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Molecules 2013, 18(9), 11553-11575; doi:10.3390/molecules180911553

A pH-Sensitive Peptide-Containing Lasso Molecular Switch

,  and *
Supramolecular Machines and ARchitectures Team, Institut des Biomolécules Max Mousseron, (IBMM) UMR 5247 CNRS-UM1-UM2, Université Montpellier 2, Place Eugène Bataillon, Case Courrier 1706, F-34095 Montpellier Cedex 5, France
* Author to whom correspondence should be addressed.
Received: 24 July 2013 / Revised: 9 September 2013 / Accepted: 11 September 2013 / Published: 17 September 2013
(This article belongs to the Special Issue Rotaxanes)
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The synthesis of a peptide-containing lasso molecular switch by a self-entanglement strategy is described. The interlocked [1] rotaxane molecular machine consists of a benzometaphenylene[25]crown-8 (BMP25C8) macrocycle surrounding a molecular axle. This molecular axle contains a tripeptidic sequence and two molecular stations: a N-benzyltriazolium and a pH-sensitive anilinium station. The tripeptide is located between the macrocycle and the triazolium station, so that its conformation can be tailored depending on the shuttling of the macrocycle from one station to the other. At acidic pH, the macrocycle resides around the anilinium moiety, whereas it shuttles around the triazolium station after deprotonation. This molecular machinery thus forces the lasso to adopt a tightened or a loosened conformation.
Keywords: [1]rotaxane; lasso; molecular switch; self-entanglement; peptide [1]rotaxane; lasso; molecular switch; self-entanglement; peptide
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Clavel, C.; Fournel-Marotte, K.; Coutrot, F. A pH-Sensitive Peptide-Containing Lasso Molecular Switch. Molecules 2013, 18, 11553-11575.

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