Details
| Original language | English |
|---|---|
| Pages (from-to) | 1961-1983 |
| Number of pages | 23 |
| Journal | Synthesis (Germany) |
| Volume | 55 |
| Issue number | 13 |
| Early online date | 16 Jan 2023 |
| Publication status | Published - Jul 2023 |
Abstract
The total synthesis of a series of new carolacton derivatives that mainly lack selected methyl substituents along the polyketide backbone is reported. Their inhibitory activity towards bacterial biofilms revealed that selective removal of the methyl group at C10 does not have a major effect on biological activity, whereas additional removal of the methyl group at C14 in carolacton results in a large decrease in antibacterial activity. A key new feature of this work is the replacement of the Nozaki Hiyama Kishi (NHK) vinylation with a titanium-mediated protocol for the fusion of the two main fragments.
Keywords
- antibiotics, biofilms, carolacton, Nozaki-Hiyama-Kishi reaction, polyketides, structure-activity relationship studies, total synthesis
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Synthesis (Germany), Vol. 55, No. 13, 07.2023, p. 1961-1983.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - New Demethylated Derivatives of Carolacton and Structure-Activity Relationship (SAR) Studies on Their Biofilm Inhibitory Properties
AU - Ammermann, Jonas
AU - Meyer, Janina
AU - Donner, Jannik
AU - Reck, Michael
AU - Wagner-Döbler, Irene
AU - Kirschning, Andreas
N1 - Funding Information: This work has been carried out as an integral part of the Biofabrication for NIFE Initiative, which is financially supported by the Niedersächsisches Ministerium für Wissenschaft und Kultur (MWK, Lower Saxony Ministry of Science and Culture) and the Volkswagen Foundation. We thank Dr. G. Dräger (Leibniz University Hannover) and Dr. J. Fohrer (Technical University Darmstadt) for expert MS and NMR support and advice.
PY - 2023/7
Y1 - 2023/7
N2 - The total synthesis of a series of new carolacton derivatives that mainly lack selected methyl substituents along the polyketide backbone is reported. Their inhibitory activity towards bacterial biofilms revealed that selective removal of the methyl group at C10 does not have a major effect on biological activity, whereas additional removal of the methyl group at C14 in carolacton results in a large decrease in antibacterial activity. A key new feature of this work is the replacement of the Nozaki Hiyama Kishi (NHK) vinylation with a titanium-mediated protocol for the fusion of the two main fragments.
AB - The total synthesis of a series of new carolacton derivatives that mainly lack selected methyl substituents along the polyketide backbone is reported. Their inhibitory activity towards bacterial biofilms revealed that selective removal of the methyl group at C10 does not have a major effect on biological activity, whereas additional removal of the methyl group at C14 in carolacton results in a large decrease in antibacterial activity. A key new feature of this work is the replacement of the Nozaki Hiyama Kishi (NHK) vinylation with a titanium-mediated protocol for the fusion of the two main fragments.
KW - antibiotics
KW - biofilms
KW - carolacton
KW - Nozaki-Hiyama-Kishi reaction
KW - polyketides
KW - structure-activity relationship studies
KW - total synthesis
UR - http://www.scopus.com/inward/record.url?scp=85160962782&partnerID=8YFLogxK
U2 - 10.1055/a-2013-9333
DO - 10.1055/a-2013-9333
M3 - Article
AN - SCOPUS:85160962782
VL - 55
SP - 1961
EP - 1983
JO - Synthesis (Germany)
JF - Synthesis (Germany)
SN - 0039-7881
IS - 13
ER -