Conformational studies of Gram-negative bacterial quorum sensing 3-oxo N -acyl homoserine lactone molecules

Darren Crowe; Alan Nicholson; Adrienne FlemingEd CareyGoar Sánchez-SanzFintan Kelleher

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Conformational studies of Gram-negative bacterial quorum sensing 3-oxo N -acyl homoserine lactone molecules

机译：Conformational studies of Gram-negative bacterial quorum sensing 3-oxo N -acyl homoserine lactone molecules

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Graphical abstract Display Omitted Highlights ? H-bond stabilised lowest energy conformation of keto tautomer of OHLs. ? Measurement of Kt for OHLs in CDCl 3 by 1 H NMR spectroscopy. ? DFT calculations of OHL keto/enol tautomers in gas phase and solvent models. ? DFT calculations of OHL analogue keto/enol tautomers in gas phase & solvent models. ? Demonstration of flexibility of OHL conformations in gas phase and solvent models. Abstract In their 1 H NMR spectra in CDCl 3 3-oxo- N -acyl homoserine lactones (OHLs) show significant downfield chemical shifts of the amide N H proton when compared to the parent N -acyl homoserine lactones (AHLs). NMR spectroscopic and DFT calculation studies have shown that this is most likely due to the presence of a stabilising intramolecular H-bond from the N H to the 3-oxo group. The 1 H NMR spectra also show evidence for the enol tautomers and that the amount of enol present for a range of OHLs is 4.1–4.5% in CDCl 3 and 6.5–7.2% in CD 3 CN. In contrast, DFT calculations show that the lowest energy enol tautomer and the keto tautomer are of equal energy in the gas phase, but that the keto tautomer is more stable in chloroform, acetonitrile and water solution. The calculations also show that there is no evidence for any n → π ? or C5H-bonding interactions being present in either the lowest energy keto or enol tautomer of the OHLs in solution or the gas phase, which is in contrast to the reported solid-state structure. ]]>

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《Bioorganic and medicinal chemistry》 |2017年第16期|4285-4296|共12页
作者
Darren Crowe; Alan Nicholson; Adrienne FlemingEd CareyGoar Sánchez-SanzFintan Kelleher;
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作者单位

Molecular Design and Synthesis Group, Centre of Applied Science for Health, Institute of Technology;

Irish Centre of High-End Computing;

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原文格式 PDF
正文语种英语
中图分类药学;
关键词
Homoserine lactones; β-Keto amide; DFT calculations; Keto-enol tautomers; Quorum sensing;

Conformational studies of Gram-negative bacterial quorum sensing 3-oxo N -acyl homoserine lactone molecules

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