Synthesis of Phospho-Amino Acid Analogues as Tissue Adhesive Cement Additives

By the same authors

Tuneable peptide cross-linked nanogels for enzyme-triggered protein delivery
Massi, L., Najer, A., Chapman, R., Spicer, C. D., Nele, V., Che, J., Booth, M. A., Doutch, J. J. & Stevens, M. M., 14 Oct 2020
Article in Journal of Materials Chemistry B
Photochemical Methods for Peptide Macrocylization
Raynal, L., Rose, N. C., Donald, J. R. & Spicer, C., 11 Sep 2020
Article in Chemistry : A European Journal
An Electroactive Oligo-EDOT Platform for Neural Tissue Engineering
Ritzau-Reid, K. I., Spicer, C. D., Gelmi, A., Grigsby, C. L., Ponder, J. F., Bemmer, V., Creamer, A., Vilar, R., Serio, A. & Stevens, M. M., 14 Aug 2020
Article in ADVANCED FUNCTIONAL MATERIALS
Hydrogel scaffolds for tissue engineering: The importance of polymer choice
Spicer, C. D., 25 Sep 2019
Review article in Polymer Chemistry
Shape-controlled synthesis and in situ characterisation of anisotropic Au nanomaterials using liquid cell transmission electron microscopy
Wang, S-T., Lin, Y., Nielsen, M. H., Song, C. Y., Thomas, M. R., Spicer, C. D., Kröger, R., Ercius, P., Aloni, S. & Stevens, M. M., 30 Aug 2019
Article in Nanoscale

From the same journal

An epoxide intermediate in glycosidase catalysis
Sobala, L. F., Speciale, G., Zhu, S., Raich, L., Sannikova, N., Thompson, A. J., Hakki, Z., Lu, D., Abadi, S. S. K., Lewis, A. R., Rojas-Cervellera, V., Bernardo-Seisdedos, G., Zhang, Y., Millet, O., Jiménez-Barbero, J., Bennet, A. J., Sollogoub, M., Rovira, C., Davies, G. J. & Williams, S. J., 27 May 2020
Article in ACS Central Science
Dynamic and Functional Profiling of Xylan-Degrading Enzymes in Aspergillus Secretomes Using Activity-Based Probes
Schröder, S. P., De Boer, C., McGregor, N. G. S., Rowland, R. J., Moroz, O., Blagova, E., Reijngoud, J., Arentshorst, M., Osborn, D., Morant, M. D., Abbate, E., Stringer, M. A., Krogh, K. B. R. M., Raich, L., Rovira, C., Berrin, J. G., Van Wezel, G. P., Ram, A. F. J., Florea, B. I., Van Der Marel, G. A. & 5 others, Codée, J. D. C., Wilson, K. S., Wu, L., Davies, G. J. & Overkleeft, H. S., 26 Jun 2019
Article in ACS Central Science
On Biomineralization: Enzymes Switch on Mesocrystal Assembly
Rao, A., Roncal-Herrero, T., Schmid, E., Drechsler, M., Scheffner, M., Gebauer, D., Kröger, R. & Cölfen, H., 27 Feb 2019
Article in ACS Central Science
Structural and biochemical insights into the function and evolution of sulfoquinovosidases
Abayakoon, P., Jin, Y., Lingford, J. P., Petricevic, M., John, A., Ryan, E., Pires, D. E. V., Ascher, D. B., Davies, G. J., Goddard-Borger, E. D. & Williams, S. J., 26 Sep 2018
Article in ACS Central Science

From the same journal

ACS Central Science (Journal)
Gideon John Davies (Editorial board member)
2020
Activity: Publication peer-review and editorial work › Editorial board
ACS Central Science (Journal)
Gideon John Davies (Editorial board member)
2019
Activity: Publication peer-review and editorial work › Editorial board
ACS Central Science (Journal)
Gideon John Davies (Editorial board member)
2018
Activity: Publication peer-review and editorial work › Editorial board
ACS Central Science (Journal)
Gideon John Davies (Editorial board member)
2017
Activity: Publication peer-review and editorial work › Editorial board

Research output: Contribution to journal › Article

Full text download(s)

Synthesis of Phospho-Amino Acid Analogues as Tissue Adhesive Cement Additives
1.91 MB, PDF document

Published copy (DOI)

10.1021/acscentsci.9b01149

Author(s)

Christopher D. Spicer
Michael Pujari-Palmer
Hélène Autefage
Gerard Insley
Philip Procter
Håkan Engqvist
Molly M. Stevens

Department/unit(s)

Chemistry

Publication details

Journal	ACS Central Science
Date	Accepted/In press - 28 Jan 2020
Date	Published (current) - 26 Feb 2020
Issue number	2
Volume	6
Number of pages	6
Pages (from-to)	226-231
Original language	English

Abstract

In this paper we report the synthesis of a library of phospho-amino acid analogues, via a novel single-step allyl-phosphoester protection/Pd-mediated deprotection strategy. These phosphoserine and phosphotyrosine analogues were then applied as additives to create adhesive calcium phosphate cements, allowing us to probe the chemical origins of the increased surface binding strength. We demonstrate the importance of multiple calcium binding motifs in mediating adhesion, as well as highlighting the crucial role played by substrate hydrophobicity and orientation in controlling binding strength.

Bibliographical note

© 2020 American Chemical Society. This is an open access article published under an ACS Author Choice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.

Discover related content

Find related publications, people, projects, datasets and more using interactive charts.

View graph of relations

York staff: edit these data

The York Research Database

By the same authors

From the same journal

From the same journal