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

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

doi:10.1021/acscentsci.9b01149

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

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

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	226-231
Number of pages	6
Journal	ACS Central Science
Volume	6
Issue number	2
DOIs	https://doi.org/10.1021/acscentsci.9b01149
Publication status	Published - 26 Feb 2020

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.

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10.1021/acscentsci.9b01149

Synthesis of Phospho-Amino Acid Analogues as Tissue Adhesive Cement Additives
© 2020 American Chemical Society. This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
Final published version, 1.91 MBLicence: Other

Cite this

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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.",

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AU - Pujari-Palmer, Michael

AU - Autefage, Hélène

AU - Insley, Gerard

AU - Procter, Philip

AU - Engqvist, Håkan

AU - Stevens, Molly M.

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PY - 2020/2/26

Y1 - 2020/2/26

N2 - 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.

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

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

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Research data supporting "Synthesis of phospho-amino acid analogues as tissue adhesive cement additives"

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