761444-83-1

Upstream product

• 1124235-00-2 C₄₄H₆₇N₅O₁₀ 
• 1075710-19-8 C₃₀H₄₅Cl₃N₄O₇ 
• 1075710-29-0 C₆₃H₈₄Cl₃N₅O₁₃S 
• 1352449-26-3 C₆₁H₈₃N₅O₁₃S 
• 1075710-30-3 C₄₆H₇₃N₅O₁₁S 
• 1009642-79-8 C₄₆H₇₁N₅O₁₀S 
• 1239981-42-0 C₁₃H₂₂Cl₃NO₄ 
• 1075710-16-5 C₁₆H₂₇Cl₃N₂O₅ 
• 1239981-43-1 C₁₁H₁₉Cl₃N₂O₃*ClH 
• 1075710-17-6 C₂₆H₃₈Cl₃N₃O₆ 
• 1239985-33-1 C₂₁H₃₀Cl₃N₃O₄*ClH 
• 1075710-18-7 C₂₉H₄₃Cl₃N₄O₇ 
• 1352449-33-2 C₂₄H₃₅Cl₃N₄O₅*ClH 
• 1075710-20-1 C₅₁H₈₃Cl₃N₄O₁₀SSi 

Relevant academic research and scientific papers

The total synthesis and structure-activity relationships of a highly cytotoxic depsipeptide kulokekahilide-2 and its analogs

We successfully completed the total synthesis of kulokekahilide-2, a cytotoxic depsipeptide from the Cephalaspiedean mollusk Phillinopsis speciosa. We have revised the absolute stereochemistry of kulokekahilide-2 to 21-l-Ala, 24-d-MePhe, 37-l-Ile, 43-d-Ala, 15-d-Hica, and 5S,6S,7S-Dtda. We also investigated the cause of the mis-assignment of the configuration in the originally proposed kulokekahilide-2 and concluded that methanolysis using MeONa caused partial racemization, which led to the mis-assignment. The structure-activity relationships of kulokekahilide-2 and its analogs indicate the importance of an l-amino acid at position 21.

Intramolecular ester exchange of potent cytotoxic kulokekahilide-2

Kulokekahilide-2 is a 26-membered cyclic depsipeptide that exhibits potent cytotoxicity against HeLa and P388 cells with IC50 values of 3.2 and 16 ng/mL, respectively. We have achieved a total synthesis of natural kulokekahilide-2, the NMR spectra of which showed complex signals because of trans and cis conformers at the amide bond. Besides, the spectra revealed that a mixture of 26- and 24-membered cyclic depsipeptides had been produced due to intramolecular ester exchange. The isolated 24-membered compound was transformed into the 26-membered compound over a period of several days. The two isomers have been shown to be in equilibrium and to display almost the same cytotoxicity.