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Synthesis of Phospho-Amino Acid Analogues as Tissue Adhesive Cement Additives.
ACS Central Science ( IF 18.2 ) Pub Date : 2020-02-11 , DOI: 10.1021/acscentsci.9b01149
Christopher D Spicer 1, 2, 3 , Michael Pujari-Palmer 4 , Hélène Autefage 1 , Gerard Insley 4 , Philip Procter 4 , Håkan Engqvist 4 , Molly M Stevens 1, 5
Affiliation  

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.

中文翻译:

磷酸氨基酸类似物的合成作为组织粘合剂水泥添加剂。

在本文中,我们报告了通过新颖的单步烯丙基磷酸酯保护/ Pd介导的脱保护策略合成磷酸氨基酸类似物的文库。然后将这些磷酸丝氨酸和磷酸酪氨酸类似物用作添加剂,以产生粘性磷酸钙粘固剂,从而使我们能够探索表面结合强度提高的化学来源。我们证明了多种钙结合基序在介导粘附中的重要性,并突出了底物疏水性和取向在控制结合强度中所起的关键作用。
更新日期:2020-02-26
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