Light-Induced Transformation of the Aromatic Heptaene Antifungal Antibiotic Candicidin D into Its All-Trans Isomer - Publication - Bridge of Knowledge

Search

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.

Citations

  • 1 3

    CrossRef

  • 0

    Web of Science

  • 1 3

    Scopus

Cite as

Full text

full text is not available in portal

Keywords

Details

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

seen 110 times

Recommended for you

Meta Tags