Organic Letters
Organic Letters
5 years ago

Total Synthesis and Stereochemical Assignment of Gymnopeptides A and B

Total Synthesis and Stereochemical Assignment of Gymnopeptides A and B
Hongchang Li, Ke Liu, Lijing Fang, Wei Wang, Zhengyin Pan, Guiyang Yao, Chunlei Wu, Zhehong Cheng, Wu Su
Gymnopeptides A and B are unprecedented highly N-methylated cyclic β-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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01742

DOI: 10.1021/acs.orglett.7b01742

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