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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.

DOI:10.1021/bc300410p
PMID:23181702
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3526679/
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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Bioconjug Chem. 2012 Dec 19;23(12):2321-8. doi: 10.1021/bc300410p. Epub 2012 Nov 29.
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本文引用的文献

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Direct peptide bioconjugation/PEGylation at tyrosine with linear and branched polymeric diazonium salts.线性和支化聚合物重氮盐在酪氨酸上的直接肽键连接/聚乙二醇化。
J Am Chem Soc. 2012 May 2;134(17):7406-13. doi: 10.1021/ja211855q. Epub 2012 Apr 21.
2
Characterization of a high-affinity human antibody with a disulfide bridge in the third complementarity-determining region of the heavy chain.鉴定重链第三个互补决定区带有二硫键的高亲和力人源抗体。
J Mol Recognit. 2012 Mar;25(3):125-35. doi: 10.1002/jmr.1168.
3
Synthesis of heterobifunctional protein fusions using copper-free click chemistry and the aldehyde tag.使用无铜点击化学和醛标签合成异双功能蛋白融合体。
Angew Chem Int Ed Engl. 2012 Apr 23;51(17):4161-5. doi: 10.1002/anie.201108130. Epub 2012 Mar 12.
4
Metal-free, visible-light-mediated direct C-H arylation of heteroarenes with aryl diazonium salts.无金属、可见光促进的杂芳烃与芳基重氮盐的直接 C-H 芳基化反应。
J Am Chem Soc. 2012 Feb 15;134(6):2958-61. doi: 10.1021/ja212099r. Epub 2012 Feb 3.
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Detection of cellular sialic acid content using nitrobenzoxadiazole carbonyl-reactive chromophores.利用硝酮羰基反应性生色团检测细胞唾液酸含量。
Bioconjug Chem. 2012 Mar 21;23(3):363-71. doi: 10.1021/bc200276k. Epub 2012 Feb 21.
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Tyrosine-targeted spin labeling and EPR spectroscopy: an alternative strategy for studying structural transitions in proteins.酪氨酸靶向自旋标记与电子顺磁共振波谱:研究蛋白质结构转变的一种替代策略。
Angew Chem Int Ed Engl. 2011 Sep 19;50(39):9108-11. doi: 10.1002/anie.201102539. Epub 2011 Aug 24.
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Protein glycoengineering enabled by the versatile synthesis of aminooxy glycans and the genetically encoded aldehyde tag.通过通用的氨基氧基聚糖合成和遗传编码醛标签实现的蛋白质糖基工程化。
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