Industrial Biotransformations

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552 Index of product product enzyme name EC number Hydantoinase / Carbamoylase 3.5.2.4 / 3.5.1.77 hydroxypicolinic acid; 6- Nitrilase / Hydroxylase 3.5.5.1 / 1.5.1.13 hydroxypyrazine-2-carboxylic acid; 5- Nitrilase / Hydroxylase 3.5.5.1 / 1.5.1.13 company page Dr. Vig Medicaments, India 415 Lonza AG, Switzerland 433 Lonza AG, Switzerland 430 hydroxy-2-pyridin-3-yl-ethyl)-2- (4-nitro-phenyl)-acetamide; (R)- N-(2- Dehydrogenase 1.1.X.X Merck & Co., Inc., USA 191 hydroxy-pyridine-3-carboxylate; 6- Nicotinic acid hydroxylase 1.5.1.13 Lonza AG, Switzerland 213 hydroxy-2-(1′,2′,3′,4′-tetrahydro- Reductase 1′,2′,3′,4′-tetrahydro-1′,1′,4′,4′,tetramethyl-6′naphthalenyl)acetate; 2-(R)- 1.1.X.X Bristol-Myers Squibb, USA 197 hydroxy-4-(trimethylamino) butanoate; (R)-3- Carnitine dehydratase 4.2.1.89 Lonza AG, Switzerland 488 ibuprofen, methoxyethyl ester; (R) Lipase 3.1.1.3 Pfizer Inc., USA 294 ibuprofen; (R) Lipase 3.1.1.3 Pfizer Inc., USA 294 indigo Naphthalene dioxygenase 1.13.11.11 Genencor International, Inc., USA 221 indole Naphthalene dioxygenase 1.13.11.11 Genencor International, Inc., USA 221 indole-2,3-dihydrodiol; cis- Naphthalene dioxygenase 1.13.11.11 Genencor International, Inc., USA 221 indole-3-ol; 1H- Naphthalene dioxygenase 1.13.11.11 Genencor International, Inc., USA 221 indoxyl Naphthalene dioxygenase 1.13.11.11 Genencor International, Inc., USA 221 insulin, di-arg- Trypsin 3.4.21.4 Eli Lilly, USA 350 Sanofi Aventis, France 352 insulin, human Carboxypeptidase B 3.4.17.2 Eli Lilly, USA 344 Sanofi Aventis, France 346 Trypsin 3.4.21.4 Novo Nordisk, Denmark 354 insulin, mono-arg- Trypsin 3.4.21.4 Eli Lilly, USA 350 Sanofi Aventis, France 352 insulin, threonin ester Trypsin 3.4.21.4 Novo Nordisk, Denmark 354 isoephedrine Pyruvate decarboxylase 4.1.1.1 Krebs Biochemicals & Industries Ltd., India 447 isomaltulose a-Glucosyl transferase 5.4.99.11 Mitsui Seito Co., Ltd., Japan 512 Südzucker AG, Germany 512 isopropyl-cis-D6-hexadecanoate Desaturase 1.X.X.X Kao Corp., Japan 257 isopropylideneglyceric acid; (R)- Oxidase 1.X.X.X International Bio Synthetics, Inc., The Netherlands 255
product enzyme name EC number Index of product company page isopropylideneglycerol; (R)- Oxidase 1.X.X.X International Bio Synthetics, Inc., The Netherlands 255 isopropyl palmitate Lipase 3.1.1.3 UNICHEMA Chemie BV, The Netherlands 313 isoprpoyl myristate Lipase 3.1.1.3 UNICHEMA Chemie BV, The Netherlands 313 ketoadipinyl-7aminocephalosporanic acid; ad-Aminoacid oxidase 1.4.3.3 Sandoz AG, Switzerland 209 2-keto-6-hydroxyhexanoic acid / d-Amino acid oxidase l-6-hydroxynorleucine 1.4.3.3 Bristol-Myers Squibb, USA 211 lactic acid; (S)- Dehalogenase 3.8.1.2 Astra Zeneca, U.K. 435 leucine; d- d-Amino acid transaminase 2.6.1.21 NSC Technologies, USA 267 leucine; l- Aminoacylase 3.5.1.14 Degussa AG, Germany 407 leucine; l-tert- Leucine dehydrogenase 1.4.1.9 Degussa AG, Germany 203 lisinopril Aminopeptidase 3.4.11.1 DSM, The Netherlands 337 low lactose milk b-Galactosidase 3.2.1.23 Central del Latte, Italy 316 Snow Brand Milk Products Co., Ltd., Japan 316 Sumitomo Chemical Co., Japan 316 lysine; l- Lactamase 3.5.2.11 Toray Industries Inc., Japan 424 Racemase 5.1.1.15 Toray Industries Inc., Japan 424 malate, l- Fumarase 4.2.1.2 Amino GmbH, Germany 463 malate, calcium Fumarase 4.2.1.2 Amino GmbH, Germany 463 malic acid Fumarase 4.2.1.2 Amino GmbH, Germany 463 malic acid; d- Malease 4.2.1.31 DSM, The Netherlands 474 mailc acid; l- Fumarase 4.2.1.2 Tanabe Seiyaku Co., Japan 466 malic acid; (R)- Malease 4.2.1.31 DSM, The Netherlands 474 malic acid; (S)- Fumarase 4.2.1.2 Tanabe Seiyaku Co., Japan 466 mandelic acid; (R)- Nitrilase 3.5.5.1 BASF AG, Germany 429 ManNAc = N-acetyl-dmannosamine GlcNAc 2-epimerase 5.1.3.8 Marukin Shoyu Co., Ltd., Japan mannono-c-lactone; l- Lactonase 3.1.1.25 Fuji Chemicals Industries Co., Ltd., Japan 321 methionine; l- Aminoacylase 3.5.1.14 Degussa AG, Germany 407 methoxycyclohexanol; (+)- (1S,2S)-2- Lipase 3.1.1.3 GlaxoSmithKline, U.K. 302 methoxyisopropylamine; (S)- Transaminase 2.6.1.X Celgene Corporation, USA 271 methoxyphenyl)glycidic acid; 3-(4methoxyphenyl)glycidic acid methyl ester; trans-(2R,3S)-(4methyl4-chloro-4hydroxybutyrate; (R)- 553 Lipase 3.1.1.3 Tanabe Seiyaku Co. Ltd., Japan 306 Lipase 3.1.1.3 Tanabe Seiyaku Co. Ltd., Japan 306 Haloalkane dehalogenase 3.8.1.5 Daiso Co. Ltd., Japan 443 506
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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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Aspartase Escherichia coli 5) Produ
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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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