Details
| Original language | English |
|---|---|
| Pages (from-to) | 8029-8036 |
| Number of pages | 8 |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 13 |
| Issue number | 29 |
| Publication status | Published - 7 Aug 2015 |
Abstract
The soraphens are natural products that exhibit a molecular structure different from what would have been expected by following its polyketidal assembly line. The most significant differences are the presence of a hemiketal instead of a trisubstituted double bond and a double bond at C9 and C10 where a saturated carbon chain was expected. We were interested in the biological activity of the soraphens with architectures as described by the polyketide synthase since we hypothesized that these modifications reflect the evolutionary optimization of the soraphens. Herein we describe four additional derivatives of the so-called paleo-soraphens and their biological profiling to provide a picture of the hypothetical evolutionary optimization of this family of natural products. The syntheses required a unified and convergent strategy and their biological profiling was performed with the aid of impedance measurements. The results of these biological experiments are consistent with the proposed evolutionary optimization of the soraphens.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: Organic and Biomolecular Chemistry, Vol. 13, No. 29, 07.08.2015, p. 8029-8036.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Paleo-soraphens
T2 - Chemical total syntheses and biological studies
AU - Lu, Hai Hua
AU - Hinkelmann, Bettina
AU - Tautz, Thomas
AU - Li, Jun
AU - Sasse, Florenz
AU - Franke, Raimo
AU - Kalesse, Markus
N1 - Publisher Copyright: © The Royal Society of Chemistry.
PY - 2015/8/7
Y1 - 2015/8/7
N2 - The soraphens are natural products that exhibit a molecular structure different from what would have been expected by following its polyketidal assembly line. The most significant differences are the presence of a hemiketal instead of a trisubstituted double bond and a double bond at C9 and C10 where a saturated carbon chain was expected. We were interested in the biological activity of the soraphens with architectures as described by the polyketide synthase since we hypothesized that these modifications reflect the evolutionary optimization of the soraphens. Herein we describe four additional derivatives of the so-called paleo-soraphens and their biological profiling to provide a picture of the hypothetical evolutionary optimization of this family of natural products. The syntheses required a unified and convergent strategy and their biological profiling was performed with the aid of impedance measurements. The results of these biological experiments are consistent with the proposed evolutionary optimization of the soraphens.
AB - The soraphens are natural products that exhibit a molecular structure different from what would have been expected by following its polyketidal assembly line. The most significant differences are the presence of a hemiketal instead of a trisubstituted double bond and a double bond at C9 and C10 where a saturated carbon chain was expected. We were interested in the biological activity of the soraphens with architectures as described by the polyketide synthase since we hypothesized that these modifications reflect the evolutionary optimization of the soraphens. Herein we describe four additional derivatives of the so-called paleo-soraphens and their biological profiling to provide a picture of the hypothetical evolutionary optimization of this family of natural products. The syntheses required a unified and convergent strategy and their biological profiling was performed with the aid of impedance measurements. The results of these biological experiments are consistent with the proposed evolutionary optimization of the soraphens.
UR - http://www.scopus.com/inward/record.url?scp=84940426576&partnerID=8YFLogxK
U2 - 10.1039/c5ob01249j
DO - 10.1039/c5ob01249j
M3 - Article
C2 - 26119264
AN - SCOPUS:84940426576
VL - 13
SP - 8029
EP - 8036
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 29
ER -