Total synthesis of proposed structure of coibamide A,a highly N- and O-methylated cytotoxic marine cyclodepsipeptide |
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| Authors: | Wei He Hai-Bo Qiu Yi-Jie Chen Jie Xi Zhu-Jun Yao |
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| Affiliation: | 1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China;2. State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, 22 Hankou Road, Nanjing, Jiangsu 210093, China |
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| Abstract: | Total synthesis of the originally proposed structure of coibamide A, a highly N- and O-methylated cytotoxic marine cyclodepsipeptide, has been accomplished by using a [(4+1)+3+3]-peptide fragment-coupling strategy and careful examination and optimization of the multiple dense N-methylated amide-bond formations. The synthetic sample of the proposed coibamide A could not match the natural product in both 1H and 13C NMR spectra, but was found to exhibit low micromolar cytotoxicity against the proliferation of three tested cancer cells. |
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| Keywords: | Coibamide A Cyclodepsipeptide Anticancer N-Methylamino acid Total synthesis |
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