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Traditional cell\u2010selective labeling strategies mainly regulate the insertion of bioorthogonal tags, while we herein report an alternative approach by manipulating the second stage of the labeling process via a controllable hydrazone\/oxime ligation. Hydrazone\/oxime ligation between hydrazides\/hydroxylamines and aldehydes\/ketones is ideal for biomolecular labeling due to the small size of these reactant groups, which can be easily integrated into various biomacromolecules. We introduced stimuli\u2010responsive protecting groups (photoresponsive ortho\u2010nitrobenzyloxycarbonyl, reactive oxygen species (ROS)\u2010responsive benzyloxycarbonyl boronic acid, and leucine aminopeptidase (LAP)\u2010responsive group) to the amino groups of hydroxylamine and hydrazide, thereby inhibiting their reactivity. Upon exposure to the corresponding stimuli (light irradiation, ROS, or LAP), the protecting groups are cleaved, restoring the reactivity of hydrazides\/hydroxylamines and enabling hydrazone\/oxime ligation. Combined with ketone\u2010based metabolic glycan labeling, this strategy achieves selective labeling of cell surface glycoproteins only in stimuli\u2010rich environments. This stimuli\u2010controlled approach holds significant promise for chemical biology labeling and controllable tumor targeting.<\/jats:p>","DOI":"10.1002\/chem.71462","type":"journal-article","created":{"date-parts":[[2026,7,22]],"date-time":"2026-07-22T19:32:08Z","timestamp":1784748728000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Stimuli\u2010Responsive Hydrazone\/Oxime Ligation for Selective Labeling of Cell Surface Glycoproteins"],"prefix":"10.1002","author":[{"given":"Fenxia","family":"Wu","sequence":"first","affiliation":[{"name":"Department of Orthopedics Surgery The Second Xiangya Hospital Central South University  Changsha Hunan China"},{"name":"Changsha Leyuan Chemical Technology Co., Ltd.  Changsha Hunan China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhenkun","family":"Zhang","sequence":"additional","affiliation":[{"name":"College of Chemistry and Chemical Engineering Hunan Normal University  Changsha Hunan China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yating","family":"Lin","sequence":"additional","affiliation":[{"name":"Department of Orthopedics Surgery The Second Xiangya Hospital Central South University  Changsha Hunan China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yan","family":"Zhang","sequence":"additional","affiliation":[{"name":"College of Chemistry and Chemical Engineering Hunan Normal University  Changsha Hunan China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7109-9197","authenticated-orcid":false,"given":"Guhuan","family":"Liu","sequence":"additional","affiliation":[{"name":"College of Chemistry and Chemical Engineering Hunan Normal University  Changsha Hunan China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7926-5148","authenticated-orcid":false,"given":"Ding","family":"Chen","sequence":"additional","affiliation":[{"name":"Department of Orthopedics Surgery The Second Xiangya Hospital Central South University  Changsha Hunan 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