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Here, we develop TEO-GalNAc (MS Tag-free Enrichment of O-GalNAc), a chemoenzymatic strategy that integrates ST6GalNAc1-catalyzed labeling with a ketone-modified CMP-sialic acid donor, reversible oxime capture, and mild acid-catalyzed tag removal prior to MS analysis. Using TEO-GalNAc, we identified 489 unique Tn\/T glycopeptides from human serum and 1,068 unique Tn\/T glycopeptides from Jurkat cell lysates, demonstrating the applicability of the workflow to complex biological samples. Importantly, this approach enables relative assessment of GalNAc-associated sialylation occupancy by comparing results with or without preservation of endogenous sialic acids prior to enzymatic tagging. Using this analytical framework, we observed differential labeling patterns between nonmetastatic MCF-7 and metastatic MDA-MB-231 cells, including distinct signals associated with several glycoproteins such as MUC1, GLU2B, MESD, and SEL1L. By enabling tag-removable chemoenzymatic enrichment and MS-compatible analysis of Tn\/T-associated glycopeptides, TEO-GalNAc provides a complementary analytical strategy for studying truncated O-glycosylation in complex biological samples.<\/jats:p>","DOI":"10.1021\/acschembio.6c00467","type":"journal-article","created":{"date-parts":[[2026,7,22]],"date-time":"2026-07-22T16:12:56Z","timestamp":1784736776000},"page":"2021-2031","source":"Crossref","is-referenced-by-count":0,"title":["TEO-GalNAc: MS Tag-Free Chemoenzymatic Enrichment\nand Relative Assessment of Tn\/T Antigen Sialylation Occupancy via\nKetone-Oxime Chemistry"],"prefix":"10.1021","volume":"21","author":[{"given":"Li","family":"Liu","sequence":"first","affiliation":[{"name":"State Key Laboratory of Medical Proteomics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences , ,","place":["Dalian, China, 116023"]},{"name":"University of Chinese Academy of Sciences , ,","place":["Beijing, China, 101408"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6998-0612","authenticated-orcid":true,"given":"Yinping","family":"Tian","sequence":"additional","affiliation":[{"name":"Carbohydrate-Based Drug Research Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , ,","place":["Shanghai, China, 201203"]},{"name":"University of Chinese Academy of Sciences , ,","place":["Beijing, China, 101408"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhuo","family":"Zhang","sequence":"additional","affiliation":[{"name":"Dalian University of Technology , , , ,","place":["Dalian, Liaoning, China, 116024"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xuyang","family":"Yue","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Medical Proteomics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences , ,","place":["Dalian, China, 116023"]},{"name":"University of Chinese Academy of Sciences , ,","place":["Beijing, China, 101408"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9187-7999","authenticated-orcid":true,"given":"Liuqing","family":"Wen","sequence":"additional","affiliation":[{"name":"Carbohydrate-Based Drug Research Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , ,","place":["Shanghai, China, 201203"]},{"name":"University of Chinese Academy of Sciences , ,","place":["Beijing, China, 101408"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5872-9326","authenticated-orcid":true,"given":"Mingliang","family":"Ye","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Medical Proteomics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences , ,","place":["Dalian, China, 116023"]},{"name":"University of Chinese Academy of Sciences , ,","place":["Beijing, China, 101408"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7508-0872","authenticated-orcid":true,"given":"Hongqiang","family":"Qin","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Medical Proteomics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences , ,","place":["Dalian, China, 116023"]},{"name":"Dalian University of Technology , , , ,","place":["Dalian, Liaoning, China, 116024"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,7,22]]},"reference":[{"issue":"6","key":"2026082208554012300_cit1","doi-asserted-by":"publisher","first-page":"736","DOI":"10.1093\/glycob\/cwr182","article-title":"Control of mucin-type O-glycosylation: A classification\nof the polypeptide GalNAc-transferase gene family","volume":"22","author":"Bennett","year":"2012","journal-title":"Glycobiology"},{"issue":"6","key":"2026082208554012300_cit2","doi-asserted-by":"publisher","first-page":"599","DOI":"10.1038\/sj.embor.7400705","article-title":"Mucin-type-glycans\nin human colon and breast cancer: glycodynamics and functions","volume":"7","author":"Brockhausen","year":"2006","journal-title":"EMBO Rep."},{"issue":"3","key":"2026082208554012300_cit3","doi-asserted-by":"publisher","DOI":"10.3390\/ijms17030275","article-title":"The Role of\nSialyl-Tn in Cancer","volume":"17","author":"Munkley","year":"2016","journal-title":"Int. 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Biol."},{"issue":"30","key":"2026082208554012300_cit17","doi-asserted-by":"publisher","first-page":"20539","DOI":"10.1021\/jacs.4c03632","article-title":"A Versatile\nOne-Step Enzymatic Strategy for Efficient Imaging and Mapping of Tumor-Associated\nTn Antigen","volume":"146","author":"Li","year":"2024","journal-title":"J. Am. Chem. Soc."},{"issue":"10\u201311","key":"2026082208554012300_cit18","doi-asserted-by":"publisher","DOI":"10.1002\/ijch.202300081","article-title":"Chemoenzymatic Tagging of Tn\/TF\/STF\nAntigens in Living Systems","volume":"63","author":"Yang","year":"2023","journal-title":"Isr. J. Chem."},{"issue":"4","key":"2026082208554012300_cit19","doi-asserted-by":"publisher","first-page":"451","DOI":"10.1021\/acscentsci.7b00573","article-title":"A One-Step Chemoenzymatic Labeling Strategy for Probing\nSialylated Thomsen-Friedenreich Antigen","volume":"4","author":"Wen","year":"2018","journal-title":"ACS\nCentral Sci."},{"issue":"14","key":"2026082208554012300_cit20","doi-asserted-by":"publisher","first-page":"7833","DOI":"10.1021\/acs.analchem.4c06400","article-title":"One-Step\nLabeling Strategy for the\nProfiling of Multiple Types of Protein Glycosylation","volume":"97","author":"Tian","year":"2025","journal-title":"Anal. 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Chem."},{"issue":"25","key":"2026082208554012300_cit24","doi-asserted-by":"publisher","first-page":"7107","DOI":"10.1002\/anie.201702191","article-title":"Specific\nIdentification of Glycoproteins\nBearing the Tn Antigen in Human Cells","volume":"56","author":"Zheng","year":"2017","journal-title":"Angew.\nChem."},{"issue":"36","key":"2026082208554012300_cit25","doi-asserted-by":"publisher","first-page":"11575","DOI":"10.1021\/jacs.6b04049","article-title":"One-Step Selective\nExoenzymatic Labeling (SEEL) Strategy for the Biotinylation and Identification\nof Glycoproteins of Living Cells","volume":"138","author":"Sun","year":"2016","journal-title":"J. Am. Chem.\nSoc."},{"issue":"49","key":"2026082208554012300_cit26","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202206802","article-title":"A Sensitive and Reversible Labeling\nStrategy Enables Global Mapping of the Core-Fucosylated Glycoproteome\non Cell Surfaces","volume":"61","author":"Tian","year":"2022","journal-title":"Angew. Chem."},{"issue":"29","key":"2026082208554012300_cit27","doi-asserted-by":"publisher","first-page":"15879","DOI":"10.1021\/jacs.3c02976","article-title":"\u2033Two\nBirds One Stone\u2033 Strategy for the Site-Specific Analysis of\nCore Fucosylation and O-GlcNAcylation","volume":"145","author":"Luo","year":"2023","journal-title":"J. Am.\nChem. Soc."},{"issue":"49","key":"2026082208554012300_cit28","doi-asserted-by":"publisher","first-page":"16618","DOI":"10.1021\/acs.analchem.1c04031","article-title":"Highly Efficient Enrichment of O-GlcNAc\nGlycopeptides Based on Chemical Oxidation and Reversible Hydrazide\nChemistry","volume":"93","author":"Chen","year":"2021","journal-title":"Anal. 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Chem."},{"issue":"11","key":"2026082208554012300_cit37","doi-asserted-by":"publisher","DOI":"10.15252\/msb.20188486","article-title":"Mapping the\nO-glycoproteome using site-specific extraction of O-linked glycopeptides\n(EXoO)","volume":"14","author":"Yang","year":"2018","journal-title":"Mol. Syst. Biol."},{"issue":"5","key":"2026082208554012300_cit38","doi-asserted-by":"publisher","first-page":"229","DOI":"10.1038\/s41570-020-0174-3","article-title":"Glycomics studies using\nsialic acid derivatization and mass spectrometry","volume":"4","author":"De Haan","year":"2020","journal-title":"Nat. Rev. Chem."},{"issue":"45","key":"2026082208554012300_cit39","doi-asserted-by":"publisher","first-page":"22706","DOI":"10.1039\/c3ra42969e","article-title":"Structural\nanalysis of glycoprotein sialylation -part II: LC-MS based detection","volume":"3","author":"Palmisano","year":"2013","journal-title":"Rsc Adv."},{"issue":"29","key":"2026082208554012300_cit40","doi-asserted-by":"publisher","first-page":"6271","DOI":"10.1039\/C8SC01875H","article-title":"Membrane glycomics\nreveal heterogeneity and quantitative\ndistribution of cell surface sialylation","volume":"9","author":"Park","year":"2018","journal-title":"Chem.\nSci."},{"issue":"23","key":"2026082208554012300_cit41","doi-asserted-by":"publisher","DOI":"10.1111\/jcmm.70279","article-title":"Targeting Tn Antigen Suppresses Aberrant O-Glycosylation-Elicited\nMetastasis in Breast Cancer","volume":"28","author":"Du","year":"2024","journal-title":"J. Cell Mol. Med."},{"issue":"3","key":"2026082208554012300_cit42","doi-asserted-by":"publisher","DOI":"10.1186\/bcr2577","article-title":"Tumour-associated\ncarbohydrate antigens in breast cancer","volume":"12","author":"Cazet","year":"2010","journal-title":"Breast\nCancer Res."},{"issue":"14","key":"2026082208554012300_cit43","doi-asserted-by":"publisher","DOI":"10.3390\/cancers15143536","article-title":"Aberrant Glycosylation\nas Immune Therapeutic Targets for Solid Tumors","volume":"15","author":"Matsumoto","year":"2023","journal-title":"Cancers"}],"container-title":["ACS Chemical Biology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acschembio.6c00467","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acbcct\/article-pdf\/21\/8\/2021\/66125377\/acschembio.6c00467.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acbcct\/article-pdf\/21\/8\/2021\/66125377\/acschembio.6c00467.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,22]],"date-time":"2026-08-22T12:55:51Z","timestamp":1787403351000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acbcct\/article\/21\/8\/2021\/5226844\/TEO-GalNAc-MS-Tag-Free-Chemoenzymatic-Enrichment"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,7,22]]},"references-count":43,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2026,7,22]]},"published-print":{"date-parts":[[2026,8,21]]}},"URL":"https:\/\/doi.org\/10.1021\/acschembio.6c00467","relation":{},"ISSN":["1554-8929","1554-8937"],"issn-type":[{"value":"1554-8929","type":"print"},{"value":"1554-8937","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,7,22]]}}}