823829-27-2Relevant academic research and scientific papers
Acid-sensitive auxiliary assisted atypical diubiquitin synthesis exploiting thiol-ene coupling
Hua, Xiao,Bai, Jing-Si,Kong, Yi-Fu,Chu, Guo-Chao,Shi, Jing,Li, Yi-Ming
, (2019/09/16)
Atypical ubiquitin (Ub) chains are generally involved in intracellular physiological processes, while the molecular mechanisms underlying their regulation remain unclear. In this work, we report an acid-sensitive auxiliary group based bifunctional handle that can prepare Lys27-, Lys29- and Lys33-diUb analogs by thiol-ene coupling (TEC) in combination with native chemical ligation (NCL). A prominent advantage of this method is the rapid and effective removal of acid-sensitive auxiliary groups after the formation of the isopeptide bond mimic. Collectively, this work illustrates the utility of the new strategy in the simple and efficient production of homogeneous atypical diUb analogs for biochemical and biophysical studies.
Chemical Synthesis of Diubiquitin-Based Photoaffinity Probes for Selectively Profiling Ubiquitin-Binding Proteins
Liang, Jun,Zhang, Lin,Tan, Xiang-Long,Qi, Yun-Kun,Feng, Shan,Deng, Haiteng,Yan, Yijing,Zheng, Ji-Shen,Liu, Lei,Tian, Chang-Lin
supporting information, p. 2744 - 2748 (2017/02/26)
Biochemical studies of cellular processes involving polyubiquitin have gained increasing attention. More tools are needed to identify ubiquitin (Ub)-binding proteins. We report diazirine-based photoaffinity probes that can capture Ub-binding proteins in c
Novel prothetic group connecting arm for synthesizing diubiquitin and synthesis method of diubiquitin
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Paragraph 0039; 0041, (2017/10/07)
The invention discloses a novel prothetic group connecting arm for synthesizing diubiquitin and a synthesis method of the diubiquitin. The prothetic group connecting arm disclosed by the invention is loaded on protein through TEC (Triethyl Citrate) reaction and then is coupled with first-section ubiquitin through NCL; finally, a prothetic group is removed to obtain a ubiquitin chain based on a ubiquitin expression unit. According to the method disclosed by the invention, the disadvantage of a former technology that macromolecules are subjected to coupling reaction through TEC and the efficiency is low are overcome, and small molecules and the macromolecules are subjected to efficient reaction; a formed amide bond is closet to a natural isopeptide bond, so that a subsequent biochemical mechanism research is convenient to perform.
New semi-synthesis of ubiquitin C-terminal conjugate with 7-amino-4-methylcoumarin
Li, Yi-Tong,Liang, Jun,Li, Jia-Bin,Fang, Ge-Min,Huang, Yong,Liu, Lei
, p. 102 - 107 (2014/02/14)
The ligation of peptide hydrazides at a Gly site carrying a removal auxiliary was found to be an efficient process. This technology was successfully used for the synthesis of ubiquitin C-terminal conjugates. Recombinant Ub(1-75)-NHNH2 was prepared through the hydrozinolysis of the Ub(1-75)-intein fusion protein. It was ligated with a glycine derivative modified with an acid-sensitive thiol auxiliary. The final acid treatment produced the desired bioactive ubiquitin conjugates in practical quantities. Thus, the method described here extends the protocols of expressed protein ligation. Copyright 2013 European Peptide Society and John Wiley & Sons, Ltd. Native chemical ligation of a recombinant peptide hydrazide with a Gly-peptide carrying a removal auxiliary was examined and used to synthesize ubiquitin C-terminal conjugates. Copyright
Native chemical ubiquitination using a genetically incorporated azidonorleucine
Yang, Renliang,Bi, Xiaobao,Li, Fupeng,Cao, Yuan,Liu, Chuan-Fa
supporting information, p. 7971 - 7974 (2014/07/08)
A robust chemical ubiquitination method was developed. The method employed a genetically incorporated azidonorleucine as an orthogonal lysine precursor for the installation of a Gly residue bearing an Nα-auxiliary which mediated the ligation between ubiquitin(1-75)-thioester and the target protein. To demonstrate our methodology, a model protein, K48-linked diubiquitin, was synthesized with an overall yield of 35%. the Partner Organisations 2014.
Rapid synthesis of acyl transfer auxiliaries for cysteine-free native glycopeptide ligation
Macmillan, Derek,Anderson, David W.
, p. 4659 - 4662 (2007/10/03)
(Chemical Equation Presented) Rapid, facile routes to the TFA-cleavable 4,5,6-trimethoxy-2-mercaptobenzyl and 1-(2,4-dimethoxyphenyl)-2-mercaptoethyl classes of auxiliaries for cysteine-free native chemical ligation are described. Rapid synthesis, coupled
