Enhancing productivity for cascade biotransformation of styrene to (S)-vicinal diol with biphasic system in hollow fiber membrane bioreactor

Applied Microbiology and Biotechnology

Volumn 101, Issue 5, 2017, Pages 1857-1868

  Gao, Pengfei ^a   Wu, Shuke ^a   Praveen, Prashant ^a   Loh, Kai Chee ^a   Li, Zhi ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Biocatalysis; Biphasic system; Cascade biotransformation; Hollow fiber membrane bioreactor; Substrate inhibition; Trans dihydroxylation

Indexed keywords

BIOREACTORS; CATALYSIS; CELL CULTURE; EMULSIFICATION; ESCHERICHIA COLI; HYDROXYLATION; ORGANIC SOLVENTS; PRODUCTIVITY; STYRENE; SUBSTRATES; SUSPENSIONS (FLUIDS); TOXICITY;

BIOCATALYSIS; BIPHASIC SYSTEMS; DIHYDROXYLATION; HOLLOW FIBER MEMBRANE BIOREACTOR; SUBSTRATE INHIBITION;

BIOCONVERSION;

CYCLOHEXANE; EPOXIDE HYDROLASE; HEXADECANE; STYRENE; UNSPECIFIC MONOOXYGENASE; ALKANE; ETHYLENE GLYCOL DERIVATIVE; N-HEXADECANE; OXYGENASE; STYRENE GLYCOL; STYRENE MONOOXYGENASE;

AQUEOUS SOLUTION; BIOREACTOR; BIOTRANSFORMATION; CATALYSIS; COLIFORM BACTERIUM; GENE EXPRESSION; INHIBITION; MEMBRANE; ORGANIC COMPOUND; PURIFICATION; TOXICITY;

ARTICLE; BIOREACTOR EQUIPMENT; BIOTRANSFORMATION; CATALYST; CELL DENSITY; CONTROLLED STUDY; DIHYDROXYLATION; EMULSION; ENANTIOSELECTIVITY; ESCHERICHIA COLI; FOAMING; HOLLOW FIBER MEMBRANE BIOREACTOR; MICROBIAL GROWTH; NONHUMAN; PRODUCT RECOVERY; REACTOR CASCADE; TOXICITY; BIOCATALYSIS; BIOREACTOR; CHEMISTRY; ENZYMOLOGY; METABOLISM;

ESCHERICHIA COLI;

ALKANES; BIOCATALYSIS; BIOREACTORS; BIOTRANSFORMATION; EPOXIDE HYDROLASES; ESCHERICHIA COLI; ETHYLENE GLYCOLS; OXYGENASES; STYRENE;

EID: 84994476362     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-016-7954-1     Document Type: Article

References (67)

1. Atsumi S, Cann AF, Connor MR, Shen CR, Smith KM, Brynildsen MP, Chou KJ, Hanai T, Liao JC (2008) Metabolic engineering of Escherichia coli for 1-butanol production. Metabolic Eng 10(6):305–311
2. Brandenbusch C, Bühler B, Hoffmann P, Sadowski G, Schmid A (2010) Efficient phase separation and product recovery in organic-aqueous bioprocessing using supercritical carbon dioxide. Biotech Bioeng 107(4):642–651
3. Breuer M, Ditrich K, Habicher T, Hauer B, Kesseler M, Sturmer R, Zelinski T (2004) Industrial methods for the production of optically active intermediates. Angew Chem Int Ed 43(7):788–824
4. Buchholz K, Kasche V, Bornscheuer UT (2012) Biocatalysts and enzyme technology. Wiley-Blackwell, Hoboken
5. Burton SG (2003) Oxidizing enzymes as biocatalysts. Trends Biotechnol 21(12):543–549
6. Chang D, Heringa MF, Witholt B, Li Z (2003a) Enantioselective trans dihydroxylation of nonactivated C-C double bond of aliphatic heterocycles with Sphingomonas sp. HXN-200. J Org Chem 68(22):8599–8606
7. Chang D, Wang Z, Heringa MF, Wirthner R, Witholt B, Li Z (2003b) Highly enantioselective hydrolysis of alicyclic meso-epoxides with a bacterial epoxide hydrolase from Sphingomonas sp. HXN-200: simple syntheses of alicyclic vicinal transdiols. Chem Commun (8):960–1
8. Collins J, Grund M, Brandenbusch C, Sadowski G, Schmid A, Bühler B (2015) The dynamic influence of cells on the formation of stable emulsions in organic–aqueous biotransformations. J Ind Microbiol Biotechnol 42(7):1011–1026
9. Connors N, Prevoznak R, Chartrain M, Reddy J, Singhvi R, Patel Z, Olewinski R, Salmon P, Wilson J, Greasham R (1997) Conversion of indene to cis-(1S),(2R)-indandiol by mutants of Pseudomonas putida F1. J Ind Microbiol Biotechnol 18(6):353–359
10. Cornmell RJ, Winder CL, Schuler S, Goodacre R, Stephens G (2008) Using a biphasic ionic liquid/water reaction system to improve oxygenase-catalysed biotransformation with whole cells. Green Chem 10(6):685–691
11. Duetz WA, Van Beilen JB, Witholt B (2001) Using proteins in their natural environment: potential and limitations of microbial whole-cell hydroxylations in applied biocatalysis. Curr Opin Biotechnol 12(4):419–425
12. Faber K (1997) Biotransformations in organic chemistry, 3rd edn. Springer, Berlin, pp. 300–308
13. Gao P, Li A, Lee HH, Wang DI, Li Z (2014) Enhancing enantioselectivity and productivity of P450-catalyzed asymmetric sulfoxidation with an aqueous/ionic liquid biphasic system. ACS Catal 4(10):3763–3771
14. Gavrilov KN, Zheglov SV, Gavrilova MN, Chuchelkin IV, Groshkin NN, Rastorguev EA, Davankov VA (2011) Phosphoramidites based on phenyl-substituted 1, 2-diols as ligands in palladium-catalyzed asymmetric allylations: the contribution of steric demand and chiral centers to the enantioselectivity. Tetrahedron Lett 52(43):5706–5710
15. Gong P-F, Xu J-H (2005) Bio-resolution of a chiral epoxide using whole cells of Bacillus megaterium ECU1001 in a biphasic system. Enzyme Microb Tech 36(2):252–257
16. Hack C, Woodley J, Lilly M, Liddell J (2000) Design of a control system for biotransformation of toxic substrates: toluene hydroxylation by Pseudomonas putida UV4. Enzyme Microb Tech 26(7):530–536
17. Halan B, Schmid A, Buehler K (2010) Maximizing the productivity of catalytic biofilms on solid supports in membrane aerated reactors. Biotech Bioeng 106(4):516–527
18. He J-Y, Sun Z-H, Ruan W-Q, Xu Y (2006) Biocatalytic synthesis of ethyl (S)-4-chloro-3-hydroxy-butanoate in an aqueous-organic solvent biphasic system using Aureobasidium pullulans CGMCC 1244. Process Biochem 41(1):244–249
19. Hüsken LE, Oomes M, Schroën K, Tramper J, de Bont JA, Beeftink R (2002) Membrane-facilitated bioproduction of 3-methylcatechol in an octanol/water two-phase system. J Biotechnol 96(3):281–289
20. Jia X, Wang Z, Li Z (2008) Preparation of (S)-2-, 3-, and 4-chlorostyrene oxides with the epoxide hydrolase from Sphingomonas sp. HXN-200. Tetrahedron Asymmetry 19(4):407–415
21. Kansal H, Banerjee UC (2009) Enhancing the biocatalytic potential of carbonyl reductase of Candida viswanathii using aqueous-organic solvent system. Biores Technol 100(3):1041–1047
22. Karabika E, Kallimanis A, Dados A, Pilidis G, Drainas C, Koukkou A (2009) Taxonomic identification and use of free and entrapped cells of a new Mycobacterium sp., strain Spyr1 for degradation of polycyclic aromatic hydrocarbons (PAHs). Appl Biochem Biotech 159(1):155–167
23. Kim J-H, Yang H, Park J, Boons G-J (2005) A general strategy for stereoselective glycosylations. J Am Chem Soc 127(34):12090–12097
24. Ladkau N, Schmid A, Bühler B (2014) The microbial cell—functional unit for energy dependent multistep biocatalysis. Curr Opin Biotechnol 30(4):178–189
25. Lau J, Frykman S, Regentin R, Ou S, Tsuruta H, Licari P (2002) Optimizing the heterologous production of epothilone D in Myxococcus xanthus. Biotech Bioeng 78(3):280–288
26. Li Z, Van Beilen JB, Duetz WA, Schmid A, de Raadt A, Griengl H, Witholt B (2002) Oxidative biotransformations using oxygenases. Curr Opin Chem Biol 6(2):136–144
27. Li A-T, Zhang J-D, Yu H-L, Pan J, Xu J-H (2011) Significantly improved asymmetric oxidation of sulfide with resting cells of Rhodococcus sp. in a biphasic system. Process Biochem 46(3):689–694
28. Li A, Liu J, Pham SQ, Li Z (2013) Engineered P450pyr monooxygenase for asymmetric epoxidation of alkenes with unique and high enantioselectivity. Chem Commun 49(98):11572–11574
29. Liu J, Li Z (2013) Cascade biotransformations via enantioselective reduction, oxidation, and hydrolysis: preparation of (R)-δ-lactones from 2-alkylidenecyclopentanones. ACS Catal 3(5):908–911
30. Liu Z, Michel J, Wang Z, Witholt B, Li Z (2006) Enantioselective hydrolysis of styrene oxide with the epoxide hydrolase of Sphingomonas sp. HXN-200. Tetrahedron Asymmetry 17(1:47–52)
31. Liu J, Wu JC, Li Z (2014) Enoyl acyl carrier protein reductase (FabI) catalyzed asymmetric reduction of the C-C double bond of α,β-unsaturated ketones: preparation of (R)-2-alkyl-cyclopentanones. Chem Commun 50(68):9729–9732
32. Lye G, Woodley J (2000) Advances in the selection and design of two-liquid phase biocatalytic reactors. In: Cabral JMS, Mota M, Tramper J (eds) Multiphase bioreactor design. Taylor and Francis, London, pp. 115–134
33. May SW, Padgette R (1983) Oxidoreductase enzymes in biotechnology: current status and future potential. Nat Biotechnol 1:677–686
34. Mei J, Min H, Lü Z (2009) Enhanced biotransformation of L-phenylalanine to 2-phenylethanol using an in situ product adsorption technique. Process Biochem 44(8):886–890
35. Mirata MA, Heerd D, Schrader J (2009) Integrated bioprocess for the oxidation of limonene to perillic acid with Pseudomonas putida DSM 12264. Process Biochem 44(7):764–771
36. Molinari F, Aragozzini F, Cabral J, Prazeres D (1997) Continuous production of isovaleraldehyde through extractive bioconversion in a hollow-fiber membrane bioreactor. Enzyme Microb Tech 20(8):604–611
37. Muschiol J, Peters C, Oberleitner N, Mihovilovic MD, Bornscheuer UT, Rudroff F (2015) Cascade catalysis—strategies and challenges en route to preparative synthetic biology. Chem Commun 51:5798–5811
38. Pandey RK, Fernandes RA, Kumar P (2002) An asymmetric dihydroxylation route to enantiomerically pure norfluoxetine and fluoxetine. Tetrahedron Lett 43(25):4425–4426
39. Panke S, Held M, Wubbolts M (2004) Trends and innovations in industrial biocatalysis for the production of fine chemicals. Curr Opin Biotech 15(4):272–279
40. Park JB, Bühler B, Habicher T, Hauer B, Panke S, Witholt B, Schmid A (2006) The efficiency of recombinant Escherichia coli as biocatalyst for stereospecific epoxidation. Biotechnol Bioeng 95(3):501–512
41. Park SW, Han SJ, Kim D-S, Sim SJ (2007) Improvement of epothilone B production by in situ removal of ammonium using cation exchange resin in Sorangium cellulosum culture. Biochem Eng J 37(3):328–331
42. Peschel A, Otto M, Jack RW, Kalbacher H, Jung G, Götz F (1999) Inactivation of the dlt operon in Staphylococcus aureus confers sensitivity to defensins, protegrins, and other antimicrobial peptides. J Biol Chem 274(13):8405–8410
43. Pfruender H, Amidjojo M, Kragl U, Weuster-Botz D (2004) Efficient whole-cell biotransformation in a biphasic ionic liquid/water system. Angew Chem Int Ed 43(34):4529–4531
44. Praveen P, Loh K-C (2012) Two-phase biodegradation of phenol in a hollow fiber membrane bioreactor. J Environ Eng 139(5):654–660
45. Praveen P, Loh K-C (2013a) Simultaneous extraction and biodegradation of phenol in a hollow fiber supported liquid membrane bioreactor. J Membrane Sci 430:242–251
46. Praveen P, Loh K-C (2013b) Two-phase biodegradation of phenol in trioctylphosphine oxide impregnated hollow fiber membrane bioreactor. Biochem Eng J 79:274–282
47. Praveen P, Loh K-C (2014) Kinetics modeling of two phase biodegradation in a hollow fiber membrane bioreactor. Sep Purif Technol 122:350–358
48. Raghavan S, Rathore K (2009) Asymmetric synthesis of (−)-tetrahydrolipstatin. Tetrahedron 65(48):10083–10092
49. Reetz MT, Zonta A, Schimossek K, Jaeger KE, Liebeton K (1997) Creation of enantioselective biocatalysts for organic chemistry by in vitro evolution. Angew Chem Int Ed 36(24):2830–2832
50. Roddick FA, Britz ML (1997) Production of hexanoic acid by free and immobilised cells of Megasphaera elsdenii: influence of in-situ product removal using ion exchange resin. J Chem Technol Biot 69(3):383–391
51. Schrewe M, Julsing MK, Bühler B, Schmid A (2013) Whole-cell biocatalysis for selective and productive C–O functional group introduction and modification. Chem Soc Rev 42(15):6346–6377
52. Urlacher VB, Eiben S (2006) Cytochrome P450 monooxygenases: perspectives for synthetic application. Trends Biotechnol 24(7):324–330
53. Urlacher VB, Girhard M (2012) Cytochrome P450 monooxygenases: an update on perspectives for synthetic application. Trends Biotechnol 30(1):26–36
54. Wang H, Dong Q, Meng C, Shi XA, Guo Y (2011) A continuous and adsorptive bioprocess for efficient production of the natural aroma chemical 2-phenylethanol with yeast. Enzyme Microb Tech 48(4):404–407
55. Wojaczynska E, Wojaczynski J (2010) Enantioselective synthesis of sulfoxides: 2000–2009. Chem Rev 110(7):4303–4356
56. Wu S, Li A, Chin YS, Li Z (2013) Enantioselective hydrolysis of racemic and meso-epoxides with recombinant Escherichia coli expressing epoxide hydrolase from Sphingomonas sp. HXN-200: preparation of epoxides and vicinal diols in high ee and high concentration. ACS Catal 3(4):752–759
57. Wu S, Chen Y, Xu Y, Li A, Xu Q, Glieder A, Li Z (2014) Enantioselective trans-dihydroxylation of aryl olefins by cascade biocatalysis with recombinant Escherichia coli coexpressing monooxygenase and epoxide hydrolase. ACS Catal 4(2):409–420
58. Wu S, Zhou Y, Wang T, Too H-P, Wang DI, Li Z (2016a) Highly regio-and enantioselective multiple oxy-and amino-functionalizations of alkenes by modular cascade biocatalysis. Nat Commun. doi:10.1038/ncomms11917
59. Wu S, Liu J, Li Z (2016b) Organic synthesis via oxidative cascade biocatalysis. Synlett DOI. doi:10.1055/s-0036-1588627
60. Xu Y, Jia X, Panke S, Li Z (2009) Asymmetric dihydroxylation of aryl olefins by sequential enantioselective epoxidation and regioselective hydrolysis with tandem biocatalysts. Chem Commun 12:1481–1483
61. Xu Y, Li A, Jia X, Li Z (2011) Asymmetric trans-dihydroxylation of cyclic olefins by enzymatic or chemo-enzymatic sequential epoxidation and hydrolysis in one-pot. Green Chem 13(9):2452–2458
62. Xue Y-P, Liu Z-Q, Xu M, Wang Y-J, Zheng Y-G, Shen Y-C (2010) Enhanced biotransformation of (R, S)-mandelonitrile to (R)-(−)-mandelic acid with in situ production removal by addition of resin. Biochem Eng J 53(1):143–149
63. Yang Y, Liu J, Li Z (2014) Engineering of P450pyr hydroxylase for the highly regio-and enantioselective subterminal hydroxylation of alkanes. Angew Chem Int Ed 53(12):3120–3124
64. Zhang W, Tang W, Wang ICD, Li Z (2011) Concurrent oxidations with tandem biocatalysts in one pot: green, selective and clean oxidations of methylene groups to ketones. Chem Commun 47(11):3284–3286
65. Zhang J, Xu T, Li Z (2013) Enantioselective biooxidation of racemic trans-cyclic vicinal diols: one-pot synthesis of both enantiopure (S, S)-cyclic vicinal diols and (R)-α-hydroxy ketones. Adv Synth Catal 355(16):3147–3153
66. Zhao L-Q, Sun Z-H, Zheng P, He J-Y (2006) Biotransformation of isoeugenol to vanillin by Bacillus fusiformis CGMCC1347 with the addition of resin HD-8. Process Biochem 41(7):1673–1676
67. Zhou Y, Wu S, Li Z (2016) Cascade biocatalysis for sustainable asymmetric synthesis: from biobased L-phenylalanine to high-value chiral chemicals. Angew Chem Int Ed 55(38):11647–11650