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Here, we report a general and bioorthogonal strategy for RNA labeling by leveraging enzyme\u2010installable allyl modifications as dienophile handles for tetrazine cycloaddition. Guided by frontier\u2010orbital analysis, we identified 1,2,4,5\u2010tetrazine\u20103,6\u2010dicarboxylate (Tz\n                    <jats:bold>5<\/jats:bold>\n                    ) as an activated electron\u2010deficient diene capable of engaging electronically unactivated allyl handles in IEDDA reactions under nonaqueous conditions. Tz\n                    <jats:bold>5<\/jats:bold>\n                    reacts efficiently with both N6\u2010allyladenosine (a\n                    <jats:sup>6<\/jats:sup>\n                    A) and 2\u2032\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010allyladenosine (A\n                    <jats:sub>a<\/jats:sub>\n                    ), forming stable cycloaddition adducts in nucleosides and within RNA oligonucleotides without perturbing canonical bases or phosphate linkages. The IEDDA labeling proceeds with high selectivity, and enzymatic digestion confirms site\u2010specific conjugation exclusively at the allyl\u2010modified nucleosides. These findings expand the scope of IEDDA chemistry to unstrained, electron\u2010rich terminal alkenes in RNA and establish a\n                    <jats:sup>6<\/jats:sup>\n                    A and A\n                    <jats:sub>a<\/jats:sub>\n                    as versatile, orthogonal handles for tetrazine\u2010mediated labeling. This article offers a broadly applicable platform for selective RNA functionalization and provides new opportunities for probing, imaging, and manipulating RNA in complex biological environments.\n                  <\/jats:p>","DOI":"10.1002\/cbic.70229","type":"journal-article","created":{"date-parts":[[2026,3,8]],"date-time":"2026-03-08T14:20:37Z","timestamp":1772979637000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Selective RNA Labeling Using Tetrazine\u2010Based IEDDA Reactions With Allyl Adenosine Modifications"],"prefix":"10.1002","volume":"27","author":[{"given":"Feng","family":"Ge","sequence":"first","affiliation":[{"name":"Beijing National Laboratory for Molecular Sciences (BNLMS) CAS Key Laboratory of Molecular Recognition and Function CAS Research\/Education Center for Excellence in Molecular Sciences Institute of Chemistry Chinese Academy of Sciences  Beijing China"},{"name":"University of Chinese Academy of Sciences  Beijing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0818-3900","authenticated-orcid":false,"given":"Li","family":"Liu","sequence":"additional","affiliation":[{"name":"Beijing National Laboratory for Molecular Sciences (BNLMS) CAS Key Laboratory of Molecular Recognition and Function CAS Research\/Education Center for Excellence in Molecular Sciences Institute of Chemistry Chinese Academy of Sciences  Beijing China"},{"name":"University of Chinese Academy of Sciences  Beijing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7427-2939","authenticated-orcid":false,"given":"Liang","family":"Cheng","sequence":"additional","affiliation":[{"name":"Beijing National Laboratory for Molecular Sciences (BNLMS) CAS Key Laboratory of Molecular Recognition and Function CAS Research\/Education Center for Excellence in Molecular Sciences Institute of Chemistry Chinese 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