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

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TitleGeminal dihalogen isosteric replacement in hydrated AI-2 affords potent quorum sensing modulators.
Publication TypeJournal Article
Year of Publication2015
AuthorsGuo, M, Zheng, Y, Terell, JL, Ad, M, Opoku-Temeng, C, Bentley, WE, Sintim, HO
JournalChem Commun (Camb)
Volume51
Issue13
Pagination2617-20
Date Published2015 Feb 14
ISSN1364-548X
KeywordsBinding Sites, Escherichia coli Proteins, Homoserine, Hydrogen Bonding, Lactones, Ligands, Models, Molecular, Molecular Conformation, Quorum Sensing, Repressor Proteins, Water
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.

DOI10.1039/c4cc09361e
Alternate JournalChem. Commun. (Camb.)
PubMed ID25573337
Grant List / / Howard Hughes Medical Institute / United States