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First total synthesis of antifungal cyclopeptide tunicyclin d by a solid-phase method

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Chemistry of Natural Compounds Aims and scope

The present study deals with the first total synthesis of a new antifungal cyclic octapeptide, tunicyclin D, cyclo[VNIPPWHG], where all the amino acids are L-configuration, by a two-step solid-phase/solution synthesis strategy. The linear octapeptide was assembled by a solid-phase peptide synthesis (SPPS) method. Subsequently cyclization and deprotection were achieved in solution with high efficiency and reproducibility. The final product was purified by preparative RP-HPLC, and its structure was identified by ESI-MS, 1 H NMR, 13 C NMR, and HR-QTOF-MS.

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Acknowledgment

We are grateful to the National Natural Science Foundation of China (No. 20902109) and Instrumental Analysis Center of our University for NMR spectrum and mass spectrometric analyses.

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Authors and Affiliations

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

    Jun-xiang Guo, Chun-mei Zhang, Gen-jin Yang & Hong-gang Hu

  2. Fengxian Central Hospital, 201400, Shanghai, P. R. China

    Wei-feng Wu

  3. Changhai Hospital, Second Military Medical University, 200433, Shanghai, P. R. China

    Ming Juan Xu

Authors
  1. Jun-xiang Guo
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  2. Wei-feng Wu
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  3. Chun-mei Zhang
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  4. Gen-jin Yang
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  5. Ming Juan Xu
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  6. Hong-gang Hu
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Corresponding author

Correspondence to Ming Juan Xu.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2012, pp. 404–406.

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Guo, Jx., Wu, Wf., Zhang, Cm. et al. First total synthesis of antifungal cyclopeptide tunicyclin d by a solid-phase method. Chem Nat Compd 48, 447–450 (2012). https://doi.org/10.1007/s10600-012-0270-9

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  • DOI: https://doi.org/10.1007/s10600-012-0270-9

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