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Total Synthesis of Chondramide C and Its Binding Mode to F‐Actin
Author(s) -
Waldmann Herbert,
Hu TaiShan,
Renner Steffen,
Menninger Sascha,
Tannert René,
Oda Toshiro,
Arndt HansDieter
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200801010
Subject(s) - actin , protein filament , chemistry , polyketide , metathesis , computational biology , stereochemistry , computer science , docking (animal) , polymerization , biology , biochemistry , polymer , gene , organic chemistry , biosynthesis , medicine , nursing
Actin glue: An E ‐selective ring‐closing metathesis as the key step allowed the solid‐phase‐based total synthesis of the F‐actin stabilizer chondramide C as well as the establishment of its hitherto unknown stereochemistry. A strong influence of the polyketide configuration was revealed in cellular assays. Docking studies on the F‐actin filament structure led to a detailed model of the binding site.