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Enzymatic Method for N-Acyl Homoserine Lactones Synthesis Using Immobilized Candida antarctica Lipase

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Abstract

An enzymatic method to produce N-acyl homoserine lactones (AHLs) is described. This report represents the first example of the synthesis of bioactive AHLs using immobilized Candida antarctica lipase as the catalyst. The reaction yields, evaluated by GC-EIMS, ranged from 6 to 99%.

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References

  1. Parsek M, Val D, Hanzelka B et al (1999) Proc Natl Acad Sci USA 96:4360

    Article  CAS  Google Scholar 

  2. Fuqua C, Greenberg EP (2002) Nat Rev Mol Cell Biol 3:685

    Article  CAS  Google Scholar 

  3. Engebrecht J, Nealson K, Silverman M (1983) Cell 32:773

    Article  CAS  Google Scholar 

  4. Dickschat JS (2010) Nat Prod Rep 27:343

    Article  CAS  Google Scholar 

  5. Thomson NR, Crow MA, McGowan SJ et al (2000) Mol Microbiol 36:539

    Article  CAS  Google Scholar 

  6. Whitehead NA, Barnard AML, Slater H et al (2001) FEMS Microbiol Rev 25:365

    Article  CAS  Google Scholar 

  7. Defoirdt T, Brackman G, Coenye T (2013) Trends Microbiol 21:619

    Article  CAS  Google Scholar 

  8. Kievit T, De Gillis R, Marx S et al (2001) Appl Environ Microbiol 67:1865

    Article  Google Scholar 

  9. Sepahi E, Tarighi S, Ahmadi FS, Bagheri A (2015) J Microbiol 53:176

    Article  CAS  Google Scholar 

  10. Càmara M, Daykin M, Chhabra SR (1998) In: Williams P (ed) Methods microbiology: bacterial pathogenesis, vol 27. Academic Press, London

    Google Scholar 

  11. Ruysbergh E, Stevens CV, De Kimpe N, Mangelinckx S (2016) RSC Adv 6:73717

    Article  CAS  Google Scholar 

  12. Wang R, Hou M, Zhang Y et al (2015) Catal Lett 145:995

    Article  CAS  Google Scholar 

  13. Gotor-Fernández V, Busto E, Gotor V (2006) Adv Synth Catal 348:797

    Article  Google Scholar 

  14. Molina-Torres J, Santos-Escobar F, González-Arnao MT et al (2008) Lat Am J Pharm 27:852

    CAS  Google Scholar 

  15. Whitten KM, Makriyannis A, Vadivel SK (2012) Tetrahedron Lett 53:5753

    Article  CAS  Google Scholar 

  16. Kobata K, Kawamura M, Toyoshima M et al (1998) Biotechnol Lett 20:451

    Article  CAS  Google Scholar 

  17. McClean K, Winson M, Fish L (1997) Microbiology 143:3703

    Article  CAS  Google Scholar 

  18. Weihua C, Dhiraj AV, Vatsala M, et al, In: Rumbaugh KP (ed) Quorum sensing methods and protocols (2011) Humana Press, Hatfield

    Google Scholar 

  19. Cataldi TRI, Bianco G, Frommberger M, Schmitt-Kopplin P (2004) Rapid Commun Mass Spectrom 18:1341

    Article  CAS  Google Scholar 

  20. Kuo A, Callahan SM, Dunlap PV (1996) J Bacteriol 178:971

    Article  CAS  Google Scholar 

  21. Ikeda T, Kajiyama K, Kita T et al (2001) Chem Lett 4:314

    Article  Google Scholar 

Download references

Acknowledgements

Authors thank CONACyT for funding this research and for the scholarship granted to Juan Vázquez-Martínez. We woul like to thank Carolyn Smith, Peace Corps volunteer for proof reading the manuscript.

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Authors and Affiliations

  1. Departamento de Biotecnología y Bioquímica, Centro de Investigación y de Estudios Avanzados del IPN (CINVESTAV), Unidad Irapuato, Libramiento Norte Km 9.6, 36824, Irapuato., Guanajuato, Mexico

    Juan Vázquez-Martínez, Edgar Nieto-Álvarez, Enrique Ramírez-Chávez & Jorge Molina-Torres

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  1. Juan Vázquez-Martínez
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  2. Edgar Nieto-Álvarez
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  3. Enrique Ramírez-Chávez
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  4. Jorge Molina-Torres
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Correspondence to Jorge Molina-Torres.

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The authors declare that they have no conflict of interest.

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Vázquez-Martínez, J., Nieto-Álvarez, E., Ramírez-Chávez, E. et al. Enzymatic Method for N-Acyl Homoserine Lactones Synthesis Using Immobilized Candida antarctica Lipase. Catal Lett 148, 62–67 (2018). https://doi.org/10.1007/s10562-017-2261-8

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  • DOI: https://doi.org/10.1007/s10562-017-2261-8

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