Industrial Biotransformations

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554 Index of product product enzyme name EC number company page methyl-1,2-epoxyalkanes; (R)-2- Monooxygenase 1.14.14.1 Nippon Mining Holdings, Inc., Japan methylamino-1-phenyl-1propanyl,(+)-threo-2methylenedioxyphenyl)-2propanol;(S)-4-(3,4methylpyrazine-2-carboxylic acid; 5- Pyruvate decarboxylase 4.1.1.1 Krebs Biochemicals & Industries Ltd., India 447 Dehydrogenase 1.1.1.1 Eli Lilly & Co., USA 164 Monooxygenase 1.14.13.X Lonza AG, Switzerland 238 metoprolol Lipase 3.1.1.3 DSM, The Netherlands 288 Oxidase 1.14.X.X DSM, The Netherlands 251 miglitol (1,5.didesoxy-1,5- (2-hydroxyethylimino)-dgluctiol;N-(2-hydroxyethyl)-1desoxynojirimycin) d-Sorbitol dehydrogenase 1.1.99.21 Bayer AG, Germany 182 MPGM = 3-(4methoxyphenyl)glycidic acid methyl ester Lipase 3.1.1.3 Tanabe Seiyaku Co. Ltd., Japan muconic acid; cis,cis- Oxygenase 1.13.11.1 Mitsubishi Chemical Corporation, Japan 219 naphthylalanine, l-2- Aminoacylase 3.5.1.14 Celltech Group plc, U.K. 403 neopentylglycine; l- Leucine dehydrogenase 1.4.1.9 Degussa AG, Germany 203 Neu5Ac N-Acetyl-d-neuraminic acid aldolase 4.1.3.3 GlaxoSmithKline, U.K. 457 Neu5Ac = N-acetylneuraminic acid N-Acetyl-d-neuraminic acid aldolase 4.1.3.3 Forschungszentrum Jülich GmbH, Germany Marukin Shoyu Co., Ltd., Japan nicotinamide Nitrile hydratase 4.2.1.84 Lonza AG, Switzerland 480 norleucine; l- Aminoacylase 3.5.1.14 Degussa AG, Germany 407 norvaline; l- Aminoacylase 3.5.1.14 Degussa AG, Germany 407 O 2 Catalase 1.11.1.6 Novartis, Switzerland 217 oxabicyclo[3.3.0]oct-6-en-3-one; (–)-(1S,5R)-2oxabicyclo[3.3.0]oct-6-en-2-one; (–)-(1R,5S)-3- Cyclohexanone monooxygenase Cyclohexanone monooxygenase 245 306 459 459 1.14.13.22 Sigma Aldrich, USA 227 1.14.13.22 Sigma Aldrich, USA 227 oxygen Catalase 1.11.1.6 Novartis, Switzerland 217 Paclitaxel Lipase 3.1.1.3 Bristol-Myers Squibb, USA 277 palatinose a-Glucosyl transferase 5.4.99.11 Mitsui Seito Co., Ltd., Japan 512 Südzucker AG, Germany 512 pantoic acid; d- Lactonase 3.1.1.25 Fuji Chemicals Industries Co., Ltd., Japan 321 pantolactone; d- Lactonase 3.1.1.25 Fuji Chemicals Industries Co., Ltd., Japan 321 pentafluorostyrene oxide; (R)- Monooxygenase 1.14.14.1 Nippon Mining Holdings, Inc., Japan 245
product enzyme name EC number Index of product company page phenoxybenzaldehyde cyanohydrin; (S)-m- Oxynitrilase 4.1.2.39 DSM, The Netherlands 455 phenoxy-1-isopropylamino-2propanol; (–)-3- Oxidase 1.14.X.X DSM, The Netherlands 251 phenylacetic acid Penicillin amidase 3.5.1.11 Asahi Kasei Chemical Corporation, Japan 391 Dr. Vig. Medicaments, India 386 Unifar, Turkey 388 phenylacetylcarbinol Pyruvate decarboxylase 4.1.1.1 Krebs Biochemicals & Industries Ltd., India 447 phenylalanine; d- d-Amino acid transaminase 2.6.1.21 NSC Technologies, USA 267 phenylalanine; l- Aminoacylase 3.5.1.14 Degussa AG, Germany 407 l-Phenylalanine ammonialyase 4.3.1.5 Genex Corporation, USA 502 phenylalanine; (S)- Subtilisin 3.4.21.62 Coca-Cola, USA 357 phenylcatechol; 3- Oxygenase 1.14.13.44 Sigma Aldrich, USA 230 phenylethylamine; (S)-1- Lipase 3.1.1.3 BASF AG, Germany 273 phenylethyl; (R)-1- Lipase 3.1.1.3 BASF AG, Germany 273 phenylglycine; d-(–)- Penicillin acylase 3.5.1.11 DSM, The Netherlands 397 phenyl-2-propanol; (S)-1- Alcohol dehydrogenase 1.1.1.1 Forschungszentrum Jülich GmbH, Germany 157 picolinic acid Nitrilase / Hydroxylase 3.5.5.1 / 1.5.1.13 Lonza AG, Switzerland 433 pindolol Lipase 3.1.1.3 DSM, The Netherlands 288 piperazine-2-carboxylic acid Amidase 3.5.1.4 Lonza AG, Switzerland 379 propranolol Lipase 3.1.1.3 DSM, The Netherlands 288 propylcatechol; 3- Oxygenase 1.14.13.44 Sigma Aldrich, USA 230 pseudoephedrine, d- Pyruvate decarboxylase 4.1.1.1 Krebs Biochemicals & Industries Ltd., India 447 pyrazine-2-carboxylic acid Nitrilase / Hydroxylase 3.5.5.1 / 1.5.1.13 Lonza AG, Switzerland 430 pyridylalanine, l-2- Aminoacylase 3.5.1.14 Celltech Group plc, U.K. 403 quinapril Aminopeptidase 3.4.11.1 DSM, Netherlands 337 quinoxalinecarboxylic acid; 2- Monooxygenases / Aryl alcohol dehydrogenase / Benzaldehyde dehydrogenase 1.14.13.62 / Pfizer Inc., USA 233 1.1.1.90 / 1.2.1.28 ramipril Aminopeptidase 3.4.11.1 DSM, The Netherlands 337 remikiren Subtilisin 3.4.21.62 Hoffmann La-Roche AG, Switzerland 364 Ribavirin Nucleosidase 3.2.2.1 Yamasa Corporation, Japan 335 Nucleosidase / 3.2.2.1/ Yamasa Corporation, Japan 335 Phosphorylase 2.4.2.2 ribono-c-lactone; d- Lactonase 3.1.1.25 Fuji Chemicals Industries Co., Ltd., Japan 321 555
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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)
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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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