4.8 Article

Total Synthesis and Stereochemical Assignment of Gymnopeptides A and B

Journal

ORGANIC LETTERS
Volume 19, Issue 17, Pages 4420-4423

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b01742

Keywords

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Funding

  1. Shenzhen Sciences & Technology Innovation Council [KQCX2015033117354154, JCYJ20150316143416083, JCYJ20170413165916608, JCYJ20150401150223649, JCYJ20160229204338907]
  2. National Natural Science Foundation of China [21402232, 21672254, 21432003]

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Gymnopeptides A and B are unprecedented highly N-methylated cyclic beta-hairpin octadecapeptides with striking antiproliferative activities isolated from the mushroom Gymnopus fusipes. Using Fmoc-based solid-phase peptide synthesis, followed by macrolactamization of the resulting linear peptides, the first total synthesis of gymnopeptides A and B was successfully achieved in this study. The coupling methods used for the solid-phase synthesis and the cyclization were optimized, and the configuration of the Ser1/Thr1 residue in gymnopeptide A/B was determined to be L.

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