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Structural characterization of polyketides using high mass accuracy tandem mass spectrometry
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Wills, Rebecca, Tosin, Manuela and O’Connor, Peter B. (2012) Structural characterization of polyketides using high mass accuracy tandem mass spectrometry. Analytical Chemistry, Volume 84 (Number 20). pp. 8863-8870. doi:10.1021/ac3022778
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Official URL: http://dx.doi.org/10.1021/ac3022778
Abstract
The tandem mass spectrometry techniques electron-induced dissociation (EID) and collision-activated dissociation (CAD) have been compared as tools for providing detailed structural information of polyketides. Polyketides are an important class of natural products that account for a significant proportion of the drugs currently in clinical use. Three polyketide natural products, namely erythromycin A, lasalocid A, and iso-lasalocid A, were subjected to both CAD and EID, and their fragment ions were assigned with sub-part-per-million accuracy. The number of fragment ions detected through EID was much greater than for CAD, leading to a greater amount of structural information obtained for each polyketide, albeit with a decreased signal-to-noise ratio. The effect of different bound cations on the fragment pattern of the isomers lasalocid A and iso-lasalocid A was studied, with CAD and EID performed on the [M + H]+, [M + Na]+, [M + Li]+, and [M + NH4]+ precursor ions. The lithiated species were found to produce the greatest degree of fragmentation and enabled detailed structural information on the isomers to be obtained. Multistage mass spectrometry (MS3) experiments, combining CAD and EID, could also be performed on the lithiated species, generating new fragment information which enables the two isomers to be distinguished. Combining CAD and EID for the structural characterization of polyketides will therefore be a useful tool for identifying and characterizing unknown polyketides and their biosynthetic intermediates.
| Item Type: | Journal Article | ||||
|---|---|---|---|---|---|
| Divisions: | Faculty of Science > Chemistry | ||||
| Journal or Publication Title: | Analytical Chemistry | ||||
| Publisher: | American Chemical Society | ||||
| ISSN: | 0003-2700 | ||||
| Official Date: | 2012 | ||||
| Dates: |
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| Volume: | Volume 84 | ||||
| Number: | Number 20 | ||||
| Page Range: | pp. 8863-8870 | ||||
| DOI: | 10.1021/ac3022778 | ||||
| Status: | Peer Reviewed | ||||
| Publication Status: | Published | ||||
| Access rights to Published version: | Restricted or Subscription Access |
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