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Gdańsk University of Technology

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The complete stereochemistry of the antibiotic candicidin A3 (syn. ascosin A3, levorin A3)

Herein, the stereostructure of the aromatic heptaene macrolide (AHM) antifungal antibiotic candicidin A3 (syn. ascosin A3, levorin A3) has been established upon the 2D NMR studies, consisting of DQF-COSY, TOCSY, ROESY, HSQC and HMBC experiments, as well as upon extensive molecular dynamics simulations. The geometry of the heptaenic chromophore was defined as: (22E, 24E, 26Z, 28Z, 30E, 32E, 34E). The previously unreported absolute configuration of the chiral centres of candicidin A3 was established as: (3R,9 R, 11 S, 13 S, 15 R, 17 S, 18 R, 19 S, 21 R, 36 S, 37 R, 38 S, 40 S, 41 S).

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