Second generation specific-enzyme-activated rotaxane propeptides.

Antony Fernandes 1 Aurélien Viterisi 2 Vincent Aucagne 3 David A Leigh 2 Sébastien Papot 4
1 Synthèse Organique
The School of Chemistry, IC2MP - Institut de Chimie des Milieux et Matériaux de Poitiers
4 Synthèse Organique
IC2MP - Institut de Chimie des Milieux et Matériaux de Poitiers
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.
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Submitted on : Tuesday, March 13, 2012 - 5:25:30 PM
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Antony Fernandes, Aurélien Viterisi, Vincent Aucagne, David A Leigh, Sébastien Papot. Second generation specific-enzyme-activated rotaxane propeptides.. Chemical Communications, Royal Society of Chemistry, 2012, 48 (15), pp.2083-5. ⟨10.1039/c2cc17458h⟩. ⟨hal-00678757⟩



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