Chinese Journal of Applied Chemistry ›› 2019, Vol. 36 ›› Issue (6): 677-682.DOI: 10.11944/j.issn.1000-0518.2019.06.180364

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Solid-Phase Synthesis of Cyclohexapeptide Thermoactinoamide A and Its Antibacterial Activity

YANG Jin,MA Qiseng,ZHONG Ying,ZHU Longbao(),GE Fei,TAO Yugui,SONG Ping   

  1. School of Biochemical Engineering,Anhui Polytechnic University,Wuhu,Anhui 241000,China
  • Received:2018-11-13 Accepted:2019-01-30 Online:2019-06-01 Published:2019-06-03
  • Contact: ZHU Longbao
  • Supported by:
    Supported by the Natural Sciences Foundation of Anhui Province Universities(No.KJ2017A123), the Anhui Polytechnic University Youth Talent Program(No.2016BJRC006)

Abstract:

A natural antibacterial cyclic peptide thermoactinoamide A was synthesized by solid-liquid phase two-step method. First, based on fluorenylmethoxycarbonyl(Fmoc) solid phase synthesis, the linear peptide was obtained in 84% yield by optimizing the addition of N,N'-diisopropylethylamine(DIPEA). Then the linear peptide was converted to thermoactinoamide A in 51% yield(43% yield total) through optimizing the cyclization conditions. Antibacterial activity test results show that minimum inhibitory concentration of cyclic thermoactinoamide A for Staphylococcus aureus is 32 μg/mL. In summary, an effectively synthetic strategy was developed for further applications of cyclic peptide thermoactinoamide A on analyzing the structure-activity relationship and improving the bioactivity.

Key words: thermoactinoamide A, solid-phase synthesis, cyclic peptide, antibacterial activity