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Natural Product Research
Formerly Natural Product Letters
Volume 34, 2020 - Issue 20
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Research Articles

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

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Pages 2869-2879 | Received 14 Dec 2018, Accepted 06 Mar 2019, Published online: 09 Apr 2019
 

Abstract

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, 9R, 11S, 13S, 15R, 17S, 18R, 19S, 21R, 36S, 37R, 38S, 40S, 41S).

Graphical Abstract

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

The authors acknowledge their gratitude to the Polish National Science Centre for financial support, Project No. UMO-2016/23/B/NZ7/01223.

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