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Solution structural features of N-acyl homoserine lactones

Tumminakatti, Shama and Khatri, Bhavesh and Krishnamurti, Vinayak and Athavale, Vishikh and Prabhakaran, Erode N (2015) Solution structural features of N-acyl homoserine lactones. In: TETRAHEDRON LETTERS, 56 (42). pp. 5771-5775.

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Official URL: http://dx.doi.org/10.1016/j.tetlet.2015.08.078

Abstract

Here we demonstrate that in interbacterial quorum signal moderators, N-acylhomoserine lactones (AHLs), the stabilization of bioactive pharmacophore lactone against lysis is through the e(-) withdrawing N-acyl motif which reduces lactone carbonyl polarization. This lysis is assisted by weak (<0.05 kcal mol(-1)) contacts between N-acyl O and lactone C'. The interactions that preclude this weak contact, in the free and receptor-bound AHLs, improve lactone halflife and hence are key to the design of the antibacterial AHL analogues. (C) 2015 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the PERGAMON-ELSEVIER SCIENCE LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Keywords: AHL; Bimodular; Lactone; n -> pi*; Solvolysis
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 31 Oct 2015 05:59
Last Modified: 31 Oct 2015 05:59
URI: http://eprints.iisc.ac.in/id/eprint/52631

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