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• W3092051256 abstract "Abstract Yaku′amide B ( 1 ) inhibits cancer cell growth through a unique mechanism of action. Compound 1 binds to mitochondrial F o F 1 ‐ATP synthase, inhibits ATP production, and enhances ATP hydrolysis. The presence of one ( E )‐ and two ( Z )‐α,β‐dehydroisoleucines (ΔIle) in the linear 13‐mer sequence is the most unusual structural feature of 1 . To uncover the biological importance of these residues, we synthesized 1 and its seven E / Z isomers 2 – 8 by devising a new divergent solid‐phase strategy. Both the ( E )‐ and ( Z )‐ΔIle residues were stereoselectively constructed by traceless Staudinger ligation on resin to ultimately deliver 1 – 8 . All isomers 2 – 8 displayed effects on the inhibition of cell growth and ATP production, and enhanced ATP hydrolysis, thus indicating that 2 – 8 share the same mode of action as 1 . The least potent isomer, 8 , was isomeric at three ΔIle residues of the most potent 1 . These findings together indicate that the E / Z stereochemistry of the three ΔIle residues controls the magnitude of the biological functions of 1 ." @default.
• W3092051256 created "2020-10-15" @default.
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• W3092051256 date "2020-12-16" @default.
• W3092051256 modified "2023-10-09" @default.
• W3092051256 title "Divergent Solid‐Phase Synthesis and Biological Evaluation of Yaku'amide B and Its Seven <i>E</i> / <i>Z</i> Isomers" @default.
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• W3092051256 doi "https://doi.org/10.1002/chem.202003858" @default.
• W3092051256 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/33022828" @default.
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