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

Tobias Knobloch, Gerald Dräger, Wera Collisi and 2 more

Beilstein Journal of Organic Chemistry · 2012

doi:10.3762/bjoc.8.96 (opens in a new tab)

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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.

Abstract licence: CC BY

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