Protein-mediated dethreading of a biotin-functionalised pseudorotaxane

Caldwell, S.T. et al. (2014) Protein-mediated dethreading of a biotin-functionalised pseudorotaxane. Organic and Biomolecular Chemistry, 12(3), pp. 511-516. (doi: 10.1039/C3OB41612G) (PMID:24280954)

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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-(4prime or minute-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.

Item Type:Articles
Glasgow Author(s) Enlighten ID:Caldwell, Dr Stuart and Nutley, Mrs Margaret and Cooke, Professor Graeme and Riehle, Dr Mathis and Rabani, Dr Gouher and Smith, Dr Brian and Cooper, Professor Alan and Fitzpatrick, Dr Brian
Authors: Caldwell, S.T., Maclean, C., Riehle, M., Cooper, A., Nutley, M., Rabani, G., Fitzpatrick, B., Rotello, V.M., Smith, B.O., Khaled, B., Woisel, P., and Cooke, G.
Subjects:Q Science > QD Chemistry
College/School:College of Medical Veterinary and Life Sciences > School of Molecular Biosciences
College of Science and Engineering > School of Chemistry
Journal Name:Organic and Biomolecular Chemistry
Publisher:Royal Society of Chemistry
ISSN (Online):1477-0539
Published Online:27 November 2013
Copyright Holders:Copyright © 2014 The Royal Society of Chemistry
First Published:First published in Scientific World Journal 2013:838042
Publisher Policy:Reproduced under a Creative Commons License

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