Download PDF
Synlett 2022; 33(01): 27-33
DOI: 10.1055/a-1662-7783
account

Long Journey on Daptomycin

Xuechen Li
I would like to express my gratitude to the funding agency for their generous supports over the years, including the Research Grants Council, University Grants Committee of Hong Kong (Grant Numbers C7038-15G, C5036-16G, and AoE/P-705/16), the Cubist Pharmaceutical Inc., the Peacock Program – Project Development Fund of Shenzhen, the National Basic Research Program of China, and the University of Hong Kong.
› Further Information
    Permissions and Reprints All articles of this category


Abstract

Over the past more than ten years, my laboratory has been engaged in the total synthesis, medicinal chemistry, and chemical biology studies on daptomycin. Our efforts are expected to advance new understanding of this effective cyclic lipodepsipeptide antibiotic. In this Account, this long journey is presented.

1 Introduction

2 Total Synthesis of Daptomycin

3 Medicinal Chemistry of Daptomycin

4 Molecular Comparison of Daptomycin and Kynomycin

5 New Insight into How Daptomycin Exerts Bactericidal Effect

6 Conclusion

Key words

daptomycin - total synthesis - ligation - medicinal chemistry - antibiotics


Publication History

Received: 03 September 2021

Accepted after revision: 06 October 2021

Accepted Manuscript online:
06 October 2021

Article published online:
26 October 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Raja A, LaBonte J, Lebbos J, Kirkpatrick P. Nat. Rev. Drug Discov. 2003; 2: 943
    CrossrefPubMed
  • 2 Taylor SD, Palmer M. Bioorg. Med. Chem. 2016; 24: 6253
    CrossrefPubMed
  • 3 Debono M, Barnhart M, Carrell CB, Hoffmann JA, Occolowitz JL, Abbott BJ, Fukuda DS, Hamill RL, Biemann K, Herlihy WC. J. Antibiot. 1987; 40: 761
    CrossrefPubMed

      • There were two patents filed on the total synthesis of daptomycin, see:
    • 4a Hill J, Parr I, Morytko M, Siedlecki J, Yu XY, Silverman K, Keith D, Finn J, Christensen D, Lazarova T, Watson A, Zhang Y. US6911525 2005
    • 4b Xu H, Lu T. CN101235080B 2010
    • 5a Malik A, Gade G, Lange AB. Peptides 2012; 34: 51
      CrossrefPubMed
    • 5b Ellis-Steinborner ST, Scanlon D, Musgrave IF, Tran TT, Hack S, Wang T, Abell AD, Tyler MJ, Bowie JH. Rapid Commun. Mass Spectrom. 2011; 25: 1735
      CrossrefPubMed
    • 5c Chuang PH, Hsieh PW, Yang YL, Hua KF, Chang FR, Shiea J, Wu SH, Wu YC. J. Nat. Prod. 2008; 71: 1365
      CrossrefPubMed
  • 6 Chen Y, Guillemin GJ. Int. J. Tryptophan Res. 2009; 2: 1
    CrossrefPubMed
  • 7 Ross FC, Botting NP, Leeson PD. Bioorg. Med. Chem. Lett. 1996; 6: 875
    CrossrefPubMed
  • 8 Lam HY, Zhang Y, Liu H, Xu J, Wong CT. T, Xu C, Li X. J. Am. Chem. Soc. 2013; 135: 6272
    CrossrefPubMed
  • 9 Wong CT. T, Lam HY, Li X. Org. Biomol. Chem. 2013; 11: 7616
    CrossrefPubMed
  • 10 Li X, Lam HY, Zhang Y, Chan CK. Org. Lett. 2010; 12: 1724
    CrossrefPubMed
  • 11 Zhang Y, Xu C, Lam HY, Lee CL, Li X. Proc. Natl. Acad. Sci. U.S.A. 2013; 110: 6657
    CrossrefPubMed
    • 12a Lohani CR, Taylor R, Palmer M, Taylor SD. Org. Lett. 17: 748
    • 12b Xu B, Hermant Y, Yang S.-H, Harris PW. R, Brimble MA. Chem. Eur. J. 2019; 25: 14101
      CrossrefPubMed
    • 12c Moreira R, Wolfe J, Taylor SD. Org. Biomol. Chem. 2021; 19: 3144
      CrossrefPubMed
  • 13 Wong CT. T, Lam HY, Song T, Chen G, Li X. Angew. Chem. Int. Ed. 2013; 52: 10212
    CrossrefPubMed
  • 14 Jin K, Sam IH, Po KH. L, Lin D, Zadeh EH. G, Chen S, Yuan Y, Li X. Nat. Commun. 2016; 7: 12394
    CrossrefPubMed
  • 15 Sun Z, Shang Z, Forelli N, Po KH. L, Chen S, Brady SF, Li X. Angew. Chem. Int. Ed. 2020; 59: 19868
    CrossrefPubMed
  • 16 Chen D, Po KH. L, Blasco P, Chen S, Li X. Org. Lett. 2020; 22: 4749
    CrossrefPubMed
  • 17 Wang J, Lin D, Liu M, Liu H, Blasco P, Sun Z, Cheung YC, Chen S, Li X. J. Am. Chem. Soc. 2021; 143: 12784
    CrossrefPubMed
  • 18 Xu C, Xu J, Liu H, Li X. Chin. Chem. Lett. 2018; 29: 1119
    CrossrefPubMed
  • 19 Fukuda DS, Bus RH. D, Baker PJ, Berry DM, Mynderse JS. J. Antibiot. 1990; 43: 594
    CrossrefPubMed
  • 20 Chen D, Chow HY, Po KH. L, Ma W, Leung EL. Y, Sun Z, Liu M, Chen S, Li X. Org. Lett. 2019; 21: 5639
    CrossrefPubMed
  • 21 Theuretzbacher U, Bush K, Harbarth S, Paul M, Rex JH, Tacconelli E, Thwaites GE. Nat. Rev. Microbiol. 2020; 18: 286
    CrossrefPubMed
  • 22 Nguyen KT, Ritz D, Gu J.-Q, Alexander D, Chu M, Miao V, Brian P, Baltz RH. Proc. Natl. Acad. Sci. U.S.A. 2006; 103: 17462
    CrossrefPubMed
  • 23 Yin N, Li J, He Y, Herradura P, Pearson A, Mesleh MF, Mascio CT, Howland K, Steenbergen J, Thorne GM, Citron D, Van Praagh AD. G, Mortin LI, Keith D, Silverman J, Metcalf C. J. Med. Chem. 2015; 58: 5137
    CrossrefPubMed
    • 24a Chow HY, Po KH. L, Jin K, Qiao G, Sun Z, Ma W, Ye X, Zhou N, Chen S, Li X. ACS Med. Chem. Lett. 2020; 11: 1442
      CrossrefPubMed
    • 24b Lin D, Lam HY, Han W, Cotroneo N, Pandya BA, Li X. Bioorg. Med. Chem. Lett. 2017; 27: 456
      CrossrefPubMed
  • 25 Karas JA, Carter GP, Howden BP, Turner AM, Paulin OK. A, Swarbrick JD, Baker MA, Li J, Velkov T. J. Med. Chem. 2020; 63: 13266
    CrossrefPubMed
  • 26 Chow HY, Po KH. L, Gao P, Blasco P, Wang X, Li C, Ye L, Jin K, Chen K, Chan EW. C, You X, Kao RY. T, Chen S, Li X. J. Med. Chem. 2020; 63: 3161
    CrossrefPubMed
  • 27 Blasco P, Zhang C, Chow HY, Chen G, Wu Y, Li X. Biochim. Biophys. Acta Gen. Subj. 2021; 1865: 129918
    CrossrefPubMed
  • 28 Po KH. L, Chow HY, Cheng Q, Chan BK.-W, Deng X, Wang S, Chan EW. C, Kong H.-K, Chan KF, Li X, Chen S. Nat. Sci. 2021; e10023; DOI: DOI: 10.1002/ntls.10023.
    Crossref