ArticleACS chemical biology2014
A key n→π* Interaction in N-acyl homoserine lactones.
Article in ACS chemical biology, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 64 citations in OpenAlex.
- The interplay between the pyramidalization of carbonyl carbons and the n → π* interactions in biomolecules.Protein science : a publication of the Protein Society · 2026Article
- 4D Printing of Renewable Materials Derived from Glycerol and Maleic Anhydride with Tunable Thermal, Mechanical, and Fluorescent Properties.ACS omega · 2026Article
- Unveiling the Potential of Haloalkenes as Electron Density Acceptors.Crystal growth & design · 2024Article
- Article
- Structural preferences of cysteine sulfinic acid: The sulfinate engages in multiple local interactions with the peptide backbone.Free radical biology & medicine · 2020Article
- Relative orientation of the carbonyl groups determines the nature of orbital interactions in carbonyl-carbonyl short contacts.Chemical science · 2019Article
- The n→π* Interaction.Accounts of chemical research · 2017Article
- Reciprocal carbonyl-carbonyl interactions in small molecules and proteins.Nature communications · 2017Article
- Attractive Interactions between Heteroallenes and the Cucurbituril Portal.Journal of the American Chemical Society · 2017Article
- Stereodivergent, Diels-Alder-initiated organocascades employing α,β-unsaturated acylammonium salts: scope, mechanism, and application.Chemical science · 2017Article
- n→π* Interactions Are Competitive with Hydrogen Bonds.Organic letters · 2016Article
- Crystal structure of N-(3-oxo-butano-yl)-l-homoserine lactone.Acta crystallographica. Section E, Crystallographic communications · 2016Article
- n→π* interactions engender chirality in carbonyl groups.Organic letters · 2014Article
- Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators.Beilstein journal of organic chemistry · 2014Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Many Gram-negative bacteria employ N-acyl homoserine lactones (AHLs) as signal molecules for quorum sensing. The binding of AHLs to their target LuxR-type receptor proteins can effect changes in growth, virulence, and other phenotypes. LuxR-type receptors therefore present attractive pharmaceutical targets for control of bacterial pathogenesis. Here, we present X-ray crystallographic and computational evidence that the conformation of free AHLs is biased away from the conformation observed when bound to their cognate receptor due to the influence of an n→π* interaction. In this n→π* interaction, the p-type lone pair (n) of the N-acyl oxygen overlaps with the π* orbital of the lactone carbonyl group. This overlap results in the release of approximately 0.64 kcal/mol of energy. We also show that this interaction can be attenuated by installing electron-withdrawing groups on the N-acyl chain. Modulating this previously unappreciated interaction could present a new avenue toward effective inhibitors of bacterial quorum sensing.
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