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Isolation and total synthesis of kirkamide, an aminocyclitol from an obligate leaf nodule symbiont


Sieber, Simon; Carlier, Aurélien; Neuburger, Markus; Grabenweger, Giselher; Eberl, Leo; Gademann, Karl (2015). Isolation and total synthesis of kirkamide, an aminocyclitol from an obligate leaf nodule symbiont. Angewandte Chemie Internationale Edition, 54(27):7968-7970.

Abstract

The new C7N aminocyclitol kirkamide (1) was isolated from leaf nodules of the plant Psychotria kirkii by using a genome-driven 1H 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.

Abstract

The new C7N aminocyclitol kirkamide (1) was isolated from leaf nodules of the plant Psychotria kirkii by using a genome-driven 1H 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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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Plant and Microbial Biology
Dewey Decimal Classification:580 Plants (Botany)
Scopus Subject Areas:Physical Sciences > Catalysis
Physical Sciences > General Chemistry
Uncontrolled Keywords:General Chemistry, Catalysis
Language:English
Date:2015
Deposited On:08 Feb 2016 14:29
Last Modified:14 Jan 2021 10:55
Publisher:Wiley-VCH Verlag
ISSN:1433-7851
OA Status:Green
Publisher DOI:https://doi.org/10.1002/anie.201502696
Project Information:
  • : FunderSNSF
  • : Grant IDCRSII3_154430
  • : Project TitleInvestigations on the obligate leave nodule symbiosis
  • : FunderSNSF
  • : Grant ID206021_150760
  • : Project TitleStudies in the Molecular Sciences Enabled by High Sensitivity NMR

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