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

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.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0004-4757-B Version Permalink: https://hdl.handle.net/21.11116/0000-0009-30C9-E
Genre: Journal Article

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BOL716s1.pdf (Supplementary material), 17MB
 
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 Creators:
Dolke, Franziska1, 2, Author           
Dong, Chuanfu1, Author           
Bandi, Siva, Author
Paetz, Christian3, Author           
Glauser, Gaétan, Author
von Reuß, Stephan H.1, Author           
Affiliations:
1Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society, ou_24028              
2IMPRS on Ecological Interactions, MPI for Chemical Ecology, Max Planck Society, Jena, DE, ou_421900              
3Research Group Biosynthesis / NMR, MPI for Chemical Ecology, Max Planck Society, ou_421898              

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 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.

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 Dates: 20192019-07-152019
 Publication Status: Issued
 Pages: -
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 Identifiers: Other: BOL716
DOI: 10.1021/acs.orglett.9b01914
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Title: Organic Letters
  Other : Org. Lett.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 21 (15) Sequence Number: - Start / End Page: 5832 - 5837 Identifier: ISSN: 1523-7060
CoNE: https://pure.mpg.de/cone/journals/resource/954925626338