Fungal Biotransformation of Tetracycline Antibiotics

Zhuo Shang, Angela A. Salim, Zeinab Khalil, Paul V. Bernhardt, Robert J. Capon

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The commercial antibiotics tetracycline (3), minocycline (4), chlortetracycline (5), oxytetracycline (6), and doxycycline (7) were biotransformed by a marine-derived fungus Paecilomyces sp. to yield seco-cyclines A-H (9-14, 18 and 19) and hemi-cyclines A-E (20-24). Structures were assigned by detailed spectroscopic analysis, and in the case of 10 X-ray crystallography. Parallel mechanisms account for substrate-product specificity, where 3-5 yield seco-cyclines and 6 and 7 yield hemi-cyclines. The susceptibility of 3-7 to fungal biotransformation is indicative of an unexpected potential for tetracycline "degradation" (i.e., antibiotic resistance) in fungal genomes. Significantly, the fungal-derived tetracycline-like viridicatumtoxins are resistant to fungal biotransformation, providing chemical insights that could inform the development of new tetracycline antibiotics resistant to enzymatic degradation.

Original languageEnglish
Pages (from-to)6186-6194
Number of pages9
JournalJournal of Organic Chemistry
Volume81
Issue number15
DOIs
Publication statusPublished - 5 Aug 2016
Externally publishedYes

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