Progress in Synthesis of Thiopeptide Antibiotics Analogues
- Corresponding author: Wang Shoufeng, chm_wangsf@ujn.edu.cn Liu wen, wliu@sioc.ac.cn
Citation:
Wang Shoufeng, Zheng Qingfei, Duan Panpan, Liu wen. Progress in Synthesis of Thiopeptide Antibiotics Analogues[J]. Chinese Journal of Organic Chemistry,
;2017, 37(7): 1653-1666.
doi:
10.6023/cjoc201702017
Bagley, M. C.; Dale, J. W.; Merritt, E. A.; Xiong, X. Chem. Rev. 2005, 105, 685.
doi: 10.1021/cr0300441
Li, C.; Kelly, W. L. Nat. Prod. Rep. 2010, 27, 153.
doi: 10.1039/B922434C
Hensens, O. D.; Albers-Schönberg, G. Tetrahedron Lett. 1978, 19, 3649.
Naidu, B. N.; Sorenson, M. E.; Zhang, Y.; Kim, O. K.; Matiskella, J. D.; Wichtowski, J. A.; Connolly, T. P.; Li, W.; Lam, K. S.; Bronson, J. J.; Pucci, M. J.; Clark, J. M.; Ueda, Y. Bioorg. Med. Chem. Lett. 2004, 14, 5573.
doi: 10.1016/j.bmcl.2004.08.058
Zhang, C.; Herath, K.; Jayasuriya, H.; Ondeyka, J. G.; Zink, D. L.; Occi, J.; Birdsall, G.; Venugopal, J.; Ushio, M.; Burgess, B.; Masurekar, P.; Barrett, J. F.; Singh, S. B. J. Nat. Prod. 2009, 72, 841.
doi: 10.1021/np800783b
Zhang, C.; Occi, J.; Masurekar, P.; Barrett, J. F.; Zink, D. L.; Smith, S.; Onishi, R.; Ha, S.; Salazar, O.; Genilloud, O.; Basilio, A.; Vicente, F.; Gill, C.; Hickey, E. J.; Dorso, K.; Motyl. M.; Singh, S. B. J. Am. Chem. Soc. 2008, 130, 12102.
doi: 10.1021/ja803183u
Bower, J.; Drysdale, M.; Hebdon, R.; Jordan, A.; Lentzen, G.; Matassova, N.; Murchie, A.; Powles, J.; Roughley, S. Bioorg. Med. Chem. Lett. 2003, 13, 2455.
doi: 10.1016/S0960-894X(03)00495-5
Naidu, B. N.; Sorenson, M. E.; Bronson, J. J.; Pucci, M. J.; Clark, J. M.; Ueda, Y. Bioorg. Med. Chem. Lett. 2005, 15, 2069.
doi: 10.1016/j.bmcl.2005.02.046
Naidu, B. N.; Sorenson, M. E.; Matiskella, J. D.; Li, W.; Sausker, J. B.; Zhang, Y.; Connolly, T. P.; Lam, K. S.; Bronson, J. J.; Pucci, M. J.; Yang, H.; Ueda, Y. Bioorg. Med. Chem. Lett. 2006, 16, 3545.
doi: 10.1016/j.bmcl.2006.03.079
Regueiro-Ren, A.; Ueda, Y. J. Org. Chem. 2002, 67, 8699.
doi: 10.1021/jo0261698
Connolly, T. P.; Regueiro-Ren, A.; Leet, J. E.; Springer, D. M.; Goodrich, J.; Huang, X.; Pucci, M. J.; Clark, J. M.; Bronson, J. J.; Ueda, Y. J. Nat. Prod. 2005, 68, 550.
doi: 10.1021/np040225d
Xu, L.; Farthing, A. K.; Shi, Y.; Meinke, P. T.; Liu, K. J. Org. Chem. 2007, 72, 7447.
doi: 10.1021/jo071115p
Xu, L.; Farthing, A. K.; Dropinski, J. F.; Meinke, P. T.; McCallum, C.; Leavitt, P. S.; Hickey, E. J.; Colwell, L.; Barrett, J.; Liu, K. Bioorg. Med. Chem. Lett. 2009, 19, 3531.
doi: 10.1016/j.bmcl.2009.04.144
Hrnciar, P.; Ueda, Y.; Huang, S.; Leet, J. E.; Bronson, J. J. J. Org. Chem. 2002, 67, 8789.
doi: 10.1021/jo020385z
Pucci, M. J.; Bronson, J. J.; Barrett, J. F.; DenBleyker, K. L.; Discotto, L. F.; Fung-Tomc, J. C.; Ueda, Y. Antimicrob. Agents Chemother. 2004, 48, 3697.
doi: 10.1128/AAC.48.10.3697-3701.2004
Regueiro-Ren, A.; Naidu, B. N.; Zheng, X.; Hudyma, T. W.; Connolly, T. P.; Matiskella, J. D.; Zhang, Y.; Kim, O. K.; Sorenson, M. E.; Pucci, M. J.; Clark, J.; Bronson, J. J.; Ueda, Y. Bioorg. Med. Chem. Lett. 2004, 14, 171.
doi: 10.1016/j.bmcl.2003.09.061
Naidu, B. N.; Sorenson, M. E.; Hudyma, T.; Zheng, X.; Zhang, Y.; Bronson, J. J.; Pucci, M. J.; Clark, J. M.; Ueda, Y. Bioorg. Med. Chem. Lett. 2004, 14, 3743.
doi: 10.1016/j.bmcl.2004.04.102
Golik, J.; Wong, H. S. L.; Chen, S. H.; Doyle, T. W.; Wright, J. J. K.; Knipe, J.; Rose, W. C.; Casazzam, A. M.; Vyas, D. M. Bioorg. Med. Chem. Lett. 1996, 6, 1837.
doi: 10.1016/0960-894X(96)00321-6
Tavecchia, P.; Gentili, P.; Kurz, M.; Sottani, C.; Bonfichi, R.; Selva, E.; Lociuro, S.; Restelli, E.; Ciabatti, R. Tetrahedron 1995, 51, 4867.
doi: 10.1016/0040-4020(95)00171-4
Tavecchia, P.; Kruz, M.; Colombo, L.; Bonfichi, R.; Selva, E.; Lociuro, S.; Marzorati, E.; Ciabatti, R. Tetrahedron 1996, 52, 8763.
doi: 10.1016/0040-4020(96)00417-6
Lociuro, S.; Tavecchia, P.; Marzorati, E.; Goldstein, B. P.; Denaro, M.; Ciabatti, R. J. Antibiot. 1997, 50, 344..
doi: 10.7164/antibiotics.50.344
LaMarche, M. J.; Leeds, J. A.; Amaral, K.; Brewer, J. T.; Bushell, S. M.; Dewhurst, J. M.; Dzink-Fox, J.; Gangl, E.; Goldovitz, J.; Jain, A.; Mullin, S.; Neckermann, G.; Osborne, C.; Palestrant, D.; Patane, M. A.; Rann, E. M.; Sachdeva, M.; Shao, J.; Tiamfook, S.; Whitehead, L.; Yu, D. J. Med. Chem. 2011, 54, 8099.
doi: 10.1021/jm200938f
LaMarche, M. J.; Leeds, J. A.; Dzink-Fox, J.; Mullin, S.; Patane, M. A.; Rann, E. M.; Tiamfook, S. Bioorg. Med. Chem. Lett. 2011, 21, 3210.
doi: 10.1016/j.bmcl.2011.04.048
LaMarche, M. J.; Leeds, J. A.; Amaral, A.; Brewer, J. T.; Bushell, S. M.; Deng, G.; Dewhurst, J. M.; Ding, J.; Dzink-Fox, J.; Gamber, G.; Jain, A.; Lee, K.; Lee, L.; Lister, T.; McKenney, D.; Mullin, S.; Osborne, C.; Palestrant, D.; Patane, M. A.; Rann, E. M.; Sachdeva, M.; Shao, J.; Tiamfook, S.; Trzasko, A.; Whitehead, L.; Yifru, A.; Yu, D.; Yan, W.; Zhu, Q. J. Med. Chem. 2012, 55, 2376.
doi: 10.1021/jm201685h
LaMarche, M. J.; Leeds, J. A.; Dzink-Fox, J.; Gunderson, K.; Krastel, P.; Memmert, K.; Patane, M. A.; Rann, E. M.; Schmitt, E.; Tiamfook, S.; Wang, B. J. Med. Chem. 2011, 54, 2517.
doi: 10.1021/jm101602q
Trzasko, A.; Leeds, J. A.; Praestgaard, J.; Lamarche, M. J.; McKenney, D. Antimicrob. Agents Chemother. 2012, 56, 4459.
doi: 10.1128/AAC.06355-11
Ting, L. S.; Praestgaard, J.; Grunenberg, N.; Yang, J. C.; Leeds, J. A.; Pertel, P. Antimicrob. Agents Chemother. 2012, 56, 5946.
doi: 10.1128/AAC.00867-12
Fabbretti, A.; He, C. G.; Gaspari, E.; Maffioli, S.; Brandi, L.; Spurio, R.; Sosio, M.; Jabes, D.; Donadio, S. Antimicrob. Agents Chemother. 2015, 59, 4560.
doi: 10.1128/AAC.05155-14
Schoof, S.; Baumann, S.; Ellinger, B.; Arndt, H. D. ChemBioChem 2009, 10, 242.
doi: 10.1002/cbic.v10:2
Baumann, S.; Schoof, S.; Bolten, M.; Haering, C.; Takagi, M.; Shin-ya, K.; Arndt, H. D. J. Am. Chem. Soc. 2010, 132, 6973.
doi: 10.1021/ja909317n
Myers, C. L.; Hang, P. C.; Ng, G.; Yuen, J.; Honek, J. F. Bioorg. Med. Chem. 2010, 18, 4231.
doi: 10.1016/j.bmc.2010.04.098
Jonker, H. R.; Baumann, S.; Wolf, A.; Schoof, S.; Hiller, F.; Schulte, K. W.; Kirschner, K. N.; Schwalbe, H.; Arndt, H. D. Angew. Chem., Int. Ed. Engl. 2011, 50, 3308.
doi: 10.1002/anie.201003582
Hegde, N. S.; Sanders, D. A.; Rodriguez, R.; Balasubramanian, S. Nat. Chem. 2011, 3, 725.
doi: 10.1038/nchem.1114
Luo, X.; Zambaldo, C.; Liu, T.; Zhang, Y.; Xuan, W.; Wang, C.; Reed, S. A.; Yang, P. Y.; Wang, R. E.; Javahishvili, T.; Schultz, P. G.; Young, T. S. Proc. Natl. Acad. Sci. U. S. A. 2016, 113, 3615.
doi: 10.1073/pnas.1602733113
Liao, R.; Liu, W. J. Am. Chem. Soc. 2011, 133, 2852.
doi: 10.1021/ja1111173
Bowers, A. A.; Acker, M. G.; Koglin, A.; Walsh, C. T. J. Am. Chem. Soc. 2010, 132, 7519.
doi: 10.1021/ja102339q
Bowers, A. A.; Acker, M. G.; Young, T. S.; Walsh, C. T. J. Am. Chem. Soc. 2012, 134, 10313.
doi: 10.1021/ja302820x
Young, T. S.; Dorrestein, P. C.; Walsh, C. T. Chem. Biol. 2012, 19, 1600.
doi: 10.1016/j.chembiol.2012.10.013
Guo, H.; Wang, J.; Li, Y.; Yu, Y.; Zheng, Q.; Wu, J.; Liu, W. Chem. Sci. 2014, 5, 240.
doi: 10.1039/C3SC52015C
Duan, P.; Zheng, Q.; Lin, Z.; Wang, S.; Chen, D.; Liu, W. Org. Chem. Front. 2016, 3, 1254.
doi: 10.1039/C6QO00320F
Zhang, F.; Kelly, W. L. ACS Chem. Biol. 2015, 10, 998.
doi: 10.1021/cb5007745
Zhang, F.; Li, C.; Kelly, W. L. ACS Chem. Biol. 2016, 11, 415.
doi: 10.1021/acschembio.5b00731
Zhang, Q.; Chen, D.; Lin, J.; Liao, R.; Tong, W.; Xu, Z.; Liu, W. J. Biol. Chem. 2011, 286, 21287.
doi: 10.1074/jbc.M111.224832
Duan, L.; Wang, S.; Liao, R.; Liu, W. Chem. Biol. 2012, 19, 443.
doi: 10.1016/j.chembiol.2012.02.008
Zhang, Q.; Li, Y.; Chen, D.; Yu, Y.; Duan, L.; Shen, B.; Liu, W. Nat. Chem. Biol. 2011, 7, 154.
doi: 10.1038/nchembio.512
Wang, S.; Zheng, Q.; Wang, J.; Zhao, Z.; Li, Q.; Yu, Y.; Wang, R.; Liu, W. Org. Chem. Front. 2015, 2, 106.
doi: 10.1039/C4QO00288A
Zheng, Q.; Wang, Q.; Wang, S.; Wu, J.; Gao, Q.; Liu, W. Chem. Biol. 2015, 22, 1002.
doi: 10.1016/j.chembiol.2015.06.019
Wang, S.; Zheng, Q.; Wang, J.; Chen, D.; Yu, Y.; Liu, W. Org. Chem. Front. 2016, 3, 496.
doi: 10.1039/C5QO00433K
Zheng, Q.; Wang, S.; Liao, R.; Liu, W. ACS Chem. Biol. 2016, 11, 2673.
doi: 10.1021/acschembio.6b00419
Zheng, Q.; Wang, S.; Duan, P.; Liao, R.; Chen, D.; Liu, W. Proc. Natl. Acad. Sci. U. S. A. 2016, 113, 14318.
doi: 10.1073/pnas.1612607113
Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
Chao Liu , Huan Yu , Jiaming Li , Xi Yu , Zhuangzhi Yu , Yuxi Song , Feng Zhang , Qinfang Zhang , Zhigang Zou . Facile synthesis of hierarchical Ti3C2/Bi12O17Br2 Schottky heterojunction with photothermal effect for solar-driven antibiotics photodegradation. Acta Physico-Chimica Sinica, 2025, 41(7): 100075-. doi: 10.1016/j.actphy.2025.100075
Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
Bingliang Li , Yuying Han , Dianyang Li , Dandan Liu , Wenbin Shang . One-Step Synthesis of Benorilate Guided by Green Chemistry Principles and in vivo Dynamic Evaluation. University Chemistry, 2024, 39(6): 342-349. doi: 10.3866/PKU.DXHX202311070
Ying Zhang , Fang Ge , Zhimin Luo . AI-Driven Biochemical Teaching Research: Predicting the Functional Effects of Gene Mutations. University Chemistry, 2025, 40(3): 277-284. doi: 10.12461/PKU.DXHX202412104
Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
Hongyan Chen , Yajun Hou , Shui Hu , Zhuoxun Wei , Fang Zhu , Chengyong Su . Construction of Synthetic Chemistry Experiment of the Chemistry “101 Plan”. University Chemistry, 2024, 39(10): 58-63. doi: 10.12461/PKU.DXHX202409109
Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
Cunming Yu , Dongliang Tian , Jing Chen , Qinglin Yang , Kesong Liu , Lei Jiang . Chemistry “101 Program” Synthetic Chemistry Experiment Course Construction: Synthesis and Properties of Bioinspired Superhydrophobic Functional Materials. University Chemistry, 2024, 39(10): 101-106. doi: 10.12461/PKU.DXHX202408008
Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
Renxiu Zhang , Xin Zhao , Yunfei Zhang . Application of Electrochemical Synthesis in the Teaching of Organic Chemistry. University Chemistry, 2025, 40(4): 174-180. doi: 10.12461/PKU.DXHX202406116
Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
Li Jiang , Changzheng Chen , Yang Su , Hao Song , Yanmao Dong , Yan Yuan , Li Li . Electrochemical Synthesis of Polyaniline and Its Anticorrosive Application: Improvement and Innovative Design of the “Chemical Synthesis of Polyaniline” Experiment. University Chemistry, 2024, 39(3): 336-344. doi: 10.3866/PKU.DXHX202309002
Xiangyu CAO , Jiaying ZHANG , Yun FENG , Linkun SHEN , Xiuling ZHANG , Juanzhi YAN . Synthesis and electrochemical properties of bimetallic-doped porous carbon cathode material. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 509-520. doi: 10.11862/CJIC.20240270
Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C3N4纳米片用于高效光催化产H2O2. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
Benhua Wang , Chaoyi Yao , Yiming Li , Qing Liu , Minhuan Lan , Guipeng Yu , Yiming Luo , Xiangzhi Song . 一种基于香豆素氟离子荧光探针的合成、表征及性能测试——“科研反哺教学”在有机化学综合实验教学中的探索与实践. University Chemistry, 2025, 40(6): 201-209. doi: 10.12461/PKU.DXHX202408070
Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011