Structure and biosynthesis of xenoamicins from entomopathogenic xenorhabdus

Zhou, Qiuqin and Grundmann, Florian and Kaiser, Marcel and Schiell, Matthias and Gaudriault, Sophie and Batzer, Andreas and Kurz, Michael and Bode, Helge B.. (2013) Structure and biosynthesis of xenoamicins from entomopathogenic xenorhabdus. Chemistry : a European journal, Vol. 19, H. 49. pp. 16772-16779.

Full text not available from this repository.

Official URL: http://edoc.unibas.ch/dok/A6211925

Downloads: Statistics Overview


During the search for novel natural products from entomopathogenic Xenorhabdus doucetiae DSM17909 and X. mauleonii DSM17908 novel peptides named xenoamicins were identified in addition to the already known antibiotics xenocoumacin and xenorhabdin. Xenoamicins are acylated tridecadepsipeptides consisting of mainly hydrophobic amino acids. The main derivative xenoamicin A (1) was isolated from X. mauleonii DSM17908, and its structure elucidated by detailed 1 D and 2 D NMR experiments. Detailed MS experiments, also in combination with labeling experiments, confirmed the determined structure and allowed structure elucidation of additional derivatives. Moreover, the xenoamicin biosynthesis gene cluster was identified and analyzed in X. doucetiae DSM17909, and its participation in xenoamicin biosynthesis was confirmed by mutagenesis. Advanced Marfey's analysis of 1 showed that the absolute configuration of the amino acids is in agreement with the predicted stereochemistry deduced from the nonribosomal peptide synthetase XabABCD. Biological testing revealed activity of 1 against Plasmodium falciparum and other neglected tropical diseases but no antibacterial activity.
Faculties and Departments:09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH)
09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) > Department of Medical Parasitology and Infection Biology (MPI) > Parasite Chemotherapy (Mäser)
UniBasel Contributors:Kaiser, Marcel
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Wiley-VCH Verlag
Note:Publication type according to Uni Basel Research Database: Journal article
Related URLs:
Identification Number:
Last Modified:27 Mar 2014 13:12
Deposited On:27 Mar 2014 13:12

Repository Staff Only: item control page