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

2020; American Chemical Society; Volume: 6; Issue: 2 Linguagem: Inglês

10.1021/acscentsci.9b01149

2374-7951

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

Oral and gingival health research

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.