Abstract

European Journal of Mass Spectrometry
Volume 15 Issue 2, Pages 73–81 (2009)
doi: 10.1255/ejms.948

Characterisation of anthracyclines from a cosmomycin D-producing species of Streptomyces by collisionally-activated dissociation and ion mobility mass spectrometry

Celine Kelso,^a Juan Diego Rojas,^b Renata L.A. Furlan,^b Gabriel Padilla,^b,c and Jennifer L. Beck,^a
aSchool of Chemistry, University of Wollongong, New South Wales, Australia 2522. E-mail: jbeck@uow.edu.au
^bInstitute of Biomedical Sciences, University of São Paulo, São Paulo, SP Brazil
^cSchool of Veterinary and Biomedical Sciences, James Cook University, Queensland, Australia 4811

Cultures of cosmomycin D-producing Streptomyces olindensis ICB20 that were propagated for many generations underwent mutations that resulted in production of a range of related anthracyclines by the bacteria. The anthracyclines that retained the two trisaccharide chains of the parent compound were separated by HPLC. Exact mass determination of these compounds revealed that they differed from cosmomycin D (CosD) in that they contained one to three fewer oxygen atoms (loss of hydroxyl groups). Some of the anthracyclines that were separated by HPLC had the same mass. The location from which the hydroxyl groups had been lost relative to CosD (on the aglycone and/or on the sugar residues) was probed by collisionally- activated dissociation using an electrospray ionisation linear quadrupole ion trap mass spectrometer. The presence of anthracyclines with the same mass, but different structure, was confirmed using an electrospray ionisation travelling wave ion mobility mass spectrometer.

Keywords: anthracycline, linear quadrupole ion trap, MSⁿ, travelling wave, ion mobility, electrospray ionisation mass spectrometry, collisionally-activated dissociation

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