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

Christopher D. Spicer | Zendy; Michael PujariPalmer | Zendy; Hélène Autefage | Zendy; Gerard Insley | Zendy; Philip Procter | Zendy; Håkan Engqvist | Zendy; Molly M. Stevens | Zendy

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

Author(s) -

Christopher D. Spicer,

Michael PujariPalmer,

Hélène Autefage,

Gerard Insley,

Philip Procter,

Håkan Engqvist,

Molly M. Stevens

Publication year - 2020

Publication title -

acs central science

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 4.893

H-Index - 76

eISSN - 2374-7951

pISSN - 2374-7943

DOI - 10.1021/acscentsci.9b01149

Subject(s) - phosphodiester bond , phosphoserine , chemistry , adhesion , adhesive , amino acid , substrate (aquarium) , calcium phosphate cement , phosphate , calcium , combinatorial chemistry , stereochemistry , biochemistry , organic chemistry , phosphorylation , serine , biology , ecology , rna , layer (electronics) , gene

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.

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