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Issue 3, 2014
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Protein-mediated dethreading of a biotin-functionalised pseudorotaxane

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Abstract

In this article, we describe the synthesis of new biotin-functionalised naphthalene derivatives 3 and 4 and their complexation behaviour with avidin and neutravidin using a range of analytical techniques. We have shown using 2-(4′-hydroxyazobenzene)benzoic acid displacement and ITC experiments, that compounds 3 and 4 have the propensity to form reasonably high-affinity bioconjugates with avidin and neutravidin. We have also demonstrated using 1H NMR, UV-vis and fluorescence spectroscopy that the naphthalene moiety of 3 and 4 facilitates the formation of pseudorotaxane-like structures with 1 in water. We have then investigated the ability of avidin and neutravidin to modulate the complexation between 1 and 3 or 4. UV-vis and fluorescence spectroscopy has shown that in both cases the addition of the protein disrupts complexation between the naphthalene moieties of 3 and 4 with 1.

Graphical abstract: Protein-mediated dethreading of a biotin-functionalised pseudorotaxane

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Publication details

The article was received on 07 Aug 2013, accepted on 14 Nov 2013 and first published on 27 Nov 2013


Article type: Paper
DOI: 10.1039/C3OB41612G
Citation: Org. Biomol. Chem., 2014,12, 511-516
  • Open access: Creative Commons BY license
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    Protein-mediated dethreading of a biotin-functionalised pseudorotaxane

    S. T. Caldwell, C. Maclean, M. Riehle, A. Cooper, M. Nutley, G. Rabani, B. Fitzpatrick, V. M. Rotello, B. O. Smith, B. Khaled, P. Woisel and G. Cooke, Org. Biomol. Chem., 2014, 12, 511
    DOI: 10.1039/C3OB41612G

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