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Molecular Orbital Study of the Losses of CO2 and H2O in the Fast Atom Bombardment Mass Spectra of Polyether Antibiotics

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Abstract:

In an earlier fast atom bombardment mass spectroscopy study of polyether antibiotics containing a β-hemiketal carboxylic acid group, the base peak was found to originate from the unusual fragmentation process where both CO2 and H2O were lost from the metal-adduct molecular ion. In this paper, the details of this fragmentation process are studied by ab initio molecular orbital calculations, which indicate that the concerted loss of both CO2 and H2O is much favored over sequential losses of CO2 and H2O.

Keywords: Decarboxylation; Dehydration; Fast atom bombardment; Maduramicin α; Mass spectroscopy; Molecular orbital calculations; Polyether antibiotics; β-Hemiketal carboxylic acid moiety

Document Type: Research Article

DOI: http://dx.doi.org/10.1366/0003702874447482

Affiliations: 1: American Cyanamid Company, Medical Research Division, Lederle Laboratories, Pearl River, New York 10965 2: American Cyanamid Company, Medical Research Division, Lederle Laboratories, Pearl River, New York 10965; home address: 71 Strawberry Hill Ave., Apt. 704, Stamford, CT 06902

Publication date: September 1, 1987

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