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Orthogonal Method for Double-Bond Placement via Ozone-Induced Dissociation Mass Spectrometry (OzID-MS)
journal contribution
posted on 2019-12-10, 21:44 authored by Sonja
L. Knowles, Ngoc Vu, Daniel A. Todd, Huzefa A. Raja, Antonis Rokas, Qibin Zhang, Nicholas H. OberliesMost often, the structures of secondary metabolites are
solved using a suite of NMR techniques. However, there are times when
it can be challenging to position double bonds, particularly those
that are fully substituted or when there are multiple double bonds
in similar chemical environments. Ozone-induced dissociation mass
spectrometry (OzID-MS) serves as an orthogonal structure elucidation
tool, using predictable fragmentation patterns that are generated
after ozonolysis across a carbon–carbon double bond. This technique
is finding growing use in the lipidomics community, suggestive of
its potential value for secondary metabolites. This methodology was
evaluated by confirming the double-bond positions in five fungal secondary
metabolites, specifically, ent-sartorypyrone E (1), sartorypyrone A (2), sorbicillin (3), trichodermic acid A (4), and AA03390 (5). This demonstrated its potential with a variety of chemotypes,
ranging from polyketides to terpenoids and including those in both
conjugated and nonconjugated polyenes. In addition, the potential
of using this methodology in the context of a mixture was piloted
by studying Aspergillus fischeri, first examining
a traditional extract and then sampling a live fungal culture in situ. While the intensity of signals varied from pure
compound to extract to in situ, the utility of the
technique was preserved.
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Keywords
Double-Bond PlacementOzone-Induced Dissociation Mass Spectrometrydouble-bond positionslipidomics communityOzID-MSmetabolitenonconjugated polyenesAA 03390orthogonal structure elucidation toolchemical environmentsOrthogonal MethodAspergillus fischerimethodologyfragmentation patternsOzone-induced dissociation mass spectrometrysartorypyrone ENMR techniques
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