We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Isolation and Total Synthesis of Kirkamide, an Aminocyclitol from an Obligate Leaf Nodule Symbiont.
- Authors
Sieber, Simon; Neuburger, Markus; Gademann, Karl; Carlier, Aurélien; Eberl, Leo; Grabenweger, Giselher
- 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.
- Subjects
BIOSYNTHESIS; CYCLITOLS; PLANT ecology; PLANT-bacterial symbiosis; PSYCHOTRIA; BURKHOLDERIA; ENANTIOSELECTIVE catalysis
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 27, p7968
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201502696