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C4-alkoxy-hpd: A potent class of synthetic modulators surpassing nature in al-2 quorum sensing

Academic Article
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Overview

authors

  • Tsuchikama, K.
  • Zhu, Jie
  • Lowery, Colin
  • Kaufmann, Gunnar
  • Janda, Kim

publication date

  • August 2012

journal

  • Journal of the American Chemical Society  Journal

abstract

  • Bacteria have developed cell-to-cell communication mechanisms, termed quorum sensing (QS), that regulate bacterial gene expression in a cell population-dependent manner. Autoinducer-2 (AI-2), a class of QS signaling molecules derived from (4S)-4,5-dihydroxy-2,3-pentanedione (DPD), has been identified in both Gram-negative and Gram-positive bacteria. Despite considerable interest in the AI-2 QS system, the biomolecular communication used by distinct bacterial species still remains shrouded. Herein, we report the synthesis and evaluation of a new class of DPD analogues, C4-alkoxy-5-hydroxy-2,3-pentanediones, termed C4-alkoxy-HPDs. Remarkably, two of the analogues were more potent QS agonists than the natural ligand, DPD, in Vibrio harveyi. The findings presented extend insights into ligand-receptor recognition/signaling in the AI-2 mediated QS system.

subject areas

  • Anti-Bacterial Agents
  • Drug Discovery
  • Humans
  • Pentanes
  • Quorum Sensing
  • Vibrio
  • Vibrio Infections
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Identity

PubMed Central ID

  • PMC3438919

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja305532y

PubMed ID

  • 22866957
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Additional Document Info

start page

  • 13562

end page

  • 13564

volume

  • 134

issue

  • 33

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