Determination of the Absolute Configuration of Peptide Natural Products by Using Stable Isotope Labeling and Mass Spectrometry

Structure elucidation of natural products including the absolute configuration is a complex task that involves different analytical methods like mass spectrometry, NMR spectroscopy, and chemical derivation, which are usually performed after the isolation of the compound of interest. Here, a combinat...

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Bibliographic Details
Published in:Chemistry : a European journal 2012-02, Vol.18 (8), p.2342-2348
Main Authors: Bode, Helge B., Reimer, Daniela, Fuchs, Sebastian W., Kirchner, Ferdinand, Dauth, Christina, Kegler, Carsten, Lorenzen, Wolfram, Brachmann, Alexander O., Grün, Peter
Format: Article
Language:English
Subjects:
Biological Products - chemistry
Chemistry
configuration determination
Derivation
Games
Isotope Labeling - methods
Isotopes
isotopic labeling
Magnetic Resonance Spectroscopy
Marking
Mass spectrometry
Mass Spectrometry - methods
Natural products
NMR
NMR spectroscopy
Nuclear magnetic resonance
Peptides
Peptides - chemistry
Peptides, Cyclic - chemistry
Scientific imaging
Stereoisomerism
structure elucidation
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Summary:Structure elucidation of natural products including the absolute configuration is a complex task that involves different analytical methods like mass spectrometry, NMR spectroscopy, and chemical derivation, which are usually performed after the isolation of the compound of interest. Here, a combination of stable isotope labeling of Photorhabdus and Xenorhabdus strains and their transaminase mutants followed by detailed MS analysis enabled the structure elucidation of novel cyclopeptides named GameXPeptides including their absolute configuration in crude extracts without their actual isolation. Game over—structure solved: A combination of labeling experiments with mass spectrometry results in the reliable determination of the sum formula, the nature of the building blocks, and (for peptide natural products) also the determination of the absolute configuration as exemplified for the novel natural products GameXPeptide A–D (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201103479