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

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 derivat...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2012-06, Vol.8 (1), p.861-869
Main Authors: Knobloch, Tobias, Dräger, Gerald, Collisi, Wera, Sasse, Florenz, Kirschning, Andreas
Format: Article
Language:English
Subjects:
ansamitocins
antibiotics
antitumor agents
Chemistry
Full Research Paper
mutasynthesis
natural products
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Summary: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.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.8.96