Construction and use of recombinant Escherichia coli strains for the synthesis of toluene cis-glycol

Wahbi, L. P.; Gokhale, D. V.; Minter, Stephen J.; Stephens, Gill

doi:10.1016/0141-0229(95)00249-9

Cited by 19 publications

(7 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is also important to note that there was no emulsion formation in any of the cultures grown with the ionic liquids, whereas there are serious problems with emulsification when tetradecane is used, due to release of surface active materials by the cells. [27][28][29][30] The only problem was that the conversion of toluene to toluene cis-glycol was incomplete (27% yield). However, the oxygen supply was restricted to the air available in the culture headspace because the culture vessels had to be sealed to prevent loss of substrate.…”

Section: Resultsmentioning

confidence: 99%

“…Further work is now needed to optimise the regimes for growth and toluene feeding to obtain reproducible biotransformation in the presence of ionic liquids in bioreactors, although the current cost of the ionic liquid takes this beyond the scope of academic research. Measurement of growth rates: Growth rates of E. coli K12 strain MG1655 33 were measured in MSX medium 27 in microcultures (200 ll including solvent) using a Bioscreen C incubator/plate reader (Thermo Labsystems, Franklin, MA). Biotransformation of toluene was tested using E. coli MG1655 transformed 34 with pDTG601A 35 (provided by Rebecca Parales, University of California, Davis).…”

Section: Resultsmentioning

confidence: 99%

“…Biotransformations: Cultures for small scale biotransformations (50 ml) 27 were grown at 37 • C and 200 rpm with toluene in the presence or absence of solvents at a phase ratio of 0.23. Isopropyl-b-D-thiogalactoside (IPTG; 1 mM) was added after 5 h. All solvents were self sterile, since there was no microbial growth when 1 ml solvent was incubated in sterile medium for 30 h at 37 • C. The phase ratio was kept constant by taking samples from both the aqueous and solvent phases in the required volume ratio.…”

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Using a biphasic ionic liquid/water reaction system to improve oxygenase-catalysed biotransformation with whole cells

et al. 2008

View full text Add to dashboard Cite

Whole cells are usually used for oxygenase-catalysed biotransformations to ensure efficient cofactor recycling and to avoid problems with purification and stability of these complex, multi-subunit enzymes. Productivity in oxygenase-catalysed biotransformations is frequently restricted by toxicity of the substrates to the cells, but attempting to solve this problem using two-liquid phase reaction systems with conventional solvents provides only modest improvements in productivity. Therefore, we developed new, two phase systems using water-immiscible ionic liquids. Even though [NMeOct 3 ][NTf 2 ] and [P 6,6,6,14 ][NTf 2 ], inhibited growth of Escherichia coli by 39% and 23% respectively, both ionic liquids could be used to improve toluene dioxygenase-catalysed conversion of toluene to toluene cis-glycol using recombinant E. coli cells. The two-liquid phase reaction system improved resistance to toluene toxicity by 8-fold, and product concentrations increased by 2.5-fold in shake flask cultures. Product concentrations and specific product yields were improved by 200% and 238% respectively in bioreactors with an unrestricted oxygen supply.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Using a biphasic ionic liquid/water reaction system to improve oxygenase-catalysed biotransformation with whole cells

et al. 2008

View full text Add to dashboard Cite

show abstract

“…Attempts to use recombinant E. coli strains to produce ®ne chemicals by redox-reactions have thus far concentrated on the production of dihydrodiols (Reddy et al, 1999;Tsai, et al, 1996;Wahbi et al, 1996;Wubbolts and Timmis, 1990;Zeyer et al, 1985), and alkanoic acids (Favre-Bulle et al, 1991;1993;Rothen et al, 1998;Wubbolts et al, 1996), or on pathway engineering requiring the incorporation of multiple reaction steps in a host cell (Draths and Frost, 1994;Draths et al, 1992a;1992b;French et al, 1995;Park et al, 1998). The latter approach has led to a process on the 30 m 3 scale for the production of indigo employingÐamong other enzymesÐrecombinant naphthalene dioxygenase, which is probably the ®rst commercial process development involving a recombinant oxygenase.…”

Section: Implications For Recombinant Biocatalysismentioning

confidence: 99%

Pilot‐scale production of (S)‐styrene oxide from styrene by recombinant Escherichia coli synthesizing styrene monooxygenase

Panke

Held

Wubbolts

et al. 2002

Biotech & Bioengineering

169

128

View full text Add to dashboard Cite

Recombinant Escherichia coli JM101(pSPZ10) cells produce the styrene monooxygenase of Pseudomonas sp. strain VLB120, which catalyzes the oxidation of styrene to (S)-styrene oxide at an enantiomeric excess larger than 99%. This biocatalyst was used to produce 388 g of styrene oxide in a two-liquid phase 30-L fed-batch bioconversion. The average overall volumetric activity was 170 U per liter over a period of more than 10 h, equivalent to mass transfer rates of 10.2 mmoles per liter per hour at a phase ratio of 0.5. At this transfer rate, the biotransformation system appeared to be substrate mass-transfer limited. The reactor had an estimated power input in the order of 5 W. L(-1), which is close to values typically obtained with commercially operating units. The product could be easily purified by fractional distillation to a purity in excess of 97%. The process illustrates the feasibility of recombinant whole cell biotransformations in two-liquid phase systems with toxic substrates and products.

show abstract

“…Benzene cis-diol, namely, cis-DHCD, is a chiral chemical which is important for the pharmaceutical and chemical industries (Hack et al 1994;Wahbi et al 1996Wahbi et al , 1997. It is one of the intermediates during biological aromatic oxidation in some microorganisms.…”

Section: Biocatalytic Production Of Cis-dhcdmentioning

confidence: 99%

Microbial cis-3,5-Cyclohexadiene-1,2-diol, Its Polymer Poly(p-phenylene), and Applications

Chen

2009

Microbiology Monographs

View full text Add to dashboard Cite

This chapter describes the production of cis-3,5-cyclohexadiene-1,2-diol (DHCD) from aromatic compounds, their polymerization into poly(p-phenyelene) (or PPP), and the properties and applications of the polymer. Large-scale synthesis of DHCD has been demonstrated, and DHCD is widely used in the pharmaceutical industry, as well as in chemical industries for polymer productions. Recent study including different types of dioxygenases, strain development by recombination, and genetical modification were done to develop the process technology for commercialization of this new polymer and chemical intermediates.

show abstract

Construction and use of recombinant Escherichia coli strains for the synthesis of toluene cis-glycol

Cited by 19 publications

References 22 publications

Using a biphasic ionic liquid/water reaction system to improve oxygenase-catalysed biotransformation with whole cells

Using a biphasic ionic liquid/water reaction system to improve oxygenase-catalysed biotransformation with whole cells

Pilot‐scale production of (S)‐styrene oxide from styrene by recombinant Escherichia coli synthesizing styrene monooxygenase

Microbial cis-3,5-Cyclohexadiene-1,2-diol, Its Polymer Poly(p-phenylene), and Applications

Contact Info

Product

Resources

About