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Issue 13, 2015
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Geminal dihalogen isosteric replacement in hydrated AI-2 affords potent quorum sensing modulators

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Abstract

Hydrated carbonyl groups in AI-2, a quorum sensing autoinducer, make key hydrogen bonding interactions in the binding site of LsrR (a transcriptional regulator). This can be recapitulated with geminal dibromides, via halogen bonding. Geminal dihalogens represent interesting isosteric replacements for hydrated carbonyls in ligands and are currently under-utilized in ligand design.

Graphical abstract: Geminal dihalogen isosteric replacement in hydrated AI-2 affords potent quorum sensing modulators

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Publication details

The article was received on 24 Nov 2014, accepted on 23 Dec 2014 and first published on 24 Dec 2014


Article type: Communication
DOI: 10.1039/C4CC09361E
Citation: Chem. Commun., 2015,51, 2617-2620
  • Open access: Creative Commons BY-NC license
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    Geminal dihalogen isosteric replacement in hydrated AI-2 affords potent quorum sensing modulators

    M. Guo, Y. Zheng, J. L. Terell, M. Ad, C. Opoku-Temeng, W. E. Bentley and H. O. Sintim, Chem. Commun., 2015, 51, 2617
    DOI: 10.1039/C4CC09361E

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