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Geminal dihalogen isosteric replacement in hydrated AI-2 affords potent quorum sensing modulators.
Guo, Min; Zheng, Yue; Terell, Jessica L; Ad, Michal; Opoku-Temeng, Clement; Bentley, William E; Sintim, Herman O.
Affiliation
  • Guo M; Department of Chemistry and Biochemistry, University of Maryland College Park, 20742, USA. hsintim@umd.edu.
Chem Commun (Camb) ; 51(13): 2617-20, 2015 Feb 14.
Article in En | MEDLINE | ID: mdl-25573337
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.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Quorum Sensing / Homoserine / Lactones Type of study: Prognostic_studies Language: En Journal: Chem Commun (Camb) Journal subject: QUIMICA Year: 2015 Document type: Article Affiliation country: Estados Unidos
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Quorum Sensing / Homoserine / Lactones Type of study: Prognostic_studies Language: En Journal: Chem Commun (Camb) Journal subject: QUIMICA Year: 2015 Document type: Article Affiliation country: Estados Unidos