Formylbenzene Diazonium Hexafluorophosphate Reagent for Tyrosine-Selective Modification of Proteins and the Introduction of a Bioorthogonal Aldehyde

被引：90

作者：

Gavrilyuk, Julia

Ban, Hitoshi

Nagano, Masanobu

Hakamata, Wataru

Barbas, Carlos F., III ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

来源：

BIOCONJUGATE CHEMISTRY | 2012年 / 23卷 / 12期

基金：

美国国家卫生研究院;

关键词：

SURFACE MODIFICATION; HUMAN-ANTIBODY; CHEMISTRY; BIOCONJUGATION; SALTS;

D O I：

10.1021/bc300410p

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

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收藏

页码：2321 / 2328

页数：8

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