetic Biocatalysis Wh
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88 3 Retrosynthetic Biocatalysis Re
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90 3 Retrosynthetic Biocatalysis (D
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4 Optimization of Industrial Enzyme
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4.2 Learning from Nature Nature its
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4.3 Enzyme Production Using Bacteri
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4.4 Improvements to Enzymes by Mole
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1 4.4 Improvements to Enzymes by Mo
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4.4 Improvements to Enzymes by Mole
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4.5 Identification of Improved Enzy
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4.5 Identification of Improved Enzy
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Galleron, N., Ghim, S.Y., Glaser, P
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ment, Relaxation, and Reversal of t
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81 Goddard, J.-P., Reymond, J.-L. 2
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5 Basics of Bioreaction Engineering
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where r p = selectivity to componen
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5.1 Definitions operoxidase (CPO) h
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5.1 Definitions The residence time
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5.1 Definitions In iso-electric pre
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5.2 Biocatalyst Kinetics formation
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5.2 Biocatalyst Kinetics K M values
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v ˆ V max ‰SŠ KM 1‡ ‰PŠ KI
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5.3 Basic Reactor Types and their M
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dx concentration [S] 0 [S] 1 [S] e
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5.4 Biocatalyst Recycling and Recov
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. better stability, especially towa
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5.4.2 Cross-linking 5.4 Biocatalyst
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. immobilization methods . substrat
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References Owing to the need for st
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40 Vuorilehto, K., Lütz, S., Wandr
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Common name of enzyme Name of strai
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Common name of enzyme Name of strai
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Alcohol dehydrogenase Neurospora cr
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Alcohol dehydrogenase Neurospora cr
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Alcohol dehydrogenase Rhodococcus e
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Alcohol dehydrogenase Rhodococcus e
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Alcohol dehydrogenase Acinetobacter
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Alcohol dehydrogenase Acinetobacter
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Dehydrogenase Zygosaccharomyces rou
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Alcohol dehydrogenase Lactobacillus
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Carbonyl reductase Escherichia coli
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Aldehyde reductase Escherichia coli
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Lactate dehydrogenase Staphylococcu
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d-Lactate dehydrogenase Leuconostoc
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d-Lactate dehydrogenase Leuconostoc
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d-Sorbitol dehydrogenase Gluconobac
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d-Sorbitol dehydrogenase Gluconobac
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Dehydrogenase Geotrichum candidum 1
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Ketoreductase 1 = ethyl-4-chloro-3-
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Dehydrogenase Candida sorbophila N
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Dehydrogenase Candida sorbophila N
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Reductase Pichia methanolica 1 = Et
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Reductase Aureobasidium pullulans S
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Reductase Nocardia salmonicolor SC
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Glutamate dehydrogenase / Glucose 1
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Leucine dehydrogenase Bacillus spha
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Leucine dehydrogenase Bacillus spha
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Phenylalanine dehydrogenase / Forma
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d-Aminoacid oxidase Trijonopsis var
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d-Amino acid oxidase Trigonopsis va
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Nicotinic acid hydroxylase Achromob
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Nicotinic acid hydroxylase Achromob
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Catalase Microbial source 1) Reacti
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Oxygenase Arthrobacter sp. 1) React
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Naphthalene dioxygenase Pseudomonas
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Naphthalene dioxygenase Pseudomonas
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Benzoate dioxygenase Pseudomonas pu
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Cyclohexanone monooxygenase Acineto
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Cyclohexanone monooxygenase Acineto
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Oxygenase Escherichia coli OH OH 1
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Monooxygenases / Aryl alcohol dehyd
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Styrene monooxygenase Escherichia c
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Styrene monooxygenase Escherichia c
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Monooxygenase Pseudomonas putida H
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Monooxygenase Streptomyces sp. SC 1
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Oxygenase Nocardia autotropica 1) R
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Monooxygenase Nocardia corallina 1
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Monooxygenase Nocardia corallina
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Monooxygenase Nocardia corallina O
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Oxidase Pseudomonas oleovorans 1) R
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Reductase Baker’s yeast 1 = oxois
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Oxidase Rhodococcus erythropolis 2
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Desaturase Rhodococcus sp. 1) React
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Desaturase Rhodococcus sp. 3) Flow
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Oxidase Beauveria bassiana 1) React
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Oxidase Beauveria bassiana ● The
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Cyclodextrin glycosyltransferase Ba
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d-Amino acid transaminase Bacillus
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d-Amino acid transaminase Bacillus
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Transaminase Bacillus megaterium 1)
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Lipase Burkholderia plantarii 2 (R,
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Lipase Burkholderia plantarii 3) Fl
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Lipase Pseudomonas cepacia 1 = cis-
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Lipase Pseudomonas cepacia 5) Produ
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Lipase Pseudomonas cepacia 2 F 1 =
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Lipase Pseudomonas cepacia 6) Liter
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Lipase Mucor miehei Fig. 3.1.1.3 -
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Lipase Mucor miehei 6) Literature E
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Lipase Porcine pancreas 5) Product
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Lipase Pseudomonas fluorescens Fig.
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Lipase Pseudomonas fluorescens O O
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Lipase Candida cylindracea ● In c
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Lipase Candida antarctica 2 F 1) Re
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Lipase Candida antarctica ● It sh
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Lipase Candida antarctica ● The p
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Lipase Candida antarctica 3) Flow s
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Lipase Arthrobacter sp. ● For thi
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Lipase Serratia marescens MeO R MeO
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Lipase Serratia marescens Fig. 3.1.
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Lipase Pseudomonas cepacia 1) React
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Lipase Candida antarctica 1) Reacti
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Lipase Candida antarctica 4) Proces
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-Galactosidase Saccharomyces lactis
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Lipase Pseudomonas cepacia ● The
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Lactonase Fusarium oxysporum 1 = pa
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Lactonase Fusarium oxysporum Fig. 3
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Lactonase Fusarium oxysporum 5) Pro
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Glutaryl amidase Escherichia coli F
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Glutaryl amidase Escherichia coli 6
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Glutaryl amidase Pseudomonas sp. 3)
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a-Amylase / Amyloglucosidase Bacill
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Nucleosidase / Phosphorylase Erwini
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Aminopeptidase Pseudomonas putida 1
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Aminopeptidase Pseudomonas putida
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Aminopeptidase Pseudomonas putida 3
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Aminopeptidase Pseudomonas putida
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Carboxypeptidase B Pig Pancreas 3)
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Trypsin Pig Pancreas 2) Remarks ●
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Subtilisin Bacillus licheniformis 1
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Subtilisin Bacillus licheniformis
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Subtilisin Bacillus licheniformis
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Subtilisin Bacillus sp. EtOOC (R/S)
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Subtilisin Bacillus sp. drug discov
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Subtilisin Bacillus lentus 1 = (R,S
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Thermolysin Bacillus thermoproteoly
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Thermolysin Bacillus thermoproteoly
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Amidase Comamonas acidovorans 1) Re
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Amidase Klebsiella terrigena 2 H N
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Amidase Klebsiella terrigena 6) Lit
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Amidase Klebsiella oxytoca company:
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Urease Lactobacillus fermentum ●
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Penicillin amidase Escherichia coli
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Penicillin amidase Bacillus megater
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Penicillin acylase Escherichia coli
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Aminoacylase Aspergillus niger 2 N
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Aminoacylase Aspergillus niger 3) F
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Aminoacylase Aspergillus oryzae S C
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Aminoacylase Aspergillus oryzae 3)
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d-Hydantoinase Bacillus brevis Fig.
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d-Hydantoinase Bacillus brevis 3) F
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Hydantoinase / Carbamoylase Pseudom
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l-Hydantoinase Arthrobacter sp. DSM
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l-Hydantoinase Arthrobacter sp. DSM
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-Lactamase Aureobacterium sp. 3) Fl
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-Lactamase Pseudomonas solanacearum
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Lactamase / Racemase Cryptococcus l
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Nitrilase Acidovorax facilis 1 = 2-
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Nitrilase Escherichia coli 1) React
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Nitrilase / Hydroxylase Agrobacteri
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Nitrilase / Hydroxylase Alcaligenes
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Dehalogenase Pseudomonas putida 1)
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Dehalogenase Pseudomonas putida 5)
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Haloalkane dehalogenase Alcaligenes
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Haloalkane dehalogenase Alcaligenes
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Haloalkane dehalogenase Enterobacte
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Halohydrin dehalogenase 1 = ethyl-(
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Pyruvate decarboxylase Saccharomyce
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Acetolactate decarboxylase Bacillus
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Aspartate b-decarboxylase Pseudomon
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Aspartate b-decarboxylase Pseudomon
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Oxynitrilase Hevea brasiliensis 1 =
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N-Acetyl-d-neuraminic acid aldolase
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N-Acetyl-d-neuraminic acid aldolase
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Tyrosine phenol lyase Erwinia herbi
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Fumarase Corynebacterium glutamicum
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Fumarase Corynebacterium glutamicum
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Fumarase Brevibacterium flavum 4) P
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Enoyl-CoA hydratase Candida rugosa
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Enoyl-CoA hydratase Candida rugosa
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Tryptophan synthase Escherichia col
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Malease Pseudomonas pseudoalcaligen
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Malease Pseudomonas pseudoalcaligen
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Nitrile hydratase Pseudomonas chlor
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Nitrile hydratase Rhodococcus rhodo
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Carnitine dehydratase Escherichia c
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Aspartase Escherichia coli 3) Flow
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Page 510 and 511: Aspartase Brevibacterium flavum 3)
Page 512 and 513: l-Aspartase Escherichia coli 3) Flo
Page 514 and 515: l-Phenylalanine ammonia-lyase Rhodo
Page 516 and 517: Amino acid racemase Amycolatopsis o
Page 518 and 519: GlcNAc 2-epimerase Escherichia coli
Page 520 and 521: Xylose isomerase Bacillus coagulans
Page 522 and 523: Xylose isomerase Bacillus coagulans
Page 524 and 525: a-Glucosyl transferase Protaminobac
Page 526 and 527: 516 7 Quantitative Analysis of Indu
Page 532 and 533: 522 Index of enzyme name enzyme nam
Page 534 and 535: 524 Index of enzyme name enzyme nam
Page 536 and 537: 526 Index of strain strain enzyme n
Page 542 and 543: 532 Index of company company strain
Page 544 and 545: 534 Index of company company strain
Page 546 and 547: 536 Index of starting material star
Page 556 and 557: 546 Index of product product enzyme
Page 566: 556 Index of product product enzyme
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Industrial Biotransformations

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