Journal
CHEMICAL COMMUNICATIONS
Volume 48, Issue 15, Pages 2083-2085Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2cc17458h
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Funding
- Science and Technology Department of the French Embassy in the United Kingdom
- Scottish Executive
- Royal Society of Edinburgh and the Engineering and Physical Sciences Research Council (EPSRC)
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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 beta-galactosidase efficiently releases the parent peptide.
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