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

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.

SUBMITTER: Spicer CD

PROVIDER: S-EPMC7047273 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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

Spicer Christopher D CD Pujari-Palmer Michael M Autefage Hélène H Insley Gerard G Procter Philip P Engqvist Håkan H Stevens Molly M MM

ACS central science 20200211 2

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 ...[more]

PMID: 32123740

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