Issue 15, 2012
From the journal:

Chemical Communications

Second generation specific-enzyme-activated rotaxane propeptides†

Antony Fernandes,‡ab   Aurélien Viterisi,‡a   Vincent Aucagne,*c   David A. Leigh*a  and  Sébastien Papot*b  

* Corresponding authors

a School of Chemistry, University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh, UK
E-mail: david.leigh@ed.ac.uk
Web: http://www.catenane.net
Fax: (+44) 131-650-6453

b Université de Poitiers, UMR-CNRS 6514, Laboratoire de Synthèse et Réactivité des Substances Naturelles, 4 rue Michel Brunet, BP 633, 86022 Poitiers, France
E-mail: sebastien.papot@univ-poitiers.fr

c Centre de Biophysique Moléculaire, UPR 4301 CNRS, Rue Charles Sadron, 45071 Orléans, Cedex 2, France
E-mail: aucagne@cnrs-orleans.fr

Abstract

A [2]rotaxane, in which the peptidic axle is protected from degradation by the macrocyclic sheath and terminated with a novel glycosidase-cleavable stopper, is rendered water-soluble by derivatisation with tetra(ethylene glycol) (TetEG) or glucosylated tetra(ethylene glycol) (Glc-TetEG) chains using the CuAAC ‘click’ reaction. The Glc-TetEG-derivatised rotaxane propeptide is >50 000 times more soluble in aqueous media than the parent rotaxane. Activation of the water-soluble rotaxane propeptide with a β-galactosidase efficiently releases the parent peptide.

Graphical abstract: Second generation specific-enzyme-activated rotaxane propeptides

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Article information

DOI
https://doi.org/10.1039/C2CC17458H
Article type
Communication
Submitted
29 Nov 2011
Accepted
14 Dec 2011
First published
16 Dec 2011

Chem. Commun., 2012,48, 2083-2085

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Second generation specific-enzyme-activated rotaxane propeptides

A. Fernandes, A. Viterisi, V. Aucagne, D. A. Leigh and S. Papot, Chem. Commun., 2012, 48, 2083 DOI: 10.1039/C2CC17458H

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