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

[Image: see text] 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 p...

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Detalles Bibliográficos
Autores principales: Spicer, Christopher D., Pujari-Palmer, Michael, Autefage, Hélène, Insley, Gerard, Procter, Philip, Engqvist, Håkan, Stevens, Molly M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7047273/
https://www.ncbi.nlm.nih.gov/pubmed/32123740
http://dx.doi.org/10.1021/acscentsci.9b01149
Descripción
Sumario:[Image: see text] 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.