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Issue 15, 2012
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Second generation specific-enzyme-activated rotaxane propeptides

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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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Supplementary files

Article information


Submitted
29 Nov 2011
Accepted
14 Dec 2011
First published
16 Dec 2011

Chem. Commun., 2012,48, 2083-2085
Article type
Communication

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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