Citation: Wu Ye, Li Yulei, Cong Wei, Zou Yan, Li Xiang, Hu Honggang. Total synthesis of TRADD death domain with arginine N-GlcNAcylation by hydrazide-based native chemical ligation[J]. Chinese Chemical Letters, ;2020, 31(1): 107-110. doi: 10.1016/j.cclet.2019.05.010 shu

Total synthesis of TRADD death domain with arginine N-GlcNAcylation by hydrazide-based native chemical ligation

Wu Ye ^a,b ,
Li Yulei ^c,1 ,
Cong Wei ^a ,
Zou Yan ^b ,
Li Xiang ^b,*, ,
Hu Honggang ^a,*,

a.
Institute of Translational Medicine, Shanghai University, Shanghai 200436, China
b.
School of Pharmacy, Second Military Medical University, Shanghai 200433, China
c.
Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China

xiangli@smmu.edu.cn

hhu66@shu.edu.cn

Received Date: 26 March 2019
Revised Date: 18 April 2019
Accepted Date: 6 May 2019
Available Online: 8 January 2019

Figures(4)

TNFR1-associated death domain protein (TRADD) with arginine N-GlcNAcylation is a novel and structurally unique posttranslational modification (PTM) glycoprotein that blocks the formation of death-inducing signaling complex (DISC), orchestrating host nuclear factor kB (NF-kB) signaling in entero-pathogenic Escherichia coli (EPEC)-infected cells. This particular glycosylated modification plays an extremely vital role for the effective colonization and pathogenesis of pathogens in the gut. Herein we describe the total synthesis of TRADD death domain (residues 195-312) with arginine235 N-GlcNAcylation (Arg-GlcNAc TRADD (195-312)). Two longish peptidyl fragments of the wild-type primary sequence were obtained by robust, microwave-assisted, highly efficient, solid-phase peptide synthesis (SPPS), the N-GlcNAcylated sector was built by total synthesis and attached specifically to resinbound peptide with an unprotected ornithine residue via silver-promoted on-resin guanidinylation, Arg-GlcNAc TRADD (195-312) was constructed by hydrazide-based native chemical ligation (NCL). The facile synthetic strategy is expected to be generally applicable for the rapid synthesis of other proteins with Arg-GlcNAc modification and to pave the way for the related chemically biological study.
- TRADD death domain,
- Posttranslational modification,
- Protein chemical synthesis,
- Solid-phase peptide synthesis,
- Native chemical ligation,
- Peptide hydrazide
1. [1]
  K. Ohtsubo, J.D. Marth, Cell 126 (2006) 855-867. doi: 10.1016/j.cell.2006.08.019
2. [2]
  D.J. Gill, H. Clausen, F. Bard, Trends. Cell. Biol. 21 (2011) 149-158. doi: 10.1016/j.tcb.2010.11.004
3. [3]
  K.W. Moremen, M. Tiemeyer, A.V. Nairn, Nat. Rev. Mol. Cell. Biol. 13 (2012) 448-462.
4. [4]
  J. Lassak, E.C. Keilhauer, M. Furst, et al., Nat. Chem. Biol. 11 (2015) 266-270. doi: 10.1038/nchembio.1751
5. [5]
  J. Qiu, M.J. Sheedlo, K. Yu, et al., Nature 533 (2016) 120-124. doi: 10.1038/nature17657
6. [6]
  P. Zhou, Y. She, N. Dong, et al., Nature 561 (2018) 122-126. doi: 10.1038/s41586-018-0433-3
7. [7]
  D.G. Singh, J. Lomako, W.M. Lomako, et al., FEBS Lett. 376 (1995) 61-64. doi: 10.1016/0014-5793(95)01247-6
8. [8]
  S. Li, L. Zhang, Q. Yao, et al., Nature 501 (2013) 242-246. doi: 10.1038/nature12436
9. [9]
  J.S. Pearson, C. Giogha, S.Y. Ong, et al., Nature 501 (2013) 247-251. doi: 10.1038/nature12524
10. [10]
  M. Pan, S. Li, X. Li, et al., Angew. Chem. Int. Ed. 53 (2014) 14517-14521. doi: 10.1002/anie.201407824
11. [11]
  Q. Qu, M. Pan, S. Gao, et al., Adv. Sci. 5 (2018) 1800234. doi: 10.1002/advs.201800234
12. [12]
  M. Pan, S. Gao, Y. Zheng, et al., J. Am. Chem. Soc. 138 (2016) 7429-7435. doi: 10.1021/jacs.6b04031
13. [13]
  X. Li, R. Krafczyk, J. Macosek, et al., Chem. Sci. 7 (2016) 6995-7001. doi: 10.1039/C6SC02889F
14. [14]
  P.E. Dawson, T.W. Muir, I. Clark-Lewis, et al., Science 266 (1994) 776-779. doi: 10.1126/science.7973629
15. [15]
  A.C. Conibear, E.E. Watson, R.J. Payne, et al., Chem. Soc. Rev. 47 (2018) 9046-9068. doi: 10.1039/C8CS00573G
16. [16]
  S.S. Kulkarni, J. Sayers, B. Premdjee, et al., Nat. Rev. Chem. 2 (2018) 0122. doi: 10.1038/s41570-018-0122
17. [17]
  B. Yan, W. Shi, L. Ye, et al., Curr. Opin. Chem. Biol. 46 (2018) 33-40. doi: 10.1016/j.cbpa.2018.03.018
18. [18]
  G.M. Fang, J.X. Wang, L. Liu, et al., Angew. Chem. Int. Ed. 51 (2012) 10347-10350. doi: 10.1002/anie.201203843
19. [19]
  J.S. Zheng, S. Tang, Y.K. Qi, et al., Nat. Protoc. 8 (2013) 2483-2495. doi: 10.1038/nprot.2013.152
20. [20]
  Y.C. Huang, G.M. Fang, L. Liu, et al., Natl. Sci. Rev. 3 (2016) 107-116. doi: 10.1093/nsr/nwv072
21. [21]
  G.M. Fang, Y.M. Li, F. Shen, et al., Angew. Chem. Int. Ed. 50 (2011) 7645-7649. doi: 10.1002/anie.201100996
22. [22]
  Z.M. Wang, W.L. Xu, L. Liu, et al., Nat. Chem. 8 (2016) 698-704. doi: 10.1038/nchem.2517
23. [23]
  J.S. Zheng, M. Yu, Y.K. Qi, et al., J. Am. Chem. Soc. 136 (2014) 3695-3704. doi: 10.1021/ja500222u
24. [24]
  S. Wang, L. Corcilius, P.P. Sharp, et al., Bioorg. Med. Chem. 25 (2017) 2895-2900. doi: 10.1016/j.bmc.2017.03.012
25. [25]
  Y. Wu, Y.H. Li, X. Li, et al., Chem. Sci. 8 (2017) 7368-7373. doi: 10.1039/C7SC02420G
26. [26]
  X. Li, W.D. Tolbert, H.G. Hu, et al., Chem. Sci. 10 (2019) 1522-1530. doi: 10.1039/C8SC03275K
27. [27]
  U. Carlo, K. Yasuhiro, Curr. Opin. Chem. Biol. 46 (2018) 130-137.
1. [1]
  Ying Li , Long-Jie Wang , Yong-Kang Zhou , Jun Liang , Bin Xiao , Ji-Shen Zheng . An improved installation of 2-hydroxy-4-methoxybenzyl (iHmb) method for chemical protein synthesis. Chinese Chemical Letters, 2024, 35(5): 109033-. doi: 10.1016/j.cclet.2023.109033
2. [2]
  Min Fu , Pan He , Sen Zhou , Wenqiang Liu , Bo Ma , Shiying Shang , Yaohao Li , Ruihan Wang , Zhongping Tan . An unexpected stereochemical effect of thio-substituted Asp in native chemical ligation. Chinese Chemical Letters, 2024, 35(8): 109434-. doi: 10.1016/j.cclet.2023.109434
3. [3]
  Xu-Hui Yue , Xiang-Wen Zhang , Hui-Min He , Lei Qiao , Zhong-Ming Sun . Synthesis, chemical bonding and reactivity of new medium-sized polyarsenides. Chinese Chemical Letters, 2024, 35(7): 108907-. doi: 10.1016/j.cclet.2023.108907
4. [4]
  Jianhui Yin , Wenjing Huang , Changyong Guo , Chao Liu , Fei Gao , Honggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244
5. [5]
  Jian Li , Jinjin Chen , Qi-Long Hu , Zhen Wang , Xiao-Feng Xiong . Recent progress of chemical methods for lysine site-selective modification of peptides and proteins. Chinese Chemical Letters, 2025, 36(5): 110126-. doi: 10.1016/j.cclet.2024.110126
6. [6]
  Wenbi Wu , Yinchu Dong , Haofan Liu , Xuebing Jiang , Li Li , Yi Zhang , Maling Gou . Modification of plasma protein for bioprinting via photopolymerization. Chinese Chemical Letters, 2024, 35(8): 109260-. doi: 10.1016/j.cclet.2023.109260
7. [7]
  Jingyu Shi , Xiaofeng Wu , Yutong Chen , Yi Zhang , Xiangyan Hou , Ruike Lv , Junwei Liu , Mengpei Jiang , Keke Huang , Shouhua Feng . Structure factors dictate the ionic conductivity and chemical stability for cubic garnet-based solid-state electrolyte. Chinese Chemical Letters, 2025, 36(5): 109938-. doi: 10.1016/j.cclet.2024.109938
8. [8]
  Weiyu Chen , Zenghui Li , Chenguang Zhao , Lisha Zha , Junfeng Shi , Dan Yuan . Enzyme-modulate conformational changes in amphiphile peptide for selectively cell delivery. Chinese Chemical Letters, 2024, 35(12): 109628-. doi: 10.1016/j.cclet.2024.109628
9. [9]
  Xiaofang Luo , Ye Wu , Xiaokun Zhang , Min Tang , Feiye Ju , Zuodong Qin , Gregory J Duns , Wei-Dong Zhang , Jiang-Jiang Qin , Xin Luan . Peptide-based strategies for overcoming multidrug-resistance in cancer therapy. Chinese Chemical Letters, 2025, 36(1): 109724-. doi: 10.1016/j.cclet.2024.109724
10. [10]
  Shu-Ran Xu , Fang-Xing Xiao . Metal halide perovskites quantum dots: Synthesis, and modification strategies for solar CO2 conversion. Chinese Journal of Structural Chemistry, 2023, 42(12): 100173-100173. doi: 10.1016/j.cjsc.2023.100173
11. [11]
  Xueling Yu , Lixing Fu , Tong Wang , Zhixin Liu , Na Niu , Ligang Chen . Multivariate chemical analysis: From sensors to sensor arrays. Chinese Chemical Letters, 2024, 35(7): 109167-. doi: 10.1016/j.cclet.2023.109167
12. [12]
  Tiantian Long , Hongmei Luo , Jingbo Sun , Fengniu Lu , Yi Chen , Dong Xu , Zhiqin Yuan . Carbonization-engineered ultrafast chemical reaction on nanointerface. Chinese Chemical Letters, 2025, 36(3): 109728-. doi: 10.1016/j.cclet.2024.109728
13. [13]
  Rui Wang , He Qi , Haijiao Zheng , Qiong Jia . Light/pH dual-responsive magnetic metal-organic frameworks composites for phosphorylated peptide enrichment. Chinese Chemical Letters, 2024, 35(7): 109215-. doi: 10.1016/j.cclet.2023.109215
14. [14]
  Cheng-Yan Wu , Yi-Nan Gao , Zi-Han Zhang , Rui Liu , Quan Tang , Zhong-Lin Lu . Enhancing self-assembly efficiency of macrocyclic compound into nanotubes by introducing double peptide linkages. Chinese Chemical Letters, 2024, 35(11): 109649-. doi: 10.1016/j.cclet.2024.109649
15. [15]
  Shaofeng Gong , Zi-Wei Deng , Chao Wu , Wei-Min He . Stabilized carbon radical-mediated three-component functionalization of amino acid/peptide derivatives. Chinese Chemical Letters, 2025, 36(5): 110936-. doi: 10.1016/j.cclet.2025.110936
16. [16]
  Chaochao Jin , Kai Li , Jiongpei Zhang , Zhihua Wang , Jiajing Tan . N,O-Bidentated difluoroboron complexes based on pyridine-ester enolates: Facile synthesis, post-complexation modification, optical properties, and applications. Chinese Chemical Letters, 2024, 35(9): 109532-. doi: 10.1016/j.cclet.2024.109532
17. [17]
  Chuanfeng Fan , Jian Gao , Yingkai Gao , Xintong Yang , Gaoning Li , Xiaochun Wang , Fei Li , Jin Zhou , Haifeng Yu , Yi Huang , Jin Chen , Yingying Shan , Li Chen . A non-peptide-based chymotrypsin-targeted long-wavelength emission fluorescent probe with large Stokes shift and its application in bioimaging. Chinese Chemical Letters, 2024, 35(10): 109838-. doi: 10.1016/j.cclet.2024.109838
18. [18]
  Xianxu Chu , Lu Wang , Junru Li , Hui Xu . Surface chemical microenvironment engineering of catalysts by organic molecules for boosting electrocatalytic reaction. Chinese Chemical Letters, 2024, 35(8): 109105-. doi: 10.1016/j.cclet.2023.109105
19. [19]
  Ali Dai , Zhiguo Zheng , Liusheng Duan , Jian Wu , Weiming Tan . Small molecule chemical scaffolds in plant growth regulators for the development of agrochemicals. Chinese Chemical Letters, 2025, 36(4): 110462-. doi: 10.1016/j.cclet.2024.110462
20. [20]
  Ning Zhang , Mengjie Qin , Jiawen Zhu , Xuejing Lou , Xiao Tian , Wende Ma , Youmei Wang , Minghua Lu , Zongwei Cai . Thickness-controllable synthesis of metal-organic framework based hollow nanoflowers with magnetic core via liquid phase epitaxy for phosphopeptides enrichment. Chinese Chemical Letters, 2025, 36(4): 110177-. doi: 10.1016/j.cclet.2024.110177

Get Citation

PDF

XML

Metrics

PDF Downloads(9)
Abstract views(1046)
HTML views(92)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142