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

preprint
submitted on 15.10.2019, 11:27 and posted on 21.10.2019, 16:28 by Christopher Spicer, Michael Pujari-Palmer, Hélène Autefage, Gerard Insley, Philip Procter, Håkan Engqvist, Molly Stevens
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.

Funding

SSF 4-3713/2296 2016

Ulla och Gustaf af Ugglas Stiftelse

History

Email Address of Submitting Author

chris.spicer@york.ac.uk

Institution

University of York

Country

UK

ORCID For Submitting Author

0000-0001-8787-578X

Declaration of Conflict of Interest

M.P.-P., G.I., P.P., and H.E. declare partial ownership in a company that owns intellectual property related to PSer containing CPCs, GPBio LTD.

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