Publication

Back to overview

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

Type of publication Peer-reviewed
Publikationsform Original article (peer-reviewed)
Author Carlier Aurelien , Gademann Karl , Sieber Simon , Neuburger Markus , Grabenweger Giselher , Eberl Leo ,
Project Investigations on the obligate leave nodule symbiosis
Show all

Original article (peer-reviewed)

Journal ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Page(s) 7968 - 7970
Title of proceedings ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
DOI 10.1002/anie.201502696

Abstract

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.
-