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

21 October 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We report the synthesis of a library of phospho-amino acid analogues using a novel allyl-phosphoester deprotection strategy. By reacting phenols and alcohols with a combination of POCl3 and allyl alcohol we generate protected phosphoesters that can be subsequently deprotected via treatment with Pd(OAc)2. We go on to show that the generated phosphoserine and phosphotyrosine analogues can be used to generate adhesive calcium phosphate cements with potential applications in the treatment of bone defects. In particular, we use mechanical testing to demonstrate the importance of multiple calcium binding motifs and steric arrangement in promoting adhgesive strength.

Keywords

Biomaterials
phosphoserine
phosphotyrosine
calcium phosphate cement
phosphorylation

Supplementary materials

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Spicer PAA analogues SI
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