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Isolation and Total Synthesis of Kirkamide, an Aminocyclitol from an Obligate Leaf Nodule Symbiont.

  • Sieber S Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel (Switzerland).
  • Carlier A Institute of Plant Biology, University of Zürich, Zollikerstrasse 107, 8008 Zürich (Switzerland).
  • Neuburger M Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel (Switzerland).
  • Grabenweger G Agroscope, Reckenholzstrasse 191, 8046 Zürich (Switzerland).
  • Eberl L Institute of Plant Biology, University of Zürich, Zollikerstrasse 107, 8008 Zürich (Switzerland).
  • Gademann K Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel (Switzerland). karl.gademann@unibas.ch.
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  • 2015-06-03
Published in:
  • Angewandte Chemie (International ed. in English). - 2015
aminocyclitols
ecology
natural products
symbiosis
total synthesis
Biological Products
Burkholderia
Crystallography, X-Ray
Cyclitols
Cyclohexylamines
Methylation
Models, Molecular
Palladium
Plant Leaves
Psychotria
Symbiosis
English The new C7N aminocyclitol kirkamide (1) was isolated from leaf nodules of the plant Psychotria kirkii by using a genome-driven (1)H NMR-guided fractionation approach. The structure and absolute configuration were elucidated by HRMS, NMR, and single-crystal X-ray crystallography. An enantioselective total synthesis was developed, which delivered kirkamide (1) on a gram scale in 11 steps and features a Ferrier carbocyclization and a Pd-mediated hydroxymethylation. We propose that kirkamide is synthesized by Candidatus Burkholderia kirkii, the obligate leaf symbiont of Psychotria kirkii. Kirkamide (1) was shown to be toxic to aquatic arthropods and insects, thus suggesting that bacterial secondary metabolites play a protective role in the Psychotria/Burkholderia leaf nodule symbiosis.
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  • English
Open access status
green
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Persistent URL
https://folia.unifr.ch/unifr/documents/298451
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