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邻氨基苯甲酸，芳香族残基标记前体化合物组合中的新成员。

Anthranilic acid, the new player in the ensemble of aromatic residue labeling precursor compounds.

作者信息

Schörghuber Julia, Geist Leonhard, Bisaccia Marilena, Weber Frederik, Konrat Robert, Lichtenecker Roman J

机构信息

Institute of Organic Chemistry, University of Vienna, Währingerstr. 38, 1090, Vienna, Austria.

Christian Doppler Laboratory for High-Content Structural Biology and Biotechnology, Department of Structural and Computational Biology, Max F. Perutz Laboratories, University of Vienna, Dr-Bohr-Gasse 9, 1030, Vienna, Austria.

出版信息

J Biomol NMR. 2017 Sep;69(1):13-22. doi: 10.1007/s10858-017-0129-2. Epub 2017 Aug 31.

DOI:10.1007/s10858-017-0129-2
PMID:28861670
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5626795/
Abstract

The application of metabolic precursors for selective stable isotope labeling of aromatic residues in cell-based protein overexpression has already resulted in numerous NMR probes to study the structural and dynamic characteristics of proteins. With anthranilic acid, we present the structurally simplest precursor for exclusive tryptophan side chain labeling. A synthetic route to C, H isotopologues allows the installation of isolated C-H spin systems in the indole ring of tryptophan, representing a versatile tool to investigate side chain motion using relaxation-based experiments without the loss of magnetization due to strong J and weaker J scalar couplings, as well as dipolar interactions with remote hydrogens. In this article, we want to introduce this novel precursor in the context of hitherto existing techniques of in vivo aromatic residue labeling.

摘要

代谢前体在基于细胞的蛋白质过表达中用于芳香族残基的选择性稳定同位素标记，这已经产生了许多用于研究蛋白质结构和动力学特征的核磁共振（NMR）探针。利用邻氨基苯甲酸，我们提出了用于色氨酸侧链专一性标记的结构最简单的前体。一条合成C、H同位素异构体的路线能够在色氨酸的吲哚环中安装孤立的C-H自旋系统，这是一种通用工具，可用于通过基于弛豫的实验研究侧链运动，而不会因强J和较弱的J标量耦合以及与远程氢的偶极相互作用而导致磁化强度损失。在本文中，我们想在迄今已有的体内芳香族残基标记技术背景下介绍这种新型前体。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/106b/5626795/abc100545b82/10858_2017_129_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/106b/5626795/236e66e4cdb8/10858_2017_129_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/106b/5626795/0251bd73e15d/10858_2017_129_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/106b/5626795/16c0b016bb6b/10858_2017_129_Sch3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/106b/5626795/c6242cfd3933/10858_2017_129_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/106b/5626795/65ab52b98d3b/10858_2017_129_Sch4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/106b/5626795/170002fec05b/10858_2017_129_Sch5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/106b/5626795/04b523498955/10858_2017_129_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/106b/5626795/abc100545b82/10858_2017_129_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/106b/5626795/236e66e4cdb8/10858_2017_129_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/106b/5626795/0251bd73e15d/10858_2017_129_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/106b/5626795/16c0b016bb6b/10858_2017_129_Sch3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/106b/5626795/c6242cfd3933/10858_2017_129_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/106b/5626795/65ab52b98d3b/10858_2017_129_Sch4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/106b/5626795/170002fec05b/10858_2017_129_Sch5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/106b/5626795/04b523498955/10858_2017_129_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/106b/5626795/abc100545b82/10858_2017_129_Fig3_HTML.jpg

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