{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,28]],"date-time":"2026-10-28T03:12:22Z","timestamp":1793157142263,"version":"4.5.0"},"reference-count":27,"publisher":"American Chemical Society (ACS)","issue":"7","license":[{"start":{"date-parts":[[2026,6,17]],"date-time":"2026-06-17T00:00:00Z","timestamp":1781654400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/100017380","name":"Science and Technology Foundation of Shenzhen City","doi-asserted-by":"publisher","award":["JCYJ20241202124932044"],"award-info":[{"award-number":["JCYJ20241202124932044"]}],"id":[{"id":"10.13039\/100017380","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22577167"],"award-info":[{"award-number":["22577167"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003453","name":"Natural Science Foundation of Guangdong Province","doi-asserted-by":"publisher","award":["2024A1515010015"],"award-info":[{"award-number":["2024A1515010015"]}],"id":[{"id":"10.13039\/501100003453","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100012245","name":"Science and Technology Planning Project of Guangdong Province","doi-asserted-by":"publisher","award":["2024B1111160007"],"award-info":[{"award-number":["2024B1111160007"]}],"id":[{"id":"10.13039\/501100012245","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,7,27]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Despite the biological significance of stereodefined phenolic O-glycosides, their efficient synthesis remains challenging. Here, we report the stereoselective O-furanosylation of phenols toward bench-stable glycosyl fluorides by cooperative activation of a Lewis acid and transition-metal complex, proceeding in high yields at room temperature. The novel glycosylation strategy is demonstrated to be effective for a wide substrate scope of acceptors, including small molecules, natural products, and commercial drugs. Mechanistic studies, supported by TEMPO-trapping and DFT simulations, established a radical-mediated pathway for this glycosylation. To demonstrate the utility of this strategy for bioactive molecule diversification, we focused on phenolic compounds with known anti-inflammatory properties (e.g., sesamol). Their ribofuranose conjugates were synthesized and evaluated, leading to the discovery that glycosylation could potentiate the parent compounds\u2019 ability to inhibit IL-6 production in LPS-stimulated macrophages, thereby demonstrating the potential of this glycosylation strategy to improve the pharmacological profiles of bioactive phenols.<\/jats:p>","DOI":"10.1021\/jacsau.6c00351","type":"journal-article","created":{"date-parts":[[2026,6,17]],"date-time":"2026-06-17T12:44:54Z","timestamp":1781700294000},"page":"3768-3777","source":"Crossref","is-referenced-by-count":1,"title":["Stereoselective\n                    <i>O<\/i>\n                    -Furanosylation\nof Phenols by Cooperative Effect of Lewis Acid and Nickel Complex"],"prefix":"10.1021","volume":"6","author":[{"given":"Sixian","family":"Fang","sequence":"first","affiliation":[{"name":"Shenzhen Campus of Sun Yat-sen University , , ,","place":["Shenzhen, China, 518107"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaoyu","family":"Li","sequence":"additional","affiliation":[{"name":"Shenzhen Campus of Sun Yat-sen University , , ,","place":["Shenzhen, China, 518107"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aoxin","family":"Guo","sequence":"additional","affiliation":[{"name":"Nanyang Technological University , , ,","place":["Singapore, Singapore, 637371"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cai","family":"Huang","sequence":"additional","affiliation":[{"name":"Shenzhen Campus of Sun Yat-sen University , , ,","place":["Shenzhen, China, 518107"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5394-8167","authenticated-orcid":true,"given":"Hui","family":"Cai","sequence":"additional","affiliation":[{"name":"Shenzhen Campus of Sun Yat-sen University , , ,","place":["Shenzhen, China, 518107"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9808-6890","authenticated-orcid":true,"given":"Xiaozhou","family":"Luo","sequence":"additional","affiliation":[{"name":"Shenzhen Institute of Synthetic Biology, Shenzhen Institutes of Advanced Technology, Chinese Academy of Sciences , , ,","place":["Shenzhen, China, 518055"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8327-6664","authenticated-orcid":true,"given":"Xue-Wei","family":"Liu","sequence":"additional","affiliation":[{"name":"Nanyang Technological University , , ,","place":["Singapore, Singapore, 637371"]},{"name":"Ocean University of China , , ,","place":["Qingdao, China, 266003"]},{"name":"Qingdao Marine Science and Technology Center , , ,","place":["Qingdao, China, 266237"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0211-7101","authenticated-orcid":true,"given":"Feiqing","family":"Ding","sequence":"additional","affiliation":[{"name":"Shenzhen Campus of Sun Yat-sen University , , ,","place":["Shenzhen, China, 518107"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,6,17]]},"reference":[{"key":"2026072709064589400_cit1","doi-asserted-by":"publisher","first-page":"15603","DOI":"10.1021\/acs.chemrev.1c01032","article-title":"Glycoconjugates: Synthesis, Functional\nStudies, and Therapeutic Developments","volume":"122","author":"Shivatare","year":"2022","journal-title":"Chem.\nRev."},{"key":"2026072709064589400_cit2","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1016\/B978-0-12-802104-0.00008-1","article-title":"Chapter 8 - Glycosides","volume-title":"Pharmacognosy","author":"Bartnik","year":"2017"},{"key":"2026072709064589400_cit3","doi-asserted-by":"publisher","first-page":"428","DOI":"10.1038\/nature07201","article-title":"Origin and\nPhysiological Roles of Inflammation","volume":"454","author":"Medzhitov","year":"2008","journal-title":"Nature"},{"key":"2026072709064589400_cit4","doi-asserted-by":"publisher","first-page":"860","DOI":"10.1038\/nature05485","article-title":"Inflammation\nand Metabolic Disorders","volume":"444","author":"Hotamisligil","year":"2006","journal-title":"Nature"},{"key":"2026072709064589400_cit5","doi-asserted-by":"publisher","first-page":"680","DOI":"10.1038\/s41577-021-00603-1","article-title":"Immune-mediated Inflammatory Disease\nTherapeutics:\npast, present and future","volume":"21","author":"McInnes","year":"2021","journal-title":"Nat. Rev. Immunol."},{"key":"2026072709064589400_cit6","doi-asserted-by":"publisher","first-page":"6020","DOI":"10.3390\/nu6126020","article-title":"Resources\nand Biological Activities of Natural Polyphenols","volume":"6","author":"Li","year":"2014","journal-title":"Nutrients"},{"key":"2026072709064589400_cit7","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1155\/2013\/934239","article-title":"Antioxidant Lipid\nLowering and Membrane Stabilization\nEffect of Sesamol Against Doxorubicin-induced Cardiomyopathy in Experimental\nRats","volume":"2013","author":"Chennuru","year":"2013","journal-title":"BioMed Res. Int."},{"key":"2026072709064589400_cit8","first-page":"1874","article-title":"Dietary Flavonoid\nAglycones and their Glycosides: Which Show Better Biological Significance?","volume":"57","author":"Xiao","year":"2017","journal-title":"Crit. Rev. Food Sci. Nutr."},{"key":"2026072709064589400_cit9","doi-asserted-by":"publisher","first-page":"437","DOI":"10.1246\/cl.1989.437","article-title":"Rapid O-Glycosidation of Phenols\nwith Glycosyl Fluoride by Using the Combinational Activator, Cp2HfCl2-AgClO4","volume":"18","author":"Matsumoto","year":"1989","journal-title":"Chem. Lett."},{"key":"2026072709064589400_cit10","doi-asserted-by":"publisher","first-page":"4219","DOI":"10.1021\/ol035705v","article-title":"Efficient\nRoute to 2-Deoxy \u03b2-O-aryl-D-glycosides via Direct\nDisplacement of Glycosyl Iodides","volume":"5","author":"Lam","year":"2003","journal-title":"Org. Lett."},{"key":"2026072709064589400_cit11","doi-asserted-by":"publisher","first-page":"644","DOI":"10.1038\/s41557-018-0041-8","article-title":"Rapid Phenolic O-glycosylation of\nSmall Molecules and Complex Unprotected Peptides in Aqueous Solvent","volume":"10","author":"Wadzinski","year":"2018","journal-title":"Nat. Chem."},{"key":"2026072709064589400_cit12","doi-asserted-by":"publisher","first-page":"928","DOI":"10.1126\/science.adk1111","article-title":"Palladium Catalysis\nEnables Cross-coupling-like S(N)2-glycosylation of Phenols","volume":"382","author":"Deng","year":"2023","journal-title":"Science"},{"key":"2026072709064589400_cit13","doi-asserted-by":"publisher","first-page":"34413","DOI":"10.1021\/jacs.4c10633","article-title":"Cooperative Catalysis\nin Stereoselective O- and N-Glycosylations with Glycosyl Trichloroacetimidates\nMediated by Singly Protonated Phenanthrolinium Salt and Trichloroacetamide","volume":"146","author":"Ghorai","year":"2024","journal-title":"J. Am. Chem. 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Lett."},{"key":"2026072709064589400_cit17","doi-asserted-by":"publisher","first-page":"3626","DOI":"10.1021\/acs.orglett.2c01146","article-title":"GeCl2\u00b7Dioxane-AgBF4 Catalyzed Activation of Glycosyl Fluorides for Glycosylation","volume":"24","author":"Zhu","year":"2022","journal-title":"Org. Lett."},{"key":"2026072709064589400_cit18","doi-asserted-by":"publisher","first-page":"4294","DOI":"10.1021\/jacs.2c13641","article-title":"Supramolecular\nCapsule-Catalyzed\nHighly \u03b2-Selective Furanosylation Independent of the SN1\/SN2 Reaction Pathway","volume":"145","author":"Li","year":"2023","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026072709064589400_cit19","doi-asserted-by":"publisher","first-page":"3430","DOI":"10.1016\/j.checat.2022.10.019","article-title":"Recent Advances in\nTransition-metal-catalyzed Glycosyl Cross-coupling Reactions","volume":"2","author":"Chen","year":"2022","journal-title":"Chem Catal."},{"key":"2026072709064589400_cit20","doi-asserted-by":"publisher","first-page":"10224","DOI":"10.1039\/C8CC05108A","article-title":"Activation of C\u2013F\nbonds \u03b1 to C\u2013C\nmultiple bonds","volume":"54","author":"Hamel","year":"2018","journal-title":"Chem. Commun."},{"key":"2026072709064589400_cit21","doi-asserted-by":"publisher","first-page":"4061","DOI":"10.1021\/jacs.0c00335","article-title":"Stereospecific Furanosylations\nCatalyzed by Bis-thiourea Hydrogen-Bond Donors","volume":"142","author":"Mayfield","year":"2020","journal-title":"J. Am. Chem. 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Lett."},{"key":"2026072709064589400_cit25","doi-asserted-by":"publisher","first-page":"2294","DOI":"10.1021\/acs.orglett.2c00431","article-title":"Electrochemical Synthesis of Glycosyl Fluorides Using\nSulfur(VI) Hexafluoride as the Fluorinating Agent","volume":"24","author":"Kim","year":"2022","journal-title":"Org. Lett."},{"key":"2026072709064589400_cit26","first-page":"249","volume-title":"Essentials of Computational\nChemistry: Theories and Models","author":"Cramer","edition":"2"},{"key":"2026072709064589400_cit27","first-page":"233","volume-title":"Introduction to Computational\nChemistry","author":"Jensen","edition":"3"}],"container-title":["JACS Au"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jacsau.6c00351","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jaaucr\/article-pdf\/6\/7\/3768\/65114962\/jacsau.6c00351.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jaaucr\/article-pdf\/6\/7\/3768\/65114962\/jacsau.6c00351.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,7,27]],"date-time":"2026-07-27T13:15:17Z","timestamp":1785158117000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jaaucr\/article\/6\/7\/3768\/5158586\/Stereoselective-O-Furanosylation-of-Phenols-by"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,6,17]]},"references-count":27,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2026,6,17]]},"published-print":{"date-parts":[[2026,7,27]]}},"URL":"https:\/\/doi.org\/10.1021\/jacsau.6c00351","relation":{},"ISSN":["2691-3704"],"issn-type":[{"value":"2691-3704","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,6,17]]}}}