Industrial Biotransformations

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Carnitine dehydratase Escherichia coli AgOOC OH OH OH OH HOOC COOAg + N Cl COOH + O 2 + 2 (+)-L-1 (D,L)-2 (+)-L-3 1 = silver tartrate 2 = (3-chloro-2-hydroxypropyl)-trimethylammonium salt 3 = tartaric acid 4 = epichlorohydrin 5 = tartrate 6 = (3-cyano-2-hydroxypropyl)-trimethylammonium salt 7 = carnitine Fig. 4.2.1.89 – 3 - 2 AgCl - OOC - OOC OH OH OH OH COO - COO - N + Cl- N + D,L-5 L-5 N + N + (R)-(-)-1 OH OH OH Cl recrystallization 33.2 % yield OH OH L-7 Ca(CN) 2 CN COO - Cl acidic alcoholysis 2 2 (D,L)-4 EC 4.2.1.89 Cl + 2 NMe3 491
Carnitine dehydratase Escherichia coli 3) Flow scheme + H3N COO - + H3N COO - OH Fig. 4.2.1.89 – 4 4) Process parameters conversion: > 99.5 % yield: 99.5 % selectivity: very high (only 3-dehydrocarnitine is accepted for transformation to l-carnitine) ee: 99.9 % chemical purity: 99.8 % reactor type: fed batch reactor volume: 50,000 L capacity: 300 t · a –1 space-time-yield: > 130 g · L –1 ·d –1 down stream processing: cross-flow filtration, ion exchange, crystallization start-up date: 1993 production site: Czech Republic company: Lonza AG, Switzerland 5) Product application E C/N-source cells recrystallization electrodialysis recrystallization EC 4.2.1.89 drying ● l-Carnitine is used as a thyroid inhibitor and in infant foods, health sport and geriatric nutrition. ● The physiological functions are: Transport of long-chain fatty acids through the mitrochondrial membrane and their oxidation play an important role in energy metabolism. It is involved in regulating the level of blood lipids. l-Carnitine is utilized as a drug to increase cardiac output, improve myocardial function and treat cartinine deficiency (especially after hemodialysis). 492 active carbon
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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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Page 454 and 455: Haloalkane dehalogenase Enterobacte
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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
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Page 490 and 491: Nitrile hydratase Pseudomonas chlor
Page 492 and 493: Nitrile hydratase Rhodococcus rhodo
Page 500 and 501: Carnitine dehydratase Escherichia c
Page 504 and 505: Carnitine dehydratase Escherichia c
Page 506 and 507: 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
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542 Index of starting material star
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544 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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