Details
| Original language | English |
|---|---|
| Pages (from-to) | 861-869 |
| Number of pages | 9 |
| Journal | Beilstein Journal of Organic Chemistry |
| Volume | 8 |
| Publication status | Published - 11 Jun 2012 |
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
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
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In: Beilstein Journal of Organic Chemistry, Vol. 8, 11.06.2012, p. 861-869.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Unprecedented deoxygenation at C-7 of the ansamitocin core during mutasynthetic biotransformations
AU - Knobloch, Tobias
AU - Dräger, Gerald
AU - Collisi, Wera
AU - Sasse, Florenz
AU - Kirschning, Andreas
PY - 2012/6/11
Y1 - 2012/6/11
N2 - 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.
AB - 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.
KW - Ansamitocins
KW - Antibiotics
KW - Antitumor agents
KW - Mutasynthesis
KW - Natural products
UR - http://www.scopus.com/inward/record.url?scp=84862699472&partnerID=8YFLogxK
U2 - 10.3762/bjoc.8.96
DO - 10.3762/bjoc.8.96
M3 - Article
AN - SCOPUS:84862699472
VL - 8
SP - 861
EP - 869
JO - Beilstein Journal of Organic Chemistry
JF - Beilstein Journal of Organic Chemistry
SN - 1860-5397
ER -