Industrial Biotransformations

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Lipase Candida antarctica 3) Flow scheme OH 4) Process parameters conversion: 55 % yield: 36 % ee: >98 % reactor type: batch residence time: 6–8 h down stream processing: filtration, extraction (water), extraction (ethylacetate), evaporation enzyme supplier: Novo Nordisk company: GlaxoSmithKline plc, U.K. 5) Product application ● The product is used as building block for Trinems, a new class of totally synthetic b-lactam antibiotics containing a tricyclic skeleton (see Scheme 2). Both compounds are in full clinical development. 6) Literature OMe Fig. 3.1.1.3 – 3 OAc OMe EC 3.1.1.3 ● Stead, P., Marley, H., Mahmoudian, M., Webb, G., Noble, D., Ip, Y.T., Piga, E., Rossi, T., Roberts, S., Dawson, M.J. (1996) Efficient procedures for the large-scale preparation of (1S,2S)-trans-2-methoxycyclohexanol, a key chiral intermediate in the synthesis of tricyclic b-lactam antibiotics, Tetrahedron: Asymmetry 7 (8), 2247–2250 OH OMe 303
Lipase Arthrobacter sp. 1) Reaction conditions [1]: 4.16 M, 800 g · L –1 [192.21 g · mol –1 ] pH: 7.0 T: 40 °C medium: two-phase: aqueous / organic reaction type: carboxylic ester hydrolysis catalyst: suspended enzyme enzyme: triacylglycerol acylhydrolase (triacylglycerol lipase) strain: Arthrobacter sp. CAS (enzyme): [9001–62–1] 2) Remarks O (S,R)-1 OAc 1 = acetic acid 2-methyl-4-oxo-3-prop-2-ynyl-cyclopent-2-enyl ester 2 = 4-hydroxy-3-methyl-2-prop-2-ynyl-cyclopent-2-enone Fig. 3.1.1.3 – 1 E EC 3.1.1.3 OH OAc + O Sumitomo Chemical Co. ● Subsequent to the lipase-catalyzed hydrolysis, the cleaved alcohol is sulfonated in the presence of the acylated compound with methanesulfonyl chloride. The hydrolysis of the sulfonated enantiomer in the presence of small amounts of calcium carbonate takes place under inversion of the chiral center as opposed to the hydrolysis of the acylated enantiomer, which is carried out under retention of the chiral center. By this means, an enantiomeric excess of 99.2 % and a very high yield is achieved for the (R)-alcohol: O O Fig. 3.1.1.3 – 2 304 (R)-1 + OH OSO 2CH 3 O O (R)-2 (S)-1 CH3SO2Cl + CaCO3 - HCl + H2O - CH3SO3H O (R)-3 OAc OAc (S)-2 (S)-2 O (S)-1 OH
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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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Page 266 and 267: Oxidase Rhodococcus erythropolis 2
Page 268 and 269: Desaturase Rhodococcus sp. 1) React
Page 270 and 271: Desaturase Rhodococcus sp. 3) Flow
Page 272 and 273: Oxidase Beauveria bassiana 1) React
Page 274 and 275: Oxidase Beauveria bassiana ● The
Page 276 and 277: Cyclodextrin glycosyltransferase Ba
Page 278 and 279: d-Amino acid transaminase Bacillus
Page 280 and 281: d-Amino acid transaminase Bacillus
Page 282 and 283: Transaminase Bacillus megaterium 1)
Page 284 and 285: Lipase Burkholderia plantarii 2 (R,
Page 286 and 287: Lipase Burkholderia plantarii 3) Fl
Page 288 and 289: Lipase Pseudomonas cepacia 1 = cis-
Page 290 and 291: Lipase Pseudomonas cepacia 5) Produ
Page 292 and 293: Lipase Pseudomonas cepacia 2 F 1 =
Page 294 and 295: Lipase Pseudomonas cepacia 6) Liter
Page 296 and 297: Lipase Mucor miehei Fig. 3.1.1.3 -
Page 298 and 299: Lipase Mucor miehei 6) Literature E
Page 300 and 301: Lipase Porcine pancreas 5) Product
Page 302 and 303: Lipase Pseudomonas fluorescens Fig.
Page 304 and 305: Lipase Pseudomonas fluorescens O O
Page 306 and 307: Lipase Candida cylindracea ● In c
Page 308 and 309: Lipase Candida antarctica 2 F 1) Re
Page 310 and 311: Lipase Candida antarctica ● It sh
Page 312 and 313: Lipase Candida antarctica ● The p
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Page 318 and 319: Lipase Serratia marescens MeO R MeO
Page 320 and 321: Lipase Serratia marescens Fig. 3.1.
Page 322 and 323: Lipase Pseudomonas cepacia 1) React
Page 324 and 325: Lipase Candida antarctica 1) Reacti
Page 326 and 327: Lipase Candida antarctica 4) Proces
Page 328 and 329: -Galactosidase Saccharomyces lactis
Page 330 and 331: Lipase Pseudomonas cepacia ● The
Page 332 and 333: Lactonase Fusarium oxysporum 1 = pa
Page 334 and 335: Lactonase Fusarium oxysporum Fig. 3
Page 336 and 337: Lactonase Fusarium oxysporum 5) Pro
Page 338 and 339: Glutaryl amidase Escherichia coli F
Page 340 and 341: Glutaryl amidase Escherichia coli 6
Page 342 and 343: Glutaryl amidase Pseudomonas sp. 3)
Page 344 and 345: a-Amylase / Amyloglucosidase Bacill
Page 346 and 347: Nucleosidase / Phosphorylase Erwini
Page 348 and 349: Aminopeptidase Pseudomonas putida 1
Page 350 and 351: Aminopeptidase Pseudomonas putida
Page 352 and 353: Aminopeptidase Pseudomonas putida 3
Page 354 and 355: Aminopeptidase Pseudomonas putida
Page 356 and 357: Carboxypeptidase B Pig Pancreas 3)
Page 362 and 363: Trypsin Pig Pancreas 2) Remarks ●
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Trypsin Pig Pancreas 2) Remarks ●
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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
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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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