Industrial Biotransformations

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Dehalogenase Pseudomonas putida 5) Product application ● Applications include the synthesis of other optically active compounds such as pharmaceuticals. ● The main application of (S)-2-chloropropionic acid is in the synthesis of optically active phenoxypropionic acid herbicides: Fig. 3.8.1.2 – 3 Cl Cl O COOH Cl O COOH EC 3.8.1.2 ● Many of these herbicides were sold as racemates but because of environmental considerations, the switch to the active enantiomer is preferred, thereby doubling capacities in existing plants and leading to cost reduction through raw material savings. ● Other chiral products synthesized by this dehalogenase technique are shown in the following figure: Cl COOH dichlorprop CH3 N F3C O O COOH Cl Br O N COOH fluazifop mecoprop O O COOH fenoxaprop OH COOH (S)-2-chloropropionic acid (S)-2-bromopropionic acid (S)-lactic acid Br OH COOH (S)-3-bromo-2-hydroxy-propionic acid Fig. 3.8.1.2 – 4 Br COOH Br OH Br COOH COOH (S)-2,3-dibromo-propionic acid (S)-2-bromo-butyric acid (S)-2-hydroxy-butyric acid 437
Dehalogenase Pseudomonas putida 6) Literature EC 3.8.1.2 ● Barth, P.T., Bolton, L., Thomson, J.C. (1992) Cloning and partial sequencing of an operon encoding two Pseudomonas putida haloalkanoate dehalogenases of opposite stereospecificity, J. Bacteriol. 174, 2612–2619 ● Cheetham, P.S.J. (1994) Case studies in applied biocatalysis, in: Applied Biocatalysis (Cabral, J.M.S., Best, D., Boross, L., Tramper, J.; eds.) p. 70 ff., Harwood Academic Publishers, Chur, Switzerland, ● Liddell, J.M., Greer, W. (1990) Biocatalysts, Imperial Chemical Industries PLC, EP 366303 ● Smith, J.M., Harrison, K., Colby, J. (1990) Purification and characterization of d-2-haloacid dehalogenase from Pseudomonas putida strain AJ1/23, J. Gen. Microbiol. 136, 881–886 ● Taylor, S.C. (1988) d-2-Haloalkanoic acid halidohydrolase, Imperial Chemical Industries PLC, US 4758518 ● Taylor, S.C. (1997) (S)-2-Chloropropanoic acid: developments in its industrial manufacture, in: Chirality In Industry II (Collins, A.N., Sheldrake, G.N., Crosby, J., eds.) pp. 207–223, John Wiley & Sons, New York 438
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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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Page 414 and 415: Aminoacylase Aspergillus niger 2 N
Page 416 and 417: Aminoacylase Aspergillus niger 3) F
Page 418 and 419: Aminoacylase Aspergillus oryzae S C
Page 420 and 421: Aminoacylase Aspergillus oryzae 3)
Page 422 and 423: d-Hydantoinase Bacillus brevis Fig.
Page 424 and 425: d-Hydantoinase Bacillus brevis 3) F
Page 426 and 427: Hydantoinase / Carbamoylase Pseudom
Page 428 and 429: l-Hydantoinase Arthrobacter sp. DSM
Page 430 and 431: l-Hydantoinase Arthrobacter sp. DSM
Page 432 and 433: -Lactamase Aureobacterium sp. 3) Fl
Page 434 and 435: -Lactamase Pseudomonas solanacearum
Page 436 and 437: Lactamase / Racemase Cryptococcus l
Page 438 and 439: Nitrilase Acidovorax facilis 1 = 2-
Page 440 and 441: Nitrilase Escherichia coli 1) React
Page 442 and 443: Nitrilase / Hydroxylase Agrobacteri
Page 444 and 445: Nitrilase / Hydroxylase Alcaligenes
Page 446 and 447: Dehalogenase Pseudomonas putida 1)
Page 450 and 451: Haloalkane dehalogenase Alcaligenes
Page 452 and 453: Haloalkane dehalogenase Alcaligenes
Page 454 and 455: Haloalkane dehalogenase Enterobacte
Page 456 and 457: Halohydrin dehalogenase 1 = ethyl-(
Page 458 and 459: Pyruvate decarboxylase Saccharomyce
Page 460 and 461: Acetolactate decarboxylase Bacillus
Page 462 and 463: Aspartate b-decarboxylase Pseudomon
Page 464 and 465: Aspartate b-decarboxylase Pseudomon
Page 466 and 467: Oxynitrilase Hevea brasiliensis 1 =
Page 468 and 469: N-Acetyl-d-neuraminic acid aldolase
Page 470 and 471: N-Acetyl-d-neuraminic acid aldolase
Page 472 and 473: Tyrosine phenol lyase Erwinia herbi
Page 474 and 475: Fumarase Corynebacterium glutamicum
Page 476 and 477: Fumarase Corynebacterium glutamicum
Page 478 and 479: Fumarase Brevibacterium flavum 4) P
Page 480 and 481: Enoyl-CoA hydratase Candida rugosa
Page 482 and 483: Enoyl-CoA hydratase Candida rugosa
Page 484 and 485: Tryptophan synthase Escherichia col
Page 486 and 487: Malease Pseudomonas pseudoalcaligen
Page 488 and 489: Malease Pseudomonas pseudoalcaligen
Page 490 and 491: Nitrile hydratase Pseudomonas chlor
Page 492 and 493: Nitrile hydratase Rhodococcus rhodo
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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
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l-Phenylalanine ammonia-lyase Rhodo
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Amino acid racemase Amycolatopsis o
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GlcNAc 2-epimerase Escherichia coli
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Xylose isomerase Bacillus coagulans
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Xylose isomerase Bacillus coagulans
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a-Glucosyl transferase Protaminobac
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516 7 Quantitative Analysis of Indu
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522 Index of enzyme name enzyme nam
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524 Index of enzyme name enzyme nam
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526 Index of strain strain enzyme n
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532 Index of company company strain
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534 Index of company company strain
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536 Index of starting material star
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546 Index of product product enzyme
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Industrial Biotransformations

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