API-Mass Spectrometry of Polyketides. II: Fragmentation Analysis of 6-Deoxyerythronolide B Analogs

The API-MS spectra of 6-deoxyerythronolide B (6-dEB) and a number of its analogs have been studied to gain information into the fragmentation patterns of 6-deoxyerythronolides under atmospheric pressure ionization conditions. The API-MS spectrum of 6-dEB shows five major families of fragments. The s...

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Bibliographic Details
Published in:Journal of antibiotics 2004/09/25, Vol.57(9), pp.579-589
Main Authors: ASHLEY, GARY W., CARNEY, JOHN R.
Format: Article
Language:English
Subjects:
Atmospheric Pressure
Erythromycin - analogs & derivatives
Erythromycin - analysis
Erythromycin - chemistry
Genetic Engineering
Mass Spectrometry - methods
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Summary:The API-MS spectra of 6-deoxyerythronolide B (6-dEB) and a number of its analogs have been studied to gain information into the fragmentation patterns of 6-deoxyerythronolides under atmospheric pressure ionization conditions. The API-MS spectrum of 6-dEB shows five major families of fragments. The spectra of a series of desmethyl-6-dEBs allow assignment of these fragment families to structural subunits as well as provide information regarding the fragmentation mechanisms. The spectrum of [9-18O]-6-dEB is consistent with loss of the ketone oxygen during the first dehydration, and the spectra of other oxygen-modified analogs implicate the non-obligate formation of a 5, 9-hemiacetal in the initial stages of fragmentation. These results taken together are used to propose a model for the fragmentation of 6-dEB and its analogs under API conditions.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.57.579