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Light-Induced Transformation of the Aromatic Heptaene Antifungal Antibiotic Candicidin D into Its All-Trans Isomer
Abstract
Illumination of the aromatic heptaene macrolide antifungal antibiotic candicicin D with UV light results in an isomerization of the molecule. The product formed after irradiation of the candicidin complex with UV light (λ=365nm), namely, iso-candicidin D, was isolated and subjected to 2D NMR studies, consisting of DQF-COSY, ROESY, TOCSY, HSQC, and HMBC experiments. The obtained spectral data unambiguously evidenced that iso-candicidin D was the alltrans isomer of the native antibiotic, and straightening of the heptaenic chromophore was the only light-induced structural change that occurred. Hence, iso-candicidin D was proclaimed to be a prototype of a novel class of polyene macrolide antifungal antibiotics: the all-trans aromatic heptaenes, containing a macrolide ring similar to that of amphotericin B.
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- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
JOURNAL OF NATURAL PRODUCTS
no. 81,
edition 7,
pages 1540 - 1545,
ISSN: 0163-3864 - Language:
- English
- Publication year:
- 2018
- Bibliographic description:
- Szczeblewski P., Laskowski T., Bałka A., Borowski E., Milewski S.: Light-Induced Transformation of the Aromatic Heptaene Antifungal Antibiotic Candicidin D into Its All-Trans Isomer// JOURNAL OF NATURAL PRODUCTS. -Vol. 81, iss. 7 (2018), s.1540-1545
- DOI:
- Digital Object Identifier (open in new tab) 10.1021/acs.jnatprod.7b00821
- Verified by:
- Gdańsk University of Technology
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