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Characterisation of taxlllaids A-G; natural products from Xenorhabdus indica.

Abstract : Six new lipodepsipeptides and an additional linear derivative named taxlllaids A-G (1-7) have been identified in the entomopathogenic bacterium Xenorhabdus indica. The structures of the main compounds have been solved by detailed NMR spectroscopic analysis and the structures of minor derivatives were elucidated by a combination of labelling experiments and detailed MS experiments. The absolute configuration of the taxlllaids was deduced by using the advanced Marfey method and analysis of the biosynthesis gene cluster showing the presence of epimerisation domains, which was subsequently proved to be correct by solid-phase peptide synthesis of all taxlllaids. The exchange of a single amino acid in the adenylation domain was shown to be responsible for substrate promiscuity of the third A domain, resulting in the incorporation of leucine, phenylalanine or tyrosine. Bioactivity testing revealed the taxlllaids to be weakly active against Plasmodium falciparum and against a number of eukaryotic cell lines.
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Déposant : Archive Ouverte Prodinra <>
Soumis le : jeudi 12 juillet 2018 - 20:03:13
Dernière modification le : mardi 20 octobre 2020 - 16:12:04

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Max Kronenwerth, Kenan a J Bozhüyük, Astrid S Kahnt, Dieter Steinhilber, Sophie Gaudriault, et al.. Characterisation of taxlllaids A-G; natural products from Xenorhabdus indica.. Chemistry - A European Journal, Wiley-VCH Verlag, 2014, 20 (52), pp.17478-17487. ⟨10.1002/chem.201403979⟩. ⟨hal-01837276⟩



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