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氟磷酸重氮苯(formylbenzene diazonium hexafluorophosphate)试剂用于酪氨酸选择性修饰蛋白质,并引入生物正交醛基。

Formylbenzene diazonium hexafluorophosphate reagent for tyrosine-selective modification of proteins and the introduction of a bioorthogonal aldehyde.

机构信息

Departments of Chemistry and Molecular Biology, The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Rd., La Jolla, CA 92037, USA.

出版信息

Bioconjug Chem. 2012 Dec 19;23(12):2321-8. doi: 10.1021/bc300410p. Epub 2012 Nov 29.

Abstract

4-Formylbenzene diazonium hexafluorophosphate (FBDP) is a novel bench-stable crystalline diazonium salt that reacts selectively with tyrosine to install a bioorthogonal aldehyde functionality. Model studies with N-acyl-tyrosine methylamide allowed us to identify conditions optimal for tyrosine ligation reactions with small peptides and proteins. FBDP-based conjugation was used for the facile introduction of small molecule tags, poly(ethylene glycol) chains (PEGylation), and functional small molecules onto model proteins and to label the surface of living cells.

摘要

4-甲酰基苯重氮六氟磷酸盐(FBDP)是一种新型的、稳定的晶体重氮盐,它能选择性地与酪氨酸反应,引入一个生物正交的醛基官能团。通过对 N-酰基-酪氨酸甲酯的模型研究,我们确定了与小肽和蛋白质进行酪氨酸连接反应的最佳条件。基于 FBDP 的偶联反应可用于将小分子标签、聚乙二醇(PEGylation)链和功能小分子轻松地引入到模型蛋白中,并对活细胞的表面进行标记。

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