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15α-Hydroxylation of a steroid (13-ethyl-gon-4-en-3,17-dione) by Penicillium raistrickii in an ionic liquid/aqueous biphasic system

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Abstract

Biphasic processes are used in whole-cell biotransformation to overcome the low water solubility of substrates and products as well as their inhibitory effects on the biocatalyst. Commercially available [NTf2]- and [PF6]-based ionic liquids (ILs) were used in a biphasic system for the 15α-hydroxylation of 13-ethyl-gon-4-en-3,17-dione by Penicillium raistrickii. With the substrate at 5 g l−1 and a volume ratio of IL to buffer, buffer pH and cell density at, 1:9, 6.5, 16.8 gDW l−1, respectively, the 15α-hydroxylation of 13-ethyl-gon-4-en-3,17-dione was achieved with a yield of 70 % after 72 h using [BMIm][NTf2] in a 50 ml biphasic system. This is compared to a 30 % yield in a monophasic aqueous system. This suggests the potential industrial application of ILs-based biphasic systems for steroid biotransformation.

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References

  • Angelova B, Fernandes P, Cruz A, Pinheiro HM, Mutafov S, Cabral JMS (2005) Hydroxylation of androstenedione by resting Rhodococcus sp. cells in organic media. Enzyme Microb Technol 37:718–722

    Article  CAS  Google Scholar 

  • Brautigam S, Bringer-Meyer S, Weuster-Botz D (2007) Asymmetric whole cell biotransformations in biphasic ionic liquid/water-systems by use of recombinant Escherichia coli with intracellular cofactor regeneration. Tetrahedron: Asymmetry 18:1883–1887

    Article  Google Scholar 

  • Couling DJ, Bernot RJ, Docherty KM, Dixon JK, Maginn EJ (2006) Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure-property relationship modeling. Green Chem 8:82–90

    Article  CAS  Google Scholar 

  • Gangu SA, Weatherley LR, Scurto AM (2009) Whole-cell biocatalysis with ionic liquids. Curr Org Chem 13:1242–1258

    Article  CAS  Google Scholar 

  • Heipieper HJ, Neumann G, Cornelissen S, Meinhardt F (2007) Solvent-tolerant bacteria for biotransformations in two-phase fermentation systems. Appl Microbiol Biotechnol 74:961–973

    Article  PubMed  CAS  Google Scholar 

  • Lou WY, Chen L, Zhang BB, Smith TJ, Zong MH (2009) Using a water-immiscible ionic liquid to improve asymmetric reduction of 4-(trimethylsilyl)-3-butyn-2-one catalyzed by immobilized Candida parapsilosis CCTCC M203011 cells. BMC Biotechnol 9:90–101

    Article  PubMed  Google Scholar 

  • Luis P, Garea A, Irabien A (2010) Quantitative structure–activity relationships (QSARs) to estimate ionic liquids ecotoxicity EC50 (Vibrio fischeri). J Mol Liq 152:28–33

    Article  CAS  Google Scholar 

  • Oppermann S, Stein F, Kragl U (2011) Ionic liquids for two-phase systems and their application for purification, extraction and biocatalysis. Appl Microbiol Biotechnol 89:493–499

    Article  PubMed  CAS  Google Scholar 

  • Pfrunder H, Jones R, Weuster-Botz D (2006) Water immiscible ionic liquids as solvents for whole cell biocatalysis. J Biotechnol 24:182–190

    Article  Google Scholar 

  • Roosen C, Mueller P, Greiner L (2008) Ionic liquids in biotechnology: applications and perspectives for biotransformations. Appl Microbiol Biotechnol 81:607–614

    Article  PubMed  CAS  Google Scholar 

  • Schlosser D, Irrgang S, Schmauder HP (1993) Steroid hydroxylation with free and immobilized cells of Penicillium raistrickii in the presence of β-cyclodextrin. Appl Microbiol Biotechnol 39:16–20

    PubMed  CAS  Google Scholar 

  • Wang W, Zong MH, Lou WY (2009) Use of an ionic liquid to improve asymmetric reduction of 4′-methoxyacetophenone catalyzed by immobilized Rhodotorula sp. AS2.2241 cells. J Mol Catal B: Enzym 56:70–76

    Article  CAS  Google Scholar 

  • Weuster-Botz D (2007) Process intensification of whole-cell biocatalysis with ionic liquids. Chem Rec 7:334–340

    Article  PubMed  CAS  Google Scholar 

  • Wu DX, Guan YX, Wang HQ, Yao SJ (2011) 11α-Hydroxylation of 16α,17-epoxyprogesterone by Rhizopus nigricans in a biphasic ionic liquid aqueous system. Bioresour Technol 102:9368–9373

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgments

This work was financially supported by Grants from the National High Technology Research and Development Program of China (863 Program) (No. 2011AA02A211), Applied Basic Research Programs of Science and Technology Commission Foundation of Tianjin (No.12JCQNJC06400) and the Foundation (No. 201004) of Tianjin Key Laboratory of Marine Resources and Chemistry (Tianjin University of Science & Technology).

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Correspondence to Fuping Lu.

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Mao, S., Hu, X., Hua, B. et al. 15α-Hydroxylation of a steroid (13-ethyl-gon-4-en-3,17-dione) by Penicillium raistrickii in an ionic liquid/aqueous biphasic system. Biotechnol Lett 34, 2113–2117 (2012). https://doi.org/10.1007/s10529-012-1016-2

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  • DOI: https://doi.org/10.1007/s10529-012-1016-2

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