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Coiled coil type neoglycoproteins presenting three lactose residues

Sweeney, Sinclair M.; Bullen, Gemma A.; Gillis, Richard B.; Adams, Gary G.; Rowe, Arthur J.; Harding, Stephen E.; Tucker, James H.R.; Peacock, Anna F.A.; Murphy, Paul V.

Authors

Sinclair M. Sweeney

Gemma A. Bullen

Richard B. Gillis

Gary G. Adams

Arthur J. Rowe

James H.R. Tucker

Anna F.A. Peacock

Paul V. Murphy



Abstract

Scaffold design, synthesis and application are relevant for biomedical research. For example, multivalent interactions, such as those between cell surface glycoproteins and lectins can influence the potency and duration of signalling. The spacing between carbohydrates on their native protein scaffold could be important. Herein, the coiled coil design principle is used to generate synthetic coiled coil type glycoproteins, where three lactose residues are grafted to the coil via N-linkages to asparagine. Molecular modelling indicates that the distance between the galactose anomeric carbon atoms on the neoglycoproteins is ∼30 Å. The inclusion of lactose was accommodated in both the final heptad towards the N-terminus, or more centrally in the penultimate heptad. In either case, neither the helicity nor the assembly to the trimeric form was unduly altered by the presence of the disaccharide.

Citation

Sweeney, S. M., Bullen, G. A., Gillis, R. B., Adams, G. G., Rowe, A. J., Harding, S. E., …Murphy, P. V. (2016). Coiled coil type neoglycoproteins presenting three lactose residues. Tetrahedron Letters, 57(13), doi:10.1016/j.tetlet.2016.02.005

Journal Article Type Article
Acceptance Date Feb 1, 2016
Online Publication Date Feb 6, 2016
Publication Date Mar 30, 2016
Deposit Date May 8, 2017
Journal Tetrahedron Letters
Print ISSN 0040-4039
Electronic ISSN 0040-4039
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 57
Issue 13
DOI https://doi.org/10.1016/j.tetlet.2016.02.005
Keywords Scaffold; Glycosylated; Coiled coil; Glycocluster
Public URL http://eprints.nottingham.ac.uk/id/eprint/42599
Publisher URL http://www.sciencedirect.com/science/article/pii/S0040403916301150
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingham.ac.uk/end_user_agreement.pdf