Characterisation of taxlllaids A-G; natural products from Xenorhabdus indica. - INRAE - Institut national de recherche pour l’agriculture, l’alimentation et l’environnement Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2014

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

Résumé

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.

Dates et versions

hal-01837276 , version 1 (12-07-2018)

Identifiants

Citer

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, 2014, 20 (52), pp.17478-17487. ⟨10.1002/chem.201403979⟩. ⟨hal-01837276⟩
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