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 shu

Progress in Synthesis of Thiopeptide Antibiotics Analogues

  • Corresponding author: Wang Shoufeng, chm_wangsf@ujn.edu.cn Liu wen, wliu@sioc.ac.cn
  • Received Date: 15 February 2017
    Revised Date: 20 March 2017
    Available Online: 10 July 2017

    Fund Project: the Natural Science Foundation of Shandong Province ZR2016HM44the National Natural Science Foundation of China 31430005Project supported by the National Natural Science Foundation of China (No. 31430005) and the Natural Science Foundation of Shandong Province (No.ZR2016HM44)

Figures(13)

  • Thiopeptide antibiotics, which are a growing class of sulfur-rich and highly modified polyazolyl peptide natural products, have been appreciated because of their complex structures, potent biological activities and unusual modes of action. Recently, a great deal of effort has been devoted to the development of various approaches for the efficient synthesis of thiopeptide antibiotics analogues. This review summarizes synthetic approaches towards thiopeptide antibiotics analogues via semisynthesis, combinatorial biosynthesis and precursor-directed mutasynthesis.
  • 加载中
    1. [1]

      Bagley, M. C.; Dale, J. W.; Merritt, E. A.; Xiong, X. Chem. Rev. 2005, 105, 685.  doi: 10.1021/cr0300441

    2. [2]

      Li, C.; Kelly, W. L. Nat. Prod. Rep. 2010, 27, 153.  doi: 10.1039/B922434C

    3. [3]

      Hensens, O. D.; Albers-Schönberg, G. Tetrahedron Lett. 1978, 19, 3649.

    4. [4]

      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

    5. [5]

      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

    6. [6]

      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

    7. [7]

      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

    8. [8]

      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

    9. [9]

      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

    10. [10]

      Regueiro-Ren, A.; Ueda, Y. J. Org. Chem. 2002, 67, 8699.  doi: 10.1021/jo0261698

    11. [11]

      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

    12. [12]

      Xu, L.; Farthing, A. K.; Shi, Y.; Meinke, P. T.; Liu, K. J. Org. Chem. 2007, 72, 7447.  doi: 10.1021/jo071115p

    13. [13]

      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

    14. [14]

      Hrnciar, P.; Ueda, Y.; Huang, S.; Leet, J. E.; Bronson, J. J. J. Org. Chem. 2002, 67, 8789.  doi: 10.1021/jo020385z

    15. [15]

      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

    16. [16]

      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

    17. [17]

      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

    18. [18]

      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

    19. [19]

      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

    20. [20]

      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

    21. [21]

      Lociuro, S.; Tavecchia, P.; Marzorati, E.; Goldstein, B. P.; Denaro, M.; Ciabatti, R. J. Antibiot. 1997, 50, 344..  doi: 10.7164/antibiotics.50.344

    22. [22]

      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

    23. [23]

      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

    24. [24]

      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

    25. [25]

      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

    26. [26]

      Trzasko, A.; Leeds, J. A.; Praestgaard, J.; Lamarche, M. J.; McKenney, D. Antimicrob. Agents Chemother. 2012, 56, 4459.  doi: 10.1128/AAC.06355-11

    27. [27]

      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

    28. [28]

      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

    29. [29]

      Schoof, S.; Baumann, S.; Ellinger, B.; Arndt, H. D. ChemBioChem 2009, 10, 242.  doi: 10.1002/cbic.v10:2

    30. [30]

      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

    31. [31]

      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

    32. [32]

      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

    33. [33]

      Hegde, N. S.; Sanders, D. A.; Rodriguez, R.; Balasubramanian, S. Nat. Chem. 2011, 3, 725.  doi: 10.1038/nchem.1114

    34. [34]

      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

    35. [35]

      Liao, R.; Liu, W. J. Am. Chem. Soc. 2011, 133, 2852.  doi: 10.1021/ja1111173

    36. [36]

      Bowers, A. A.; Acker, M. G.; Koglin, A.; Walsh, C. T. J. Am. Chem. Soc. 2010, 132, 7519.  doi: 10.1021/ja102339q

    37. [37]

      Bowers, A. A.; Acker, M. G.; Young, T. S.; Walsh, C. T. J. Am. Chem. Soc. 2012, 134, 10313.  doi: 10.1021/ja302820x

    38. [38]

      Young, T. S.; Dorrestein, P. C.; Walsh, C. T. Chem. Biol. 2012, 19, 1600.  doi: 10.1016/j.chembiol.2012.10.013

    39. [39]

      Guo, H.; Wang, J.; Li, Y.; Yu, Y.; Zheng, Q.; Wu, J.; Liu, W. Chem. Sci. 2014, 5, 240.  doi: 10.1039/C3SC52015C

    40. [40]

      Duan, P.; Zheng, Q.; Lin, Z.; Wang, S.; Chen, D.; Liu, W. Org. Chem. Front. 2016, 3, 1254.  doi: 10.1039/C6QO00320F

    41. [41]

      Zhang, F.; Kelly, W. L. ACS Chem. Biol. 2015, 10, 998.  doi: 10.1021/cb5007745

    42. [42]

      Zhang, F.; Li, C.; Kelly, W. L. ACS Chem. Biol. 2016, 11, 415.  doi: 10.1021/acschembio.5b00731

    43. [43]

      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

    44. [44]

      Duan, L.; Wang, S.; Liao, R.; Liu, W. Chem. Biol. 2012, 19, 443.  doi: 10.1016/j.chembiol.2012.02.008

    45. [45]

      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

    46. [46]

      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

    47. [47]

      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

    48. [48]

      Wang, S.; Zheng, Q.; Wang, J.; Chen, D.; Yu, Y.; Liu, W. Org. Chem. Front. 2016, 3, 496.  doi: 10.1039/C5QO00433K

    49. [49]

      Zheng, Q.; Wang, S.; Liao, R.; Liu, W. ACS Chem. Biol. 2016, 11, 2673.  doi: 10.1021/acschembio.6b00419

    50. [50]

      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

  • 加载中
    1. [1]

      Hui Shao ,  Huan Jiao ,  Qi Zhang ,  Yuming Zhao ,  Mingyu Yang . 融入课程思政的“截短侧耳素类抗生素泰妙菌素的合成及表征”化学创新实验教学设计. University Chemistry, 2026, 41(10): 379-389. doi: 10.12461/PKU.DXHX202511036

    2. [2]

      Weizhe Liu ,  Minghui Shi ,  Ruiqi Zhu ,  Bin Pan ,  Guofu Huang . 抗癌药物艾乐替尼的生物电子等排体的合成. University Chemistry, 2026, 41(5): 210-221. doi: 10.12461/PKU.DXHX202510066

    3. [3]

      Chengyan XU , Jiangnan YU , Yu LI , Xizhen PAN , Yinlin HOU , Wenmin WANG . Synthesis, structure, and bioactivity of a Ho4 complex bridged by azide group. Chinese Journal of Inorganic Chemistry, 2026, 42(7): 1453-1462. doi: 10.11862/CJIC.20260033

    4. [4]

      Longfei MA , Fang SI , Congjie PAN , Xinhua WANG . Synthesis and crystal structure of extended tetrathiafulvalene derivatives and cupric bromide charge transfer complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(6): 1229-1236. doi: 10.11862/CJIC.20250355

    5. [5]

      Chunyan Hu ,  Wei Wang ,  Zewei Mao ,  Mei Zhang ,  Lei Zhang ,  Yuping Lin . Three-stage progressive teaching reform and practice in organic chemistry experiments for pharmacy undergraduates: synthesis of coumarin-chalcone derivatives. University Chemistry, 2026, 41(7): 282-289. doi: 10.12461/PKU.DXHX202505011

    6. [6]

      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

    7. [7]

      Lixing ZHANG , Yaowen WANG , Xu HAN , Junhong ZHOU , Jinghui WANG , Liping LI , Guangshe LI . Research progress in the synthesis of fluorine-containing perovskites and their derivatives. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1689-1701. doi: 10.11862/CJIC.20250007

    8. [8]

      Qingyu Yang ,  Yuanhai Yu ,  Yanliu Wu ,  Ting Yang ,  Le Zhong ,  Wenhong Ruan ,  Jie Li . Digital Intelligence-Empowered Exploration of Copolymerized Polyacrylonitrile Synthesis and Application Experiments for Carbon Fiber Precursors. University Chemistry, 2026, 41(1): 41-56. doi: 10.12461/PKU.DXHX202506010

    9. [9]

      Chao Liu , Huan Yu , Jiaming Li , Xi Yu , Zhuangzhi Yu , Yuxi Song , Feng Zhang , Qinfang Zhang , Zhigang Zou . 具有光热效应的多级Ti3C2/Bi12O17Br2肖特基异质结简单合成及其太阳能驱动抗生素光降解的研究. Acta Physico-Chimica Sinica, 2025, 41(7): 100075-0. doi: 10.1016/j.actphy.2025.100075

    10. [10]

      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

    11. [11]

      Xiaomei Ai ,  Muran Lin ,  Jinlan Zeng ,  Jiwei Ren . 可见光催化绿色合成二肽化合物. University Chemistry, 2026, 41(5): 358-367. doi: 10.12461/PKU.DXHX202510007

    12. [12]

      Cun WANG , Shaohan XU , Yuqian ZHANG , Yaoyao ZHANG , Tao GONG , Rong WEN , Yuhang LIAO , Yanrong REN . Terbium complex electrochemiluminescent emitters: Synthesis and application in the detection of epinephrine. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1351-1360. doi: 10.11862/CJIC.20240427

    13. [13]

      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

    14. [14]

      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

    15. [15]

      Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428

    16. [16]

      Mengyang LI , Zhonghao NIU , Hao XU , Jingli XIE . One-pot synthesis of 4H-pyran derivatives catalyzed by viologen-modified metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2026, 42(7): 1513-1522. doi: 10.11862/CJIC.20250205

    17. [17]

      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

    18. [18]

      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

    19. [19]

      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

    20. [20]

      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

Metrics
  • PDF Downloads(27)
  • Abstract views(4506)
  • HTML views(753)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return