Ascaroside signaling in the bacterivorous nematode Caenorhabditis remanei 
encodes the growth phase of its bacterial food source

Dolke, Franziska; Dong, Chuanfu; Bandi, Siva; Paetz, Christian; Glauser, Gaétan; von Reuß, Stephan H.

doi:10.1021/acs.orglett.9b01914

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Ascaroside signaling in the bacterivorous nematode Caenorhabditis remanei encodes the growth phase of its bacterial food source

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Dolke, Franziska
Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society;
IMPRS on Ecological Interactions, MPI for Chemical Ecology, Max Planck Society;

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Dong, Chuanfu
Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society;

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Paetz, Christian
Research Group Biosynthesis / NMR, MPI for Chemical Ecology, Max Planck Society;

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von Reuß, Stephan H.
Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society;

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Citation

Dolke, F., Dong, C., Bandi, S., Paetz, C., Glauser, G., & von Reuß, S. H. (2019). Ascaroside signaling in the bacterivorous nematode Caenorhabditis remanei encodes the growth phase of its bacterial food source. Organic Letters, 21(15), 5832-5837. doi:10.1021/acs.orglett.9b01914.

Cite as: https://hdl.handle.net/21.11116/0000-0004-4757-B

Abstract

A novel class of species-specific modular ascarosides
that integrate additional fatty acid building blocks was
characterized in the nematode Caenorhabditis remanei using a
combination of HPLC−ESI−(−)-MS/MS precursor ion
scanning, microreactions, HR-MS/MS, MSn, and NMR
techniques. The structure of the dominating component
carrying a cyclopropyl fatty acid moiety was established by
total synthesis. Biogenesis of this female-produced male
attractant depends on cyclopropyl fatty acid synthase (cfa),
which is expressed in bacteria upon entering their stationary phase.