Next Article in Journal
Synthesis of a Novel Carbocyclic Analog of Bredinin
Next Article in Special Issue
A Piston-Rotaxane with Two Potential Stripes: Force Transitions and Yield Stresses
Previous Article in Journal
Analysis of Biotinylated Generation 4 Poly(amidoamine) (PAMAM) Dendrimer Distribution in the Rat Brain and Toxicity in a Cellular Model of the Blood-Brain Barrier
Molecules 2013, 18(9), 11553-11575; doi:10.3390/molecules180911553
Article

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)
Download PDF [2753 KB, uploaded 18 June 2014]

Abstract

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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Export to BibTeX |
EndNote


MDPI and ACS Style

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

View more citation formats

Supplement

Related Articles

Article Metrics

Comments

Citing Articles

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert