Issue 13, 2015
From the journal:

Chemical Communications

Geminal dihalogen isosteric replacement in hydrated AI-2 affords potent quorum sensing modulators†

Min Guo,a   Yue Zheng,a   Jessica L. Terell,b   Michal Ad,a   Clement Opoku-Temeng,a   William E. Bentleyb  and  Herman O. Sintim*a  

* Corresponding authors

a Department of Chemistry and Biochemistry, University of Maryland College Park, USA
E-mail: hsintim@umd.edu
Fax: +1 301 314 9121
Tel: +1 301 405 0633

b Fischell Department of Bioengineering, University of Maryland, College Park, USA

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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Article information

DOI
https://doi.org/10.1039/C4CC09361E
Article type
Communication
Submitted
24 Nov 2014
Accepted
23 Dec 2014
First published
24 Dec 2014
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2015,51, 2617-2620

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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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