Abstract
Analysis of commercial spectinomycin samples with ion-pairing reversed-phase LC coupled with electrospray ionization tandem MS (LC/ESI-MS/MS) indicates that eight additional compounds are present, including actinamine, (4R)-dihydrospectinomycin, (4S)-dihydrospectinomycin and dihydroxyspectinomycin, as well as four new impurities reported, to our knowledge, for the first time. The structures of these compounds were elucidated by comparing their fragmentation patterns with known structures, and NMR was employed to characterize and distinguish (4R)-dihydrospectinomycin and (4S)-dihydrospectinomycin. Identification of dihydrospectinomycin isomers is necessary because (4R)-dihydrospectinomycin is a minor active pharmaceutical ingredient of spectinomycin, whereas (4S)-dihydrospectinomycin is considered to be an impurity (impurity C) by the European Pharmacopoeia (Ph. Eur.).
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Acknowledgements
This article was supported by the Youth Development Research Foundation of NIFDC (Project No. 7030230111102). We acknowledge Yi Wang from Ge Rui High Technology (Hebei, China) for preparation of dihydrospectinomycin, Yaozuo Yuan from the Jiangsu Institute for Food and Drug Control (Jiangsu, China) for providing help in the fragmentation pattern of spectinomycin and Erwin Adams from KU Leuven for many helpful suggestions on the modification of the manuscript.
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Wang, Y., Wang, M., Li, J. et al. Characterization of impurities in commercial spectinomycin by liquid chromatography with electrospray ionization tandem mass spectrometry. J Antibiot 67, 511–518 (2014). https://doi.org/10.1038/ja.2014.32
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DOI: https://doi.org/10.1038/ja.2014.32
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