Fungal biotransformation of tetracycline antibiotics

Shang, Zhuo, Salim, Angela A., Khalil, Zeinab, Bernhardt, Paul V. and Capon, Robert J. (2016) Fungal biotransformation of tetracycline antibiotics. Journal of Organic Chemistry, 81 15: 6186-6194. doi:10.1021/acs.joc.6b01272

Author Shang, Zhuo
Salim, Angela A.
Khalil, Zeinab
Bernhardt, Paul V.
Capon, Robert J.
Title Fungal biotransformation of tetracycline antibiotics
Journal name Journal of Organic Chemistry   Check publisher's open access policy
ISSN 1520-6904
Publication date 2016-08-05
Year available 2016
Sub-type Article (original research)
DOI 10.1021/acs.joc.6b01272
Open Access Status Not yet assessed
Volume 81
Issue 15
Start page 6186
End page 6194
Total pages 9
Place of publication Washington, DC United States
Publisher American Chemical Society
Language eng
Formatted 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.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: HERDC Pre-Audit
School of Chemistry and Molecular Biosciences
Institute for Molecular Bioscience - Publications
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Citation counts: TR Web of Science Citation Count  Cited 1 times in Thomson Reuters Web of Science Article | Citations
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Created: Fri, 09 Sep 2016, 22:02:17 EST by Susan Allen on behalf of Institute for Molecular Bioscience