SIOC English
有机化学
高级检索

有机化学 >

2020 , Vol. 40 >Issue 10: 3120 - 3131

DOI: https://doi.org/10.6023/cjoc202005071

综述与进展

基于生物合成的双环硫肽类抗生素结构改造进展

  • 张鄂 ,
  • 陈单丹 ,
  • 王守锋 ,
  • 刘文
展开
  • a 济南大学化学化工学院 山东省氟化学化工材料重点实验室 济南 250022;
    b 中国科学院上海有机化学研究所 生命有机化学国家重点实验室 上海 200032;
    c 中国科学院上海有机化学研究所 湖州生物制造中心 浙江湖州 313000

收稿日期: 2020-05-26

  修回日期: 2020-06-20

  网络出版日期: 2020-07-09

基金资助

国家自然科学基金（Nos.31972850，21750004，21520102004）、山东省重点研发计划（No.2019GSF108223）、中国科学院（Nos.QYZDJ-SSW-SLH037，XDB20020200）、上海市科委（No.17JC1405100）、中国科学院青年创新促进会（No.2017303）和王宽诚教育基金会资助项目.

收起

Progress in Structural Modification of Bicyclic Thiopeptide Antibiotics Based on Biosynthesis

  • Zhang E ,
  • Chen Dandan ,
  • Wang Shoufeng ,
  • Liu Wen
Expand
  • a Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022;
    b State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
    c Huzhou Center of Bio-Synthetic Innovation, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Huzhou, Zhejiang 313000

Received date: 2020-05-26

  Revised date: 2020-06-20

  Online published: 2020-07-09

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 31972850, 21750004, 21520102004), the Shandong Key Research Program (No. 2019GSF108223), the Chinese Academy of Sciences (Nos. QYZDJ-SSW-SLH037, XDB20020200), the Science and Technology Commission of Shanghai Municipality (No. 17JC1405100), the Youth Innovation Promotion Association of the Chinese Academy of Sciences (No. 2017303), and the K. C. Wong Education Foundation.

Fold

摘要

硫肽类抗生素是一类由微生物次级代谢产生的富含硫元素且结构被高度修饰的聚噻（噁）唑多肽类天然产物，具有良好的生物活性.由于水溶性差以及生物利用度低等问题，导致该类抗生素在临床上的应用受到限制.在了解其生物合成机制的基础上，通过合理的生物工程改造来获得硫肽类似物的方法成了生物学家们关注的焦点.以双环硫肽家族中的硫链丝菌素和那西肽为代表，综述了双环硫肽类抗生素结构改造的进展.

关键词： 生物合成; 硫链丝菌素; 那西肽; 结构改造

本文引用格式

张鄂 , 陈单丹 , 王守锋 , 刘文 . 基于生物合成的双环硫肽类抗生素结构改造进展[J]. 有机化学, 2020 , 40(10) : 3120 -3131 . DOI: 10.6023/cjoc202005071

Abstract

Thiopeptide antibiotics are a class of natural products with polythiophene (oxazol) polypeptides, which are rich in sulfur and highly modified. They are produced by secondary metabolism of microorganisms and have good biological activities. Developing thiopeptides into clinic is currently a challenge partly due to their low aqueous solubility and associated poor bioavailability. On the basis of understanding the mechanism of their biosynthesis, the method of obtaining thiopeptide analogues via reasonable bioengineering has become the research focus of biologists. In this paper, the advances in structural modifications of bicyclic thiopeptides by taking thiostrepton and nosiheptide as representatives are reviewed.

Key words： biosynthesis; thiostrepton; nosiheptide; structural modifications

参考文献

[1] Arnison, P. G.; Bibb, M. J.; Bierbaum, G.; Bowers, A. A.; Bugni, T. S.; Bulaj, G.; Camarero, J. A.; Campopiano, D. J.; Challis, G. L.; Clardy, J.; Cotter, P. D.; Craik, D. J.; Dawson, M.; Dittmann, E.; Donadio, S.; Dorrestein, P. C.; Entian, K. D.; Fischbach, M. A.; Garavelli, J. S.; Goransson, U.; Gruber, C. W.; Haft, D. H.; Hemscheidt, T. K.; Hertweck, C.; Hill, C.; Horswill, A. R.; Jaspars, M.; Kelly, W. L.; Klinman, J. P.; Kuipers, O. P.; Link, A. J.; Liu, W.; Marahiel, M. A.; Mitchell, D. A.; Moll, G. N.; Moore, B. S.; Muller, R.; Nair, S. K.; Nes, I. F.; Norris, G. E.; Olivera, B. M.; Onaka, H.; Patchett, M. L.; Piel, J.; Reaney, M. J.; Rebuffat, S.; Ross, R. P.; Sahl, H. G.; Schmidt, E. W.; Selsted, M. E.; Severinov, K.; Shen, B.; Sivonen, K.; Smith, L.; Stein, T.; Sussmuth, R. D.; Tagg, J. R.; Tang, G. L.; Truman, A. W.; Vederas, J. C.; Walsh, C. T.; Walton, J. D.; Wenzel, S. C.; Willey, J. M.; van der Donk, W. A. Nat. Prod. Rep. 2013, 30, 108.
[2] Walsh, C. T. Science 2004, 303, 1805.
[3] Yang, X.; van der Donk, W. A. Chem. Eur. J. 2013, 19, 7662.
[4] Bagley, M. C.; Dale, J. W.; Merritt, E. A.; Xiong, X. Chem. Rev. 2005, 105, 685.
[5] Ortega, M. A.; van der Donk, W. A. Cell Chem. Biol. 2016, 23, 31.
[6] Tl, S. U. Br. J. Exp. Pathol. 1948, 29, 473.
[7] Li, C.; Kelly, W. L. Nat. Prod. Rep. 2010, 27, 153.
[8] Hensens, O. D.; Albers-Schönberg, G. Tetrahedron Lett. 1978, 19, 3649.
[9] Li, J.; Qu, X.; He, X.; Duan, L.; Wu, G.; Bi, D.; Deng, Z.; Liu, W.; Ou, H. PLoS One 2012, 7, e45878.
[10] Vandeputte, J.; Dutcher, J. D. Antibiot. Annu. 1955~1956, 560.
[11] Trejo, W. H.; Dean, L. D.; Pluscec, J.; Meyers, E.; Brown, W. E. J. J. Antibiot (Tokyo) 1977, 30, 639.
[12] (a) Anderson, B.; Hodgkin, D. C.; Viswamitra, M. A. Nature 1970, 225, 233.
(b) Hensens, O. D.; Albers-Schönberg, G. J. Antibiot (Tokyo) 1983, 36, 814.
(c) Hensens, O. D.; Albers-Schönberg, G. J. Antibiot (Tokyo) 1983, 36, 832.
(d) Hensens, O. D.; Albers-Schonberg, G.; Anderson, B. F. J. Antibiot (Tokyo) 1983, 36, 799.
[13] Benazet, F.; Cartier, M.; Florent, J.; Godard, C.; Ninet, L. Experientia 1980, 36, 414.
[14] Depaire, H.; Thomas, J. P.; Brun, A.; Olesker, A.; Lukacs, G. Tetrahedron Lett. 1977, 18, 1397.
[15] Bhat, U. G.; Halasi, M.; Gartel, A. L. PLoS One 2009, 4, e6593.
[16] Rogers, M. J.; Cundliffe, E.; Mccutchan, T. F. Antimicrob. Agents Chemother. 1998, 42, 715.
[17] (a) 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. Bioorg. Med. Chem. Lett. 2004, 14, 5573.
(b) Zhang, C.; Herath, K.; Jayasuriya, H.; Ondeyka, J. G.; Zink, D. L.; Occi, J.; Birdsall, G.; Venugopal, J.; Ushio, M.; Burgess, B. J. Nat. Prod. 2009, 72, 841.
(c) Zhang, C.; Occi, J.; Masurekar, P.; Barrett, J. F.; Zink, D. L.; Smith, S.; Onishi, R.; Ha, S.; Salazar, O.; Genilloud, O. J. Am. Chem. Soc. 2008, 130, 12102.
[18] (a) Xing, Y.; Draper, D. E. Biochemistry 1996, 35, 1581.
(b) Blyn, L. B.; Risen, L. M.; Griffey, R. H.; Draper, D. E. Nucleic Acids Res. 2000, 28, 1778.
(c) Wimberly, B. T.; Guymon, R.; McCutcheon, J. P.; White, S. W.; Ramakrishnan, V. Cell 1999, 97, 491.
(d) Lentzen, G.; Klinck, R.; Matassova, N.; Aboul-ela, F.; Murchie, A. I. Chem. Biol. 2003, 10, 769.
(e) Harms, J. M.; Wilson, D. N.; Schluenzen, F.; Connell, S. R.; Fucini, P. Mol. Cell 2008, 30, 26.
(f) Bo, T. P.; Leviev, I.; Mankin, A. S.; Garrett, R. A. J. Mol. Biol. 1998, 276, 391.
(g) Gonzalez, R. L.; Chu, S.; Puglisi, J. D. RNA (New York, N. Y.) 2007, 13, 2091.
[19] Zheng, Q.; Wang, Q.; Wang, S.; Wu, J.; Gao, Q.; Liu, W. Chem. Biol. 2015, 22, 1002.
[20] Houck, D. R.; Chen, L. C.; Keller, P. J.; Beale, J. M.; Floss, H. G. J. Am. Chem. Soc. 1988, 110, 5800.
[21] Houck, D. R.; Chen, L. C.; Keller, P. J.; Beale, J. M.; Floss, H. G. J. Am. Chem. Soc. 1993, 115, 7992.
[22] Yu, Y.; Duan, L.; Zhang, Q.; Liao, R.; Ding, Y.; Pan, H.; Evelyn, W. P.; Tang, G. L.; Shen, B.; Liu, W. ACS Chem. Biol. 2009, 4, 855.
[23] (a) Liao, R.; Duan, L.; Lei, C.; Pan, H.; Ding, Y.; Zhang, Q.; Chen, D.; Shen, B.; Yu, Y.; Liu, W. Chem. Biol. 2009, 16, 141.
(b) Kelly, W. L.; Pan, L.; Li, C. J. Am. Chem. Soc. 2009, 131, 4327.
[24] Morris, R. P.; Leeds, J. A.; Naegeli, H. U.; Oberer, L.; Memmert, K.; Weber, E.; LaMarche, M. J.; Parker, C. N.; Burrer, N.; Esterow, S.; Hein, A. E.; Schmitt, E. K.; Krastel, P. J. Am. Chem. Soc. 2009, 131, 5946.
[25] Hudson, G. A.; Zhang, Z.; Tietz, J. I.; Mitchell, D. A.; van der Donk, W. A. J. Am. Chem. Soc. 2015, 137, 16012.
[26] Zhang, Q.; Li, Y. X.; Chen, D. D.; Yu, Y.; Duan, L.; Shen, B.; Liu, W. Nat. Chem. Biol. 2011, 7, 154.
[27] Sicoli, G.; Mouesca, J. M.; Zeppieri, L.; Amara, P.; Martin, L.; Barra, A. L.; Fontecilla Camps, J. C.; Gambarelli, S.; Nicolet, Y. Science 2016, 351, 1320.
[28] Qiu, Y. P.; Du, Y. N.; Zhang, F.; Liao, R. J.; Zhou, S. X.; Peng, C.; Guo, Y. L.; Liu, W. J. Am. Chem. Soc. 2017, 139, 18186.
[29] Qiu, Y. P.; Du, Y. N.; Wang, S. F.; Zhou, S. X.; Guo, Y. L.; Liu, W. Org. Lett. 2019, 21, 1502.
[30] Wang, B.; LaMattina, J. W.; Marshall, S. L.; Booker, S. J. J. Am. Chem. Soc. 2019, 141, 5788.
[31] Duan, L.; Wang, S.; Liao, R.; Liu, W. Chem. Biol. 2012, 19, 443.
[32] Liu, W. Y.; Ma, M.; Xue, Y. J.; Liu, N.; Wang, S. Z.; Chen, Y. J. ChemBioChem 2013, 14, 573.
[33] Wang, S. Z.; Zheng, X. L.; Pan, Q.; Chen, Y. J. RSC Adv. 2016, 6, 94643.
[34] Kwok, M. M.; Myatt, S. S.; Marson, C. M.; Coombes, R. C.; Constantinidou, D.; Lam, W. F. Mol. Cancer Ther. 2008, 7, 2022.
[35] Li, C.; Zhang, F.; Kelly, W. L. Chem. Commun. 2012, 48, 558.
[36] Zhang, F.; Li, C.; Kelly, W. L. ACS Chem. Biol. 2015, 11, 415.
[37] Zhang, F.; Kelly, W. L. ACS Chem. Biol. 2015, 10, 998.
[38] Guo, H.; Wang, J.; Li, Y. M.; Yu, Y.; Zheng, Q. F.; Wu, J. Q.; Liu, W. Chem. Sci. 2014, 5, 240.
[39] Duan, P. P.; Zheng, Q. F.; Lin, Z.; Wang, S. F.; Chen, D. D.; Liu, W. Org. Chem. Front. 2016, 3, 1254.
[40] Liu, W. Y.; Xue, Y. J.; Ma, M.; Wang, S. Z.; Liu, N.; Chen, Y. J. ChemBioChem 2013, 14, 1544.
[41] Bai, X. B.; Guo, H.; Chen, D. D.; Yang, Q.; Tao, J.; Liu, W. Org. Chem. Front. 2020, 7, 584.
[42] Liao, R. J.; Liu, W. J. Am. Chem. Soc. 2011, 133, 2852.
[43] Liu, J.; Lin, Z.; Li, Y.; Zheng, Q.; Chen, D.; Liu, W. Org. Biomol. Chem. 2019, 17, 3727.
[44] (a) Liu, J.; Lin, Z.; Chen, H.; Guo, H.; Tao, J.; Liu, W. Chin. J. Chem. 2019, 37, 35.
(b) Zheng, Q. F.; Wang, S. F.; Liao, R. J.; Liu, W. ACS Chem. Biol. 2016, 11, 2673.
[45] Wang, S. F.; Zheng, Q. F.; Wang, J. F.; Zhao, Z. X.; Li, Q. Y.; Yu, Y. S.; Wang, R. X.; Liu, W. Org. Chem. Front. 2015, 2, 106.
[46] Wang, J.; Lin, Z.; Bai, X. B.; Tao, J.; Liu, W. Org. Chem. Front. 2019, 6, 1194.
[47] Wang, S. F.; Zheng, Q. F.; Wang, J. F.; Chen, D. D.; Yu, Y. S.; Wen, L. Org. Chem. Front. 2016, 3, 496.
[48] Zhang, E.; Guo, H.; Chen, D.; Yang, Q.; Fan, Y.; Yin, Y.; Wang, W.; Chen, D.; Wang, S.; Liu, W. Org. Biomol. Chem. 2020, 18, 4051.
Options
文章导航

/

〈 〉