Total synthesis and cytotoxicity studies of a cyclic depsipeptide with proposed structure of palau'amide.
[structure: see text] Total synthesis of a cyclic depsipeptide with proposed structure of palau'amide is achieved, which features a stereoselective elaboration of its 5,7-dihydroxy-2,6-dimethyldodec-2-en-11-ynoic acid unit. The synthetic compound has potent cytotoxicity against three tumor cell lines but different rotation and NMR data compared to those reported for palau'amide, which implies that its conformation is close to that of palau'amide but that some stereochemistry in palau'amide was misassigned.
Zou
Bin
B
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Long
Kai
K
Ma
Dawei
D
D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D006801:Humans; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000737:chemistry*
D047630:Depsipeptides; D010456:Peptides, Cyclic; C482752:palauamide