Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 6, Pages 1806-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja7110064
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A novel cytotoxic cyclodepsipeptide, termed largazole (1), has been isolated from the marine cyanobacterium Symploca sp. collected in the Florida Keys. Its planar structure was elucidated by 1 D and 2D NMR spectroscopy in conjunction with mass spectrometry. The absolute configuration of I was determined by chemical degradation followed by chiral HPLC analysis. Largazole (1) possesses densely assembled unusual structural features, including a rare 4-methylthiazoline linearly fused to a thiazole in its cyclic core and a hitherto undescribed 3-hydroxy-7-mercaptohept-4-enoic acid unit incorporated in an ester, thioester, and amide framework. Largazole (1) exhibits potent antiproliferative activity and preferentially targets cancer cells over nontransformed cells.
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