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. 2017 Aug 21;7:8931. doi: 10.1038/s41598-017-09416-6

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© The Author(s) 2017

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.

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Negative-ion mode fragmentation of nucleoside 5′-monophosphates (NMP). (a) MS/MS spectra of AMP and dAMP and their [¹⁸O]-labelled analogues. Three types of fragments are visible in the spectra: nucleobase derived (marked with blue dots), phosphoribose-derived (purple dots), and phosphate-derived (green dots). Upon¹⁸O-isotopic labelling of phosphate moieties, the m/z values for phosphate- and phosphoribose-derived fragments that retain heavy water shift accordingly. (b) Fragmentation pathways for NMPs, exemplified by adenine nucleotides, proposed based on the interpretation of MS/MS spectra of nucleoside 5′-monophosphates and their ¹⁸O-isotopologues.