Second generation specific-enzyme-activated rotaxane propeptides.
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.
School of Chemistry, University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh, EH9 3JJ, UK.
Antony
A
Fernandes
Aurélien
A
Viterisi
Vincent
V
Aucagne
David A
DA
Leigh
Sébastien
S
Papot
D004926:Escherichia coli / Q000201:enzymology; D019855:Ethylene Glycol / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D010455:Peptides / Q000737:chemistry* / Q000378:metabolism; D043862:Rotaxanes / Q000737:chemistry* / Q000378:metabolism; D012995:Solubility; D001616:beta-Galactosidase / Q000378:metabolism
D010455:Peptides; D043862:Rotaxanes; D001616:beta-Galactosidase; D019855:Ethylene Glycol