Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 52, Pages 17478-17487Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201403979
Keywords
biosynthesis; isotopic labeling; mass spectrometry; natural products; peptides
Categories
Funding
- ERC [311477]
- European Community [602773]
- BMBF
- European Research Council (ERC) [311477] Funding Source: European Research Council (ERC)
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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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