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Solid-Phase Synthesis of Cyclic Octapeptide Phakellistatin 15

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Chemistry of Natural Compounds Aims and scope

The total synthesis of a naturally occurring cyclic proline-enriched octapeptide phakellistatin 15, from a marine sponge, where all the amino acids are in L-configuration, was reported. The phakellistatin 15 was synthesized by applying a two-step solid-phase/solution synthesis strategy. The linear octapeptide was assembled by standard Fmoc chemistry on 2-chlorotrityl chloride resin, cleaved off-resin with acetic acid/trifluoroethanol/dichloromethane to keep the side-chain protecting groups intact, and subsequently cyclization was achieved by a solution method. The final product was purified by a preparative RP-HPLC system, and its structure was identified by HR-QTOF-MS, 1H NMR, and 13C NMR.

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Authors and Affiliations

  1. Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Shandong Provincial Key Laboratory of Glycoscience and Glycoengineering, 266003, Qingdao, P. R. China

    Yu-lei Li, Ming-hao Wu, Qi Chang & Xia Zhao

  2. Laboratory for Marine Drugs and Bioproducts of Qingdao National Laboratory for Marine Science and Technology, 266237, Qingdao, P. R. China

    Yu-lei Li, Qi Chang & Xia Zhao

Authors
  1. Yu-lei Li
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  2. Ming-hao Wu
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  3. Qi Chang
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  4. Xia Zhao
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Correspondence to Xia Zhao.

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Published in Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2019, pp. 448–451.

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Li, Yl., Wu, Mh., Chang, Q. et al. Solid-Phase Synthesis of Cyclic Octapeptide Phakellistatin 15. Chem Nat Compd 55, 520–524 (2019). https://doi.org/10.1007/s10600-019-02729-0

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  • DOI: https://doi.org/10.1007/s10600-019-02729-0

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