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. 2017 Aug 31;7:10216. doi: 10.1038/s41598-017-10487-8

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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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Modification of sialic acids using carbodiimide coupling on AutoTip. Fetuin protein was modified by p-Toluidine in the presence of EDC after immobilization on the beads (Four AutoTips). Sialylated N-glycan, S2H5N4, was used to monitor completion of p-Toluidine-EDC reaction. Without derivatization, MALDI-MS detected no sialic acid H5N4 (a) and two sialic acids S2H5N4 (c); For incomplete derivatization, MALDI-MS detected (a), (c), and p-Toluidine labeled two sialic acids S2H5N4 (b); When completely labeled, only (b) was detected by MALDI-MS.