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While multivalent presentation of carbohydrates is widely recognized as crucial for high\u2010affinity target binding (the glycoside cluster effect), most existing methods focus on installing one glycosidic bond and lack robust strategies for attaching multiple carbohydrate units to a functional group. Here we report a mild, operationally simple protocol for the direct, stereoselective bis\u2010\n                    <jats:italic>S<\/jats:italic>\n                    \u2010glycosylation of dialkyl disulfide bonds in an open\u2010flask aqueous solution. This transformation installs two unprotected glycosyl units onto disulfide bonds, affording fully unprotected\n                    <jats:italic>S<\/jats:italic>\n                    \u2010linked glycopeptides. The reaction employs bench\u2010stable, readily accessible glycosyl sulfinates as donors and\n                    <jats:italic>tert<\/jats:italic>\n                    \u2010butyl hydroperoxide (\n                    <jats:italic>t<\/jats:italic>\n                    BuOOH) as oxidant, forging cysteine\u2010glycosyl linkages via a radical pathway. Mixed disulfides derived from thiols partook in this reaction as well, allowing installation of one sugar unit onto peptide backbones. We applied this method to synthesize glycosylated peptides with liver\u2010targeting capabilities and to generate sugar\u2010linked affibody\u2010radionuclide conjugates. DFT calculations informed the reaction design and rationalized the observed selectivity of this transformation.\n                  <\/jats:p>","DOI":"10.1002\/anie.7774464","type":"journal-article","created":{"date-parts":[[2026,7,24]],"date-time":"2026-07-24T10:50:04Z","timestamp":1784890204000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Bis\u2010\n                    <i>S<\/i>\n                    \u2010Glycosylation of Disulfides"],"prefix":"10.1002","volume":"65","author":[{"given":"Shiyang","family":"Xu","sequence":"first","affiliation":[{"name":"State Key Laboratory of Biotherapy and Cancer Center, West China Hospital Sichuan University  Chengdu China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fei","family":"Hu","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Biotherapy and Cancer Center, West China Hospital Sichuan University  Chengdu China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shuoyingjie","family":"Wang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Biotherapy and Cancer Center, West China Hospital Sichuan University  Chengdu China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Weichen","family":"Wang","sequence":"additional","affiliation":[{"name":"Department of Nuclear Medicine, West China Hospital Sichuan University  Chengdu China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yinqi","family":"Li","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Biotherapy and Cancer Center, West China Hospital Sichuan University  Chengdu China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7888-211X","authenticated-orcid":false,"given":"Zhiyao","family":"He","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Biotherapy and Cancer Center, West China Hospital Sichuan University  Chengdu China"},{"name":"Key Laboratory of Drug\u2010Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant\u2010Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy Sichuan University  Chengdu China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5191-9004","authenticated-orcid":false,"given":"Rong","family":"Tian","sequence":"additional","affiliation":[{"name":"Department of Nuclear Medicine, West China Hospital Sichuan University  Chengdu China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5073-0269","authenticated-orcid":false,"given":"Xia","family":"Zhang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Biotherapy and Cancer Center, West China Hospital Sichuan University  Chengdu China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9118-5164","authenticated-orcid":false,"given":"Yingwei","family":"Wang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Biotherapy and Cancer Center, West China Hospital Sichuan University  Chengdu China"},{"name":"Department of Nuclear Medicine, West China Hospital Sichuan University  Chengdu China"},{"name":"Tian Fu Jincheng Laboratory  Chengdu China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5114-4413","authenticated-orcid":false,"given":"Dawen","family":"Niu","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Biotherapy and Cancer Center, West China Hospital Sichuan University  Chengdu China"},{"name":"Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing Key Laboratory of Carbohydrate Intelligent Manufacture and Functional Applications, College of Chemistry and Molecular Engineering Peking University  Beijing China"},{"name":"Peking\u2010Tsinghua Center for Life Science, Academy for Advanced Interdisciplinary Studies Peking University  Beijing China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,7,24]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1059820"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1093\/glycob\/12.4.43R"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrm3383"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527621644"},{"key":"e_1_2_8_6_1","volume-title":"Modern Synthetic Methods in Carbohydrate Chemistry: From Monosaccharides to Comples Glycocojugates","author":"Werz D. 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