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Despite their significant biological relevance, the systematic synthesis of 3FL-HMOs has remained challenging due to their structural diversity and complexity, which has hindered comprehensive functional studies. Herein, we report a highly efficient enzymatic modular assembly strategy for the collective synthesis of 32 3FL-HMOs, encompassing 5 core backbones and 11 distinct terminal epitopes. Notably, this approach employs a sialic acid-assisted, site-specific \u03b11,3-fucosylation strategy to enable the precise installation of diverse fucosylation patterns on oligosaccharide scaffolds.<\/jats:p>","DOI":"10.1021\/acs.jafc.6c10253","type":"journal-article","created":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T19:01:58Z","timestamp":1790017318000},"page":"30241-30249","source":"Crossref","is-referenced-by-count":0,"title":["Diversity-Oriented\nEnzymatic Synthesis of Human Milk\nOligosaccharides Bearing a 3-Fucosyllactose Core"],"prefix":"10.1021","volume":"74","author":[{"given":"Yun","family":"Li","sequence":"first","affiliation":[{"name":"Ocean University of China , , , ,","place":["Qingdao, Shandong, China, 266003"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hui","family":"Xia","sequence":"additional","affiliation":[{"name":"Qingdao University of Science and Technology , , ,","place":["Qingdao, China, 266042"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kan","family":"Zhong","sequence":"additional","affiliation":[{"name":"Ocean University of China , , , ,","place":["Qingdao, Shandong, China, 266003"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Haoxuan","family":"Zhong","sequence":"additional","affiliation":[{"name":"Ocean University of China , , , ,","place":["Qingdao, Shandong, China, 266003"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Huashuai","family":"Ding","sequence":"additional","affiliation":[{"name":"Ocean University of China , , , ,","place":["Qingdao, Shandong, China, 266003"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xihuan","family":"Hu","sequence":"additional","affiliation":[{"name":"Ocean University of China , , , ,","place":["Qingdao, Shandong, China, 266003"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhifei","family":"Hu","sequence":"additional","affiliation":[{"name":"Ocean University of China , , , ,","place":["Qingdao, Shandong, China, 266003"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4736-3143","authenticated-orcid":true,"given":"Hongzhi","family":"Cao","sequence":"additional","affiliation":[{"name":"Ocean University of China , , , ,","place":["Qingdao, Shandong, China, 266003"]},{"name":"Ocean University of China , , ,","place":["Sanya, China, 572025"]},{"name":"Qingdao Marine Science and Technology Center , , , ,","place":["Qingdao, Shandong, China, 266237"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,21]]},"reference":[{"key":"2026093009080587100_cit1","doi-asserted-by":"publisher","first-page":"113","DOI":"10.1016\/bs.accb.2015.08.002","article-title":"Human milk\noligosaccharides (HMOs): structure, function, and enzyme-catalyzed\nsynthesis","volume":"72","author":"Chen","year":"2015","journal-title":"Adv. Carbohydr. Chem. Biochem."},{"key":"2026093009080587100_cit2","doi-asserted-by":"publisher","first-page":"89","DOI":"10.1111\/j.1651-2227.1999.tb01307.x","article-title":"Oligosaccharides\nin human milk during different phases\nof lactation","volume":"88","author":"Coppa","year":"2007","journal-title":"Acta Paediatr Suppl."},{"key":"2026093009080587100_cit3","doi-asserted-by":"publisher","first-page":"5563","DOI":"10.1021\/acs.analchem.4c06081","article-title":"Robust and high-resolution\nall-ion fragmentation LC-ESI-IM-MS analysis\nfor in-depth characterization or profiling of up to 200 human milk\noligosaccharides","volume":"97","author":"Gonsalves","year":"2025","journal-title":"Anal. Chem."},{"key":"2026093009080587100_cit4","doi-asserted-by":"publisher","first-page":"514","DOI":"10.1038\/s41929-019-0281-z","article-title":"Reprogramming the enzymatic\nassembly line for site-specific fucosylation","volume":"2","author":"Ye","year":"2019","journal-title":"Nat. Catal."},{"key":"2026093009080587100_cit5","doi-asserted-by":"publisher","first-page":"1147","DOI":"10.1093\/glycob\/cws074","article-title":"Human milk\noligosaccharides: every baby needs a sugar mama","volume":"22","author":"Bode","year":"2012","journal-title":"Glycobiology"},{"key":"2026093009080587100_cit6","doi-asserted-by":"publisher","first-page":"15908","DOI":"10.1021\/acs.jafc.3c04412","article-title":"Human milk\noligosaccharides: a critical review on structure, preparation,\ntheir potential as a food bioactive component, and future perspectives","volume":"71","author":"Zhu","year":"2023","journal-title":"J. Agric. Food Chem."},{"key":"2026093009080587100_cit7","doi-asserted-by":"publisher","first-page":"2570","DOI":"10.1038\/s41564-024-01804-9","article-title":"Primary succession of\nBifidobacteria drives pathogen resistance in neonatal microbiota assembly","volume":"9","author":"Shao","year":"2024","journal-title":"Nat. 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Food Chem."},{"key":"2026093009080587100_cit18","doi-asserted-by":"publisher","first-page":"104203","DOI":"10.1016\/j.tifs.2023.104203","article-title":"Advances and challenges\nfor obtaining human milk oligosaccharides: extraction from natural\nsources and synthesis by intentional design","volume":"141","author":"Gan","year":"2023","journal-title":"Trends Food Sci. Technol."},{"key":"2026093009080587100_cit19","doi-asserted-by":"publisher","first-page":"13390","DOI":"10.1021\/acscatal.4c03373","article-title":"Regioselective enzymatic\ngalactosylation enabled divergent synthesis of asymmetrical biantennary\nhuman milk oligosaccharides","volume":"14","author":"Xia","year":"2024","journal-title":"ACS Catal."},{"key":"2026093009080587100_cit20","doi-asserted-by":"publisher","first-page":"108029","DOI":"10.1016\/j.carres.2020.108029","article-title":"Enzymatic transfucosylation for synthesis\nof human\nmilk oligosaccharides","volume":"493","author":"Zeuner","year":"2020","journal-title":"Carbohydr. Res."},{"key":"2026093009080587100_cit21","doi-asserted-by":"publisher","first-page":"12390","DOI":"10.1021\/acs.jafc.3c02895","article-title":"An overview\nof sugar nucleotide-dependent glycosyltransferases for human milk\noligosaccharide synthesis","volume":"71","author":"Zhao","year":"2023","journal-title":"J. Agric. Food Chem."},{"key":"2026093009080587100_cit22","doi-asserted-by":"publisher","first-page":"1479","DOI":"10.1002\/cjoc.70014","article-title":"Ketodeoxynonulosonic acid hydroxylase\n(Kdnase) assisted site-specific enzymatic \u03b12,6-sialylation","volume":"43","author":"Zhou","year":"2025","journal-title":"Chin. J. Chem."},{"key":"2026093009080587100_cit23","doi-asserted-by":"publisher","first-page":"21283","DOI":"10.1021\/acs.jafc.5c08264","article-title":"Glycosyltransferases for human milk\noligosaccharide synthesis: from\nstructural understanding to engineering","volume":"73","author":"Luo","year":"2025","journal-title":"J.\nAgric. Food Chem."},{"key":"2026093009080587100_cit24","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1016\/j.carres.2019.05.007","article-title":"Biochemical characterization of Helicobacter pylori \u03b11-3-fucosyltransferase and its application in the synthesis\nof fucosylated human milk oligosaccharides","volume":"480","author":"Bai","year":"2019","journal-title":"Carbohydr. Res."},{"key":"2026093009080587100_cit25","doi-asserted-by":"publisher","first-page":"822","DOI":"10.1021\/jacsau.4c01094","article-title":"EASyMap-guided\nstepwise one-pot multienzyme (StOPMe) synthesis and multiplex assays\nidentify functional tetraose-core-human milk oligosaccharides","volume":"5","author":"Bai","year":"2025","journal-title":"JACS Au"},{"key":"2026093009080587100_cit26","doi-asserted-by":"publisher","first-page":"10721","DOI":"10.1021\/acscatal.9b03990","article-title":"A bacterial\n\u03b21-3-galactosyltransferase enables\nmultigram-scale synthesis of human milk lacto-N-tetraose\n(LNT) and its fucosides","volume":"9","author":"McArthur","year":"2019","journal-title":"ACS Catal."},{"key":"2026093009080587100_cit27","doi-asserted-by":"publisher","first-page":"7132","DOI":"10.1039\/C4CC02222J","article-title":"A multifunctional\nanomeric linker for the chemoenzymatic synthesis of complex oligosaccharides","volume":"50","author":"Prudden","year":"2014","journal-title":"Chem. Commun."},{"key":"2026093009080587100_cit28","doi-asserted-by":"publisher","first-page":"6954","DOI":"10.1073\/pnas.1701785114","article-title":"Synthesis of asymmetrical\nmultiantennary human milk oligosaccharides","volume":"114","author":"Prudden","year":"2017","journal-title":"Proc. Natl. Acad. Sci. U. S. A."},{"key":"2026093009080587100_cit29","doi-asserted-by":"publisher","first-page":"10712","DOI":"10.1021\/acscatal.9b03752","article-title":"Exploring the synthetic\napplication of Helicobacter pylori \u03b11,3\/4-fucosyltransferase\nFucTIII toward the syntheses of fucosylated human milk glycans and\nLewis antigens","volume":"9","author":"Tsai","year":"2019","journal-title":"ACS Catal."},{"key":"2026093009080587100_cit30","doi-asserted-by":"publisher","first-page":"11012","DOI":"10.1039\/c7cc05403c","article-title":"Helicobacter pylori \u03b11-3\/4-fucosyltransferase\n(Hp3\/4FT)-catalyzed\none-pot multienzyme (OPME) synthesis of Lewis antigens and human milk\nfucosides","volume":"53","author":"Yu","year":"2017","journal-title":"Chem. Commun."},{"key":"2026093009080587100_cit31","doi-asserted-by":"publisher","first-page":"169","DOI":"10.1093\/glycob\/cws138","article-title":"The principal fucosylated\noligosaccharides of human milk exhibit prebiotic properties on cultured\ninfant microbiota","volume":"23","author":"Yu","year":"2013","journal-title":"Glycobiology"},{"key":"2026093009080587100_cit32","doi-asserted-by":"publisher","first-page":"636","DOI":"10.1021\/acs.accounts.3c00754","article-title":"Chemical evolution of enzyme-catalyzed glycosylation","volume":"57","author":"Liu","year":"2024","journal-title":"Acc. Chem. Res."},{"key":"2026093009080587100_cit33","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202418929","article-title":"Sugar auxiliary\ngroup assisted diversity-oriented enzymatic\nmodular synthesis of 0-series ganglioside glycans","volume":"64","author":"Ye","year":"2025","journal-title":"Angew. Chem. Int. Ed."},{"key":"2026093009080587100_cit34","doi-asserted-by":"publisher","first-page":"4207","DOI":"10.1073\/pnas.0812432106","article-title":"Remodeling\nbacterial polysaccharides by metabolic pathway engineering","volume":"106","author":"Yi","year":"2009","journal-title":"Proc. Natl. Acad. Sci. U. S. A."},{"key":"2026093009080587100_cit35","doi-asserted-by":"publisher","first-page":"1666","DOI":"10.1002\/bit.25944","article-title":"Solubilization\nand iterative saturation mutagenesis of \u03b11,3-fucosyltransferase\nfrom Helicobacter pylori to enhance its catalytic\nefficiency","volume":"113","author":"Choi","year":"2016","journal-title":"Biotechnol. Bioeng."},{"key":"2026093009080587100_cit36","doi-asserted-by":"publisher","first-page":"6427","DOI":"10.1016\/j.bmc.2004.09.030","article-title":"Chemoenzymatic synthesis of CMP-sialic\nacid derivatives by a one-pot two-enzyme system: comparison of substrate\nflexibility of three microbial CMP-sialic acid synthetases","volume":"12","author":"Yu","year":"2004","journal-title":"Bioorg. Med. Chem."},{"key":"2026093009080587100_cit37","doi-asserted-by":"publisher","first-page":"1232","DOI":"10.1021\/cb300125k","article-title":"A sialyltransferase\nmutant with decreased donor hydrolysis and reduced sialidase activities\nfor directly sialylating Lewisx","volume":"7","author":"Sugiarto","year":"2012","journal-title":"ACS Chem. Biol."},{"key":"2026093009080587100_cit38","doi-asserted-by":"publisher","first-page":"977","DOI":"10.1007\/s00253-011-3676-6","article-title":"PmST3 from Pasteurella\nmultocida encoded by Pm1174 gene is a monofunctional \u03b12-3-sialyltransferase","volume":"94","author":"Thon","year":"2012","journal-title":"Appl. Microbiol. Biotechnol."},{"issue":"12","key":"2026093009080587100_cit39","doi-asserted-by":"publisher","first-page":"8140","DOI":"10.1021\/acscatal.6b02755","article-title":"Diversity-Oriented Enzymatic Modular\nAssembly of ABO Histo-blood Group Antigens","volume":"6","author":"Ye","year":"2016","journal-title":"ACS Catal."},{"key":"2026093009080587100_cit40","doi-asserted-by":"publisher","first-page":"1321","DOI":"10.1007\/s10529-012-0910-y","article-title":"NahK\/GlmU\nfusion enzyme:\ncharacterization and one-step enzymatic synthesis of UDP-N-acetylglucosamine","volume":"34","author":"Zhai","year":"2012","journal-title":"Biotechnol. 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Commun."},{"key":"2026093009080587100_cit44","doi-asserted-by":"publisher","first-page":"323","DOI":"10.1111\/j.1432-1033.1995.323_c.x","article-title":"Expression\nof a recombinant human glycosyltransferase from a synthetic gene and\nits utilization for synthesis of the human blood group B trisaccharide","volume":"234","author":"Seto","year":"1995","journal-title":"Eur. J. Biochem."},{"key":"2026093009080587100_cit45","doi-asserted-by":"publisher","first-page":"6635","DOI":"10.1021\/ja9808898","article-title":"Highly\nefficient chemoenzymatic synthesis of \u03b1-galactosyl epitopes\nwith a recombinant \u03b11,3-galactosyltransferase","volume":"120","author":"Fang","year":"1998","journal-title":"J. Am. Chem. Soc."},{"key":"2026093009080587100_cit46","doi-asserted-by":"publisher","first-page":"1696","DOI":"10.1016\/j.bmc.2016.02.043","article-title":"Donor substrate\npromiscuity of bacterial \u03b21-3-N-acetylglucosaminyltransferases\nand acceptor substrate flexibility of \u03b21-4-galactosyltransferases","volume":"24","author":"Li","year":"2016","journal-title":"Bioorg. Med. Chem."},{"key":"2026093009080587100_cit47","doi-asserted-by":"publisher","first-page":"6066","DOI":"10.1039\/c0cc01381a","article-title":"Highly efficient\nchemoenzymatic synthesis of \u03b21-4-linked galactosides with promiscuous\nbacterial \u03b21-4-galactosyltransferases","volume":"46","author":"Lau","year":"2010","journal-title":"Chem. Commun."},{"key":"2026093009080587100_cit48","doi-asserted-by":"publisher","first-page":"13305","DOI":"10.1021\/acs.orglett.5c04338","article-title":"Diversity-oriented\nenzymatic modular\nsynthesis of N-glycans bearing LacdiNAc-related epitopes","volume":"27","author":"Yin","year":"2025","journal-title":"Org. Lett."},{"key":"2026093009080587100_cit49","doi-asserted-by":"publisher","first-page":"4313","DOI":"10.1016\/j.tet.2005.02.023","article-title":"A new one-pot synthesis\nof \u03b1-Gal epitope derivatives involved in the hyperacute rejection\nresponse in xenotransplantation","volume":"61","author":"Wang","year":"2005","journal-title":"Tetrahedron"}],"container-title":["Journal of Agricultural\nand Food Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.jafc.6c10253","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jafcau\/article-pdf\/74\/38\/30241\/68584512\/acs.jafc.6c10253.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jafcau\/article-pdf\/74\/38\/30241\/68584512\/acs.jafc.6c10253.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T13:49:38Z","timestamp":1790776178000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jafcau\/article\/74\/38\/30241\/5434506\/Diversity-Oriented-Enzymatic-Synthesis-of-Human"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,21]]},"references-count":49,"journal-issue":{"issue":"38","published-online":{"date-parts":[[2026,9,21]]},"published-print":{"date-parts":[[2026,9,30]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.jafc.6c10253","relation":{},"ISSN":["0021-8561","1520-5118"],"issn-type":[{"value":"0021-8561","type":"print"},{"value":"1520-5118","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,21]]}}}