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Structure and biosynthesis of xenoamicins from entomopathogenic Xenorhabdus.
Chemistry. 2013 Dec 02; 19(49):16772-9.C

Abstract

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 1D and 2D 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.

Authors+Show Affiliations

Goethe-Universität Frankfurt, Department of Molecular Biotechnology, Max-von-Laue-Strasse 9, 60438 Frankfurt am Main (Germany).No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24203528

Citation

Zhou, Qiuqin, et al. "Structure and Biosynthesis of Xenoamicins From Entomopathogenic Xenorhabdus." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 19, no. 49, 2013, pp. 16772-9.
Zhou Q, Grundmann F, Kaiser M, et al. Structure and biosynthesis of xenoamicins from entomopathogenic Xenorhabdus. Chemistry. 2013;19(49):16772-9.
Zhou, Q., Grundmann, F., Kaiser, M., Schiell, M., Gaudriault, S., Batzer, A., Kurz, M., & Bode, H. B. (2013). Structure and biosynthesis of xenoamicins from entomopathogenic Xenorhabdus. Chemistry (Weinheim an Der Bergstrasse, Germany), 19(49), 16772-9. https://doi.org/10.1002/chem.201302481
Zhou Q, et al. Structure and Biosynthesis of Xenoamicins From Entomopathogenic Xenorhabdus. Chemistry. 2013 Dec 2;19(49):16772-9. PubMed PMID: 24203528.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Structure and biosynthesis of xenoamicins from entomopathogenic Xenorhabdus. AU - Zhou,Qiuqin, AU - Grundmann,Florian, AU - Kaiser,Marcel, AU - Schiell,Matthias, AU - Gaudriault,Sophie, AU - Batzer,Andreas, AU - Kurz,Michael, AU - Bode,Helge B, Y1 - 2013/11/07/ PY - 2013/06/27/received PY - 2013/11/9/entrez PY - 2013/11/10/pubmed PY - 2014/7/8/medline KW - biosynthesis KW - natural products KW - peptides KW - structure elucidation SP - 16772 EP - 9 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 19 IS - 49 N2 - 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 1D and 2D 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. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/24203528/Structure_and_biosynthesis_of_xenoamicins_from_entomopathogenic_Xenorhabdus_ L2 - https://doi.org/10.1002/chem.201302481 DB - PRIME DP - Unbound Medicine ER -