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Indole methylation protects diketopiperazine configuration in the maremycin biosynthetic pathway

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Abstract

The maremycin biosynthetic gene cluster has been identified in Streptomyces sp. B9173. Comparative metabolic profiling with knockout mutant strains led to the identification of new products correlated to the maremycin biosynthesis, in particular the “demethyl”-maremycins with an unexpected D-tryptophan unit. A biosynthetic pathway for the maremycins is proposed and plausible reasoning for tryptophan epimerization in the demethylmaremycin biosynthesis is also provided.

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References

  1. Schultz AW, Oh DC, Carney JR, Williamson RT, Udwary DW, Jensen PR, Gould SJ, Fenical W, Moore BS. J Am Chem Soc, 2008, 130: 4507–4516

    Article  CAS  Google Scholar 

  2. Dolan SK, O’keeffe G, Jones GW, Doyle S. Trends Microbiol, 2015, 23: 419–428

    Article  CAS  Google Scholar 

  3. Daugan A, Grondin P, Ruault C, Le Monnier de Gouville AC, Coste H, Kirilovsky J, Hyafil F, Labaudinière R. J Med Chem, 2003, 46: 4525–4532

    Article  CAS  Google Scholar 

  4. Liddle J, Allen MJ, Borthwick AD, Brooks DP, Davies DE, Edwards RM, Exall AM, Hamlett C, Irving WR, Mason AM, Mccafferty GP, Nerozzi F, Peace S, Philp J, Pollard D, Pullen MA, Shabbir SS, Sollis SL, Westfall TD, Woollard PM, Wu C, Hickey DMB. Bioorg Med Chem Lett, 2008, 18: 90–94

    Article  CAS  Google Scholar 

  5. Balk-Bindseil W, Helmke E, Weyland H, Laatsch H. Liebigs Ann, 1995, 1995: 1291–1294

    Article  Google Scholar 

  6. Tang YQ, Sattler I, Thiericke R, Grabley S, Feng XZ. Eur J Org Chem, 2001, 2001: 261–267

    Article  Google Scholar 

  7. Ueda T, Inada M, Okamoto I, Morita N, Tamura O. Org Lett, 2008, 10: 2043–2046

    Article  CAS  Google Scholar 

  8. Liu Y, Zhang L, Jia Y. Tetrahedron Lett, 2012, 53: 684–687

    Article  CAS  Google Scholar 

  9. Zou Y, Fang Q, Yin H, Liang Z, Kong D, Bai L, Deng Z, Lin S. Angew Chem Int Ed, 2013, 52: 12951–12955

    Article  CAS  Google Scholar 

  10. Rangaswamy V, Jiralerspong S, Parry R, Bender CL. Proc Natl Acad Sci, 1998, 95: 15469–15474

    Article  CAS  Google Scholar 

  11. Rottig M, Medema MH, Blin K, Weber T, Rausch C, Kohlbacher O. Nucleic Acids Res, 2011, 39: W362–W367

    Article  Google Scholar 

  12. Stachelhaus T, Mootz HD, Marahiel MA. Chem Biol, 1999, 6: 493–505

    Article  CAS  Google Scholar 

  13. Davies DB, Khaled MA. J Chem Soc Perkin Trans II, 1976: 1238–1244

    Google Scholar 

  14. Scharf DH, Habel A, Heinekamp T, Brakhage AA, Hertweck C. J Am Chem Soc, 2014, 136: 11674–11679

    Article  CAS  Google Scholar 

  15. Lv M, Zhao J, Deng Z, Yu Y. Chem Biol, 2015, 22: 1313–1324

    Article  CAS  Google Scholar 

  16. Hayaishi J, Nishizuka Y, Hayaishi O. J Biol Chem, 1963, 238: 1441–1446

    Google Scholar 

  17. Siodlak D. Amino Acids, 2015, 47: 1–17

    Article  CAS  Google Scholar 

  18. Butler CS, Mason JR. Adv Microb Physiol, 1996, 38: 47–84

    Article  Google Scholar 

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Authors and Affiliations

  1. State Key Laboratory of Microbial Metabolism; Joint International Laboratory on Metabolic & Developmental Sciences; School of Life Sciences & Biotechnology, Shanghai Jiao Tong University, Shanghai, 200030, China

    Yingxia Lan, Yi Zou, Tingting Huang, Xiaozheng Wang, Nelson L. Brock, Zixin Deng & Shuangjun Lin

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  1. Yingxia Lan
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  2. Yi Zou
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  3. Tingting Huang
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  4. Xiaozheng Wang
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  5. Nelson L. Brock
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  6. Zixin Deng
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  7. Shuangjun Lin
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Corresponding authors

Correspondence to Nelson L. Brock or Shuangjun Lin.

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Lan, Y., Zou, Y., Huang, T. et al. Indole methylation protects diketopiperazine configuration in the maremycin biosynthetic pathway. Sci. China Chem. 59, 1224–1228 (2016). https://doi.org/10.1007/s11426-016-0026-7

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  • DOI: https://doi.org/10.1007/s11426-016-0026-7

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