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

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,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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Category:
Articles
Type:
artykuł w czasopiśmie wyróżnionym w JCR
Published in:
NATURAL PRODUCT RESEARCH no. 34, pages 2869 - 2879,
ISSN: 1478-6419
Language:
English
Publication year:
2019
Bibliographic description:
Borzyszkowska-Bukowska J., Szczeblewski P., KONKOL A., GRYNDA J., Szwarc-Karabyka K., Laskowski T.: The complete stereochemistry of the antibiotic candicidin A3 (syn. ascosin A3, levorin A3)// NATURAL PRODUCT RESEARCH. -Vol. 34, iss. 20 (2019), s.2869-2879
DOI:
Digital Object Identifier (open in new tab) 10.1080/14786419.2019.1596095
Sources of funding:
Verified by:
Gdańsk University of Technology

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