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Mitsunobu-Reaction-Based Total Solid-Phase Synthesis of Fanlizhicyclopeptide B

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Chemistry of Natural Compounds Aims and scope

The first total synthesis of anti-inflammatory cyclic peptide fanlizhicyclopeptide B based on the Mitsunobu reaction is reported. The pre-made Fmoc-Tyr-OAllyl building block was coupled to the Wang resin via the Mitsunobu reaction catalyzed by triphenylphosphine and diethyl azodicarboxylate. After the remaining amino acids were assembled, macrocyclization was realized on solid support. Finally, the crude product was cleaved from resin and then purified by preparative reverse-phase high-performance liquid chromatography (RP-HPLC) to provide the pure target fanlizhicyclopeptide B.

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Acknowledgment

We are grateful to the Instrumental Analysis Center of the Second Military Medical University for NMR spectroscopic and mass spectrometric analysis.

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Authors and Affiliations

  1. Shanghai Pudong New Area People′s Hospital, 201299, Shanghai, P. R. China

    Wen Cui

  2. School of Pharmacy, Second Military Medical University, 200433, Shanghai, P. R. China

    Chao Liu & Xiao-Bin Zhuo

Authors
  1. Wen Cui
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  2. Chao Liu
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  3. Xiao-Bin Zhuo
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Corresponding author

Correspondence to Xiao-Bin Zhuo.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2021, pp. 930–932.

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Cui, W., Liu, C. & Zhuo, XB. Mitsunobu-Reaction-Based Total Solid-Phase Synthesis of Fanlizhicyclopeptide B. Chem Nat Compd 57, 1086–1089 (2021). https://doi.org/10.1007/s10600-021-03554-0

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  • DOI: https://doi.org/10.1007/s10600-021-03554-0

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