Genetically Encoded 2-Aryl-5-carboxytetrazoles for Site-Selective Protein Photo-Cross-Linking

Journal of the American Chemical Society
Yulin TianQing Lin

Abstract

The genetically encoded photo-cross-linkers promise to offer a temporally controlled tool to map transient and dynamic protein-protein interaction complexes in living cells. Here we report the synthesis of a panel of 2-aryl-5-carboxytetrazole-lysine analogs (ACTKs) and their site-specific incorporation into proteins via amber codon suppression in Escherichia coli and mammalian cells. Among five ACTKs investigated, N-methylpyrroletetrazole-lysine (mPyTK) was found to give robust and site-selective photo-cross-linking reactivity in E. coli when placed at an appropriate site at the protein interaction interface. A comparison study indicated that mPyTK exhibits higher photo-cross-linking efficiency than a diazirine-based photo-cross-linker, AbK, when placed at the same location of the interaction interface in vitro. When mPyTK was introduced into the adapter protein Grb2, it enabled the photocapture of EGFR in a stimulus-dependent manner. The design of mPyTK along with the identification of its cognate aminoacyl-tRNA synthetase makes it possible to map transient protein-protein interactions and their interfaces in living cells.

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Citations

Aug 26, 2018·Angewandte Chemie·Tuan-Anh NguyenKathrin Lang
May 17, 2019·Essays in Biochemistry·Alexander R NödlingYu-Hsuan Tsai
Aug 19, 2020·Chemical Communications : Chem Comm·R David RowJennifer A Prescher
Jul 14, 2020·Biochemical Society Transactions·Haiyan Ren
Oct 5, 2019·Chemistry : a European Journal·Laura Ortiz-RojanoMaria Ribagorda
Feb 29, 2020·Chemical Communications : Chem Comm·Shana WagnerKabirul Islam
Apr 14, 2018·Chemical Communications : Chem Comm·Yulin Tian, Qing Lin
Feb 29, 2020·Chemical Science·Keith LivingstoneCraig Jamieson
Sep 2, 2020·Journal of the American Chemical Society·Sheng-Yao Dai, Dan Yang
Apr 5, 2021·Current Opinion in Microbiology·Hao ChenChenguang Fan
Apr 21, 2021·Journal of the American Chemical Society·Alexander V WestChristina M Woo
Apr 22, 2018·Journal of the American Society for Mass Spectrometry·Claudio IacobucciAndrea Sinz
Sep 2, 2017·Organic Letters·Kenji MishiroMunetaka Kunishima
Sep 28, 2018·The Journal of Organic Chemistry·Kenji MishiroMunetaka Kunishima
Jun 12, 2019·Journal of the American Chemical Society·Jun LiuLei Wang
Oct 24, 2018·Journal of the American Chemical Society·Jinbo LiYan Zhang
Nov 4, 2020·Journal of the American Chemical Society·Weijun GuiZhihao Zhuang
Sep 8, 2021·Chemical Communications : Chem Comm·Anirban RoyBabu Sudhamalla
Nov 12, 2021·Protein Science : a Publication of the Protein Society·Li Cao, Lei Wang

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Methods Mentioned

BETA
acylation
affinity purification
nucleotide exchange

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