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%.
Graphical Abstract
Similar content being viewed by others
References
Parsek M, Val D, Hanzelka B et al (1999) Proc Natl Acad Sci USA 96:4360
Fuqua C, Greenberg EP (2002) Nat Rev Mol Cell Biol 3:685
Engebrecht J, Nealson K, Silverman M (1983) Cell 32:773
Dickschat JS (2010) Nat Prod Rep 27:343
Thomson NR, Crow MA, McGowan SJ et al (2000) Mol Microbiol 36:539
Whitehead NA, Barnard AML, Slater H et al (2001) FEMS Microbiol Rev 25:365
Defoirdt T, Brackman G, Coenye T (2013) Trends Microbiol 21:619
Kievit T, De Gillis R, Marx S et al (2001) Appl Environ Microbiol 67:1865
Sepahi E, Tarighi S, Ahmadi FS, Bagheri A (2015) J Microbiol 53:176
Càmara M, Daykin M, Chhabra SR (1998) In: Williams P (ed) Methods microbiology: bacterial pathogenesis, vol 27. Academic Press, London
Ruysbergh E, Stevens CV, De Kimpe N, Mangelinckx S (2016) RSC Adv 6:73717
Wang R, Hou M, Zhang Y et al (2015) Catal Lett 145:995
Gotor-Fernández V, Busto E, Gotor V (2006) Adv Synth Catal 348:797
Molina-Torres J, Santos-Escobar F, González-Arnao MT et al (2008) Lat Am J Pharm 27:852
Whitten KM, Makriyannis A, Vadivel SK (2012) Tetrahedron Lett 53:5753
Kobata K, Kawamura M, Toyoshima M et al (1998) Biotechnol Lett 20:451
McClean K, Winson M, Fish L (1997) Microbiology 143:3703
Weihua C, Dhiraj AV, Vatsala M, et al, In: Rumbaugh KP (ed) Quorum sensing methods and protocols (2011) Humana Press, Hatfield
Cataldi TRI, Bianco G, Frommberger M, Schmitt-Kopplin P (2004) Rapid Commun Mass Spectrom 18:1341
Kuo A, Callahan SM, Dunlap PV (1996) J Bacteriol 178:971
Ikeda T, Kajiyama K, Kita T et al (2001) Chem Lett 4:314
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.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-017-2261-8