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Synthesis of pyrrolidine-based hamamelitannin analogues as quorum sensing inhibitors in Staphylococcus aureus

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Abstract
Interfering with bacterial cell-to-cell communication is a promising strategy to combat antimicrobial resistance. The natural product hamamelitannin and several of its analogues have been identified as quorum sensing inhibitors. In this paper the synthesis of pyrrolidine-based analogues of a more lead-like hamamelitannin analogue is reported. A convergent synthetic route based on a key ring-closing metathesis reaction was developed and delivered the pyrrolidine analogue in 17 steps in high yield. Chemoselective derivatization of the pyrrolidine nitrogen atom resulted in 6 more compounds. The synthesized compounds were evaluated in a biofilm model, but were all inactive.
Keywords
hamamelitannin, iminosugar, pyrrolidine, quorum sensing, Staphylococcus aureus, MRSA INFECTIONS, POTENTIATORS, ANTIBIOTICS, VANCOMYCIN, DISCOVERY

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MLA
Bouton, Jakob et al. “Synthesis of Pyrrolidine-based Hamamelitannin Analogues as Quorum Sensing Inhibitors in Staphylococcus Aureus.” BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 14 (2018): 2822–2828. Print.
APA
Bouton, J., Van Hecke, K., Rasooly, R., & Van Calenbergh, S. (2018). Synthesis of pyrrolidine-based hamamelitannin analogues as quorum sensing inhibitors in Staphylococcus aureus. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 14, 2822–2828.
Chicago author-date
Bouton, Jakob, Kristof Van Hecke, Reuven Rasooly, and Serge Van Calenbergh. 2018. “Synthesis of Pyrrolidine-based Hamamelitannin Analogues as Quorum Sensing Inhibitors in Staphylococcus Aureus.” Beilstein Journal of Organic Chemistry 14: 2822–2828.
Chicago author-date (all authors)
Bouton, Jakob, Kristof Van Hecke, Reuven Rasooly, and Serge Van Calenbergh. 2018. “Synthesis of Pyrrolidine-based Hamamelitannin Analogues as Quorum Sensing Inhibitors in Staphylococcus Aureus.” Beilstein Journal of Organic Chemistry 14: 2822–2828.
Vancouver
1.
Bouton J, Van Hecke K, Rasooly R, Van Calenbergh S. Synthesis of pyrrolidine-based hamamelitannin analogues as quorum sensing inhibitors in Staphylococcus aureus. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. 2018;14:2822–8.
IEEE
[1]
J. Bouton, K. Van Hecke, R. Rasooly, and S. Van Calenbergh, “Synthesis of pyrrolidine-based hamamelitannin analogues as quorum sensing inhibitors in Staphylococcus aureus,” BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol. 14, pp. 2822–2828, 2018.
@article{8581805,
  abstract     = {Interfering with bacterial cell-to-cell communication is a promising strategy to combat antimicrobial resistance. The natural product hamamelitannin and several of its analogues have been identified as quorum sensing inhibitors. In this paper the synthesis of pyrrolidine-based analogues of a more lead-like hamamelitannin analogue is reported. A convergent synthetic route based on a key ring-closing metathesis reaction was developed and delivered the pyrrolidine analogue in 17 steps in high yield. Chemoselective derivatization of the pyrrolidine nitrogen atom resulted in 6 more compounds. The synthesized compounds were evaluated in a biofilm model, but were all inactive.},
  author       = {Bouton, Jakob and Van Hecke, Kristof and Rasooly, Reuven and Van Calenbergh, Serge},
  issn         = {1860-5397},
  journal      = {BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY},
  keywords     = {hamamelitannin,iminosugar,pyrrolidine,quorum sensing,Staphylococcus aureus,MRSA INFECTIONS,POTENTIATORS,ANTIBIOTICS,VANCOMYCIN,DISCOVERY},
  language     = {eng},
  pages        = {2822--2828},
  title        = {Synthesis of pyrrolidine-based hamamelitannin analogues as quorum sensing inhibitors in Staphylococcus aureus},
  url          = {http://dx.doi.org/10.3762/bjoc.14.260},
  volume       = {14},
  year         = {2018},
}

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