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Beilstein J Org Chem. 2012;8:861-9. Epub 2012 Jun 11.

Unprecedented deoxygenation at C-7 of the ansamitocin core during mutasynthetic biotransformations.

Author information

  • 1Institute of Organic Chemistry and Center of Biomolecular Drug Research (BMWZ), Leibniz University Hannover, Schneiderberg 1b, 30167 Hannover, Germany.

Abstract

We describe the unprecedented formation of six ansamitocin derivatives that are deoxygenated at C-7 of the ansamitocin core, obtained during fermentation experiments by employing a variety of Actinosynnema pretiosum mutants and mutasynthetic approaches. We suggest that the formation of these derivatives is based on elimination at C-7/C-8 followed by reduction(s) of the intermediate enone. In bioactivity tests, only ansamitocin derivatives bearing an ester side chain at C-3 showed strong antiproliferative activity.

KEYWORDS:

ansamitocins; antibiotics; antitumor agents; mutasynthesis; natural products

PMID:
23015834
[PubMed]
PMCID:
PMC3388874
Free PMC Article

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