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Characterisation of Taxlllaids A–G; Natural Products from Xenorhabdus indica
Author(s) -
Kronenwerth Max,
Bozhüyük Kenan A. J.,
Kahnt Astrid S.,
Steinhilber Dieter,
Gaudriault Sophie,
Kaiser Marcel,
Bode Helge B.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403979
Subject(s) - adenylylation , stereochemistry , biosynthesis , tyrosine , amino acid , phenylalanine , absolute configuration , chemistry , biology , biochemistry , gene
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.