Structure Elucidation of Macrolide Antibiotics Using MSn Analysis and Deuterium Labelling

Andrew R. Johnson, Erin E. Carlson

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

The 14- and 16-membered macrolide antibiotics are an important structural class. Ubiquitously produced by a number of bacterial strains, namely actinomycetes, purification and structure elucidation of the wide array of analogs is challenging, both for discovery efforts and methodologies to monitor for byproducts, metabolites, and contaminants. Collision-induced dissociation mass spectrometry offers an attractive solution, enabling characterization of mixtures, and providing a wealth of structural information. However, interpretation of these spectra can be difficult. We present a study of 14- and 16-membered macrolide antibiotics, including MSn analysis for unprecedented depth of coverage, and complimentary analysis with D2O and H2 18O labeling to elucidate fragmentation mechanisms. These analyses contrast the behaviors of varying classes of macrolides and highlight how analogues can be identified in relation to similar structures, which will provide utility for future studies of novel macrolides, as well as impurities, metabolites, and degradation products of pharmaceuticals. [Figure not available: see fulltext.].

Original languageEnglish (US)
Pages (from-to)1464-1480
Number of pages17
JournalJournal of the American Society for Mass Spectrometry
Volume30
Issue number8
DOIs
StatePublished - Aug 15 2019

Keywords

  • Macrolide antibiotics
  • Multilevel fragmentation
  • Structure elucidation

PubMed: MeSH publication types

  • Journal Article

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