1. Isolation and Total Synthesis of Kirkamide, an Aminocyclitol from an Obligate Leaf Nodule Symbiont.
- Author
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Sieber, Simon, Carlier, Aurélien, Neuburger, Markus, Grabenweger, Giselher, Eberl, Leo, and Gademann, Karl
- Subjects
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BURKHOLDERIA , *BURKHOLDERIA infections , *X-ray crystallography , *CANDIDATUS , *METABOLITES , *SYMBIOSIS , *ARTHROPODA - 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 FROM AUTHOR]
- Published
- 2015
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