{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,17]],"date-time":"2026-10-17T21:32:36Z","timestamp":1792272756570,"version":"4.4.0"},"reference-count":30,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2024,4,19]],"date-time":"2024-04-19T00:00:00Z","timestamp":1713484800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Qingdao Marine Science and Technology Center","award":["2022QNLM030003\u20131"],"award-info":[{"award-number":["2022QNLM030003\u20131"]}]},{"name":"Qingdao Marine Science and Technology Center","award":["U21A20297"],"award-info":[{"award-number":["U21A20297"]}]},{"name":"Qingdao Marine Science and Technology Center","award":["ZR2023MH302"],"award-info":[{"award-number":["ZR2023MH302"]}]},{"name":"Qingdao Marine Science and Technology Center","award":["2021ZDSYS22"],"award-info":[{"award-number":["2021ZDSYS22"]}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["2022QNLM030003\u20131"],"award-info":[{"award-number":["2022QNLM030003\u20131"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["U21A20297"],"award-info":[{"award-number":["U21A20297"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["ZR2023MH302"],"award-info":[{"award-number":["ZR2023MH302"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["2021ZDSYS22"],"award-info":[{"award-number":["2021ZDSYS22"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Shandong Provincial Natural Science Foundation","award":["2022QNLM030003\u20131"],"award-info":[{"award-number":["2022QNLM030003\u20131"]}]},{"name":"Shandong Provincial Natural Science Foundation","award":["U21A20297"],"award-info":[{"award-number":["U21A20297"]}]},{"name":"Shandong Provincial Natural Science Foundation","award":["ZR2023MH302"],"award-info":[{"award-number":["ZR2023MH302"]}]},{"name":"Shandong Provincial Natural Science Foundation","award":["2021ZDSYS22"],"award-info":[{"award-number":["2021ZDSYS22"]}]},{"name":"Key R&amp;D Program of Shandong province","award":["2022QNLM030003\u20131"],"award-info":[{"award-number":["2022QNLM030003\u20131"]}]},{"name":"Key R&amp;D Program of Shandong province","award":["U21A20297"],"award-info":[{"award-number":["U21A20297"]}]},{"name":"Key R&amp;D Program of Shandong province","award":["ZR2023MH302"],"award-info":[{"award-number":["ZR2023MH302"]}]},{"name":"Key R&amp;D Program of Shandong province","award":["2021ZDSYS22"],"award-info":[{"award-number":["2021ZDSYS22"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>Fucosylated chondroitin sulfate is a unique glycosaminoglycan isolated from sea cucumbers, with excellent anticoagulant activity. The fucosyl branch in FCS is generally located at the 3-OH of D-glucuronic acid but, recently, a novel structure with \u03b1-L-fucose linked to the 6-OH of N-acetyl-galactosamine has been found. Here, using functionalized monosaccharide building blocks, we prepared novel FCS tetrasaccharides with fucosyl branches both at the 6-OH of GalNAc and 3-OH of GlcA. In the synthesis, the protective group strategy of selective O-sulfation, as well as stereoselective glycosylation, was established, which enabled the efficient synthesis of the specific tetrasaccharide compounds. This research enriches knowledge on the structural types of FCS oligosaccharides and facilitates the exploration of the structure\u2013activity relationship in the future.<\/jats:p>","DOI":"10.3390\/md22040184","type":"journal-article","created":{"date-parts":[[2024,4,19]],"date-time":"2024-04-19T10:53:17Z","timestamp":1713523997000},"page":"184","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Chemical Synthesis of Fucosylated Chondroitin Sulfate Tetrasaccharide with Fucosyl Branch at the 6-OH of GalNAc Residue"],"prefix":"10.3390","volume":"22","author":[{"given":"Changlun","family":"Lv","sequence":"first","affiliation":[{"name":"Key Laboratory of Marine Drugs, Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaona","family":"Li","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs, Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Guoqing","family":"Yang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs, Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Haijiao","family":"Chen","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs, Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8102-137X","authenticated-orcid":false,"given":"Chunxia","family":"Li","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs, Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"},{"name":"Laboratory of Marine Drugs and Bioproducts of Qingdao Pilot National Laboratory for Marine Science and Technology, Qingdao 266237, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,4,19]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"232","DOI":"10.3390\/md12010232","article-title":"Holothurian Fucosylated Chondroitin Sulfate","volume":"12","author":"Pomin","year":"2014","journal-title":"Mar. Drugs"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"862","DOI":"10.1016\/j.carbpol.2011.08.082","article-title":"Structure and Effect of Sulfated Fucose Branches on Anticoagulant Activity of the Fucosylated Chondroitin Sulfate from Sea Cucumber Thelenata Ananas","volume":"87","author":"Wu","year":"2012","journal-title":"Carbohydr. Polym."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"688","DOI":"10.1016\/j.carbpol.2010.08.040","article-title":"Comparison of Structures and Anticoagulant Activities of Fucosylated Chondroitin Sulfates from Different Sea Cucumbers","volume":"83","author":"Chen","year":"2011","journal-title":"Carbohydr. Polym."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"399","DOI":"10.1016\/j.carbpol.2016.07.076","article-title":"Structural Characterization of Fucosylated Chondroitin Sulfates from Sea Cucumbers Apostichopus Japonicus and Actinopyga Mauritiana","volume":"153","author":"Ustyuzhanina","year":"2016","journal-title":"Carbohydr. Polym."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1016\/j.carbpol.2017.02.003","article-title":"The Structure of a Fucosylated Chondroitin Sulfate from the Sea Cucumber Cucumaria Frondosa","volume":"165","author":"Ustyuzhanina","year":"2017","journal-title":"Carbohydr. Polym."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1160","DOI":"10.1016\/j.carbpol.2017.10.100","article-title":"A Novel Structural Fucosylated Chondroitin Sulfate from Holothuria Mexicana and Its Effects on Growth Factors Binding and Anticoagulation","volume":"181","author":"Li","year":"2018","journal-title":"Carbohydr. Polym."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"28284","DOI":"10.1074\/jbc.M114.572297","article-title":"Fucosylated Chondroitin Sulfates from the Body Wall of the Sea Cucumber Holothuria Forskali Conformation, Selectin Binding, and Biological Activity","volume":"289","author":"Panagos","year":"2014","journal-title":"J. Biol. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"14984","DOI":"10.1074\/jbc.M610560200","article-title":"Selectin Blocking Activity of a Fucosylated Chondroitin Sulfate Glycosaminoglycan from Sea Cucumber Effect on Tumor Metastasis and Neutrophil Recruitment","volume":"282","author":"Borsig","year":"2007","journal-title":"J. Biol. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1647","DOI":"10.3390\/md10081647","article-title":"Preparation and Characterization of O-Acylated Fucosylated Chondroitin Sulfate from Sea Cucumber","volume":"10","author":"Gao","year":"2012","journal-title":"Mar. Drugs"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1016\/0021-9150(96)05897-2","article-title":"High Affinity of a Fucosylated Chondroitin Sulfate for Plasma Low Density Lipoprotein","volume":"126","author":"Tovar","year":"1996","journal-title":"Atherosclerosis"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"332","DOI":"10.1055\/s-0037-1614016","article-title":"Modulation of Vascular Human Endothelial and Rat Smooth Muscle Cell Growth by a Fucosylated Chondroitin Sulfate from Echinoderm","volume":"84","author":"Drouet","year":"2000","journal-title":"Thromb. Haemost."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"12880","DOI":"10.1002\/anie.201807546","article-title":"Synthesis of Fucosylated Chondroitin Sulfate Nonasaccharide as a Novel Anticoagulant Targeting Intrinsic Factor Xase Complex","volume":"57","author":"Zhang","year":"2018","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"112796","DOI":"10.1016\/j.ejmech.2020.112796","article-title":"The Components and Activities Analysis of a Novel Anticoagulant Candidate dHG-5","volume":"207","author":"Sun","year":"2020","journal-title":"Eur. J. Med. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"121304","DOI":"10.1016\/j.carbpol.2023.121304","article-title":"Branch Distribution Pattern and Anticoagulant Activity of a Fucosylated Chondroitin Sulfate from Phyllophorella Kohkutiensis","volume":"321","author":"Lan","year":"2023","journal-title":"Carbohydr. Polym."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"649","DOI":"10.1016\/j.carres.2009.11.030","article-title":"Preparation and Characterization of Molecular Weight Fractions of Glycosaminoglycan from Sea Cucumber Thelenata Ananas Using Free Radical Depolymerization","volume":"345","author":"Wu","year":"2010","journal-title":"Carbohydr. Res."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1427","DOI":"10.1016\/j.carbpol.2015.04.002","article-title":"\u03b2-Eliminative Depolymerization of the Fucosylated Chondroitin Sulfate and Anticoagulant Activities of Resulting Fragments","volume":"127","author":"Gao","year":"2015","journal-title":"Carbohydr. Polym."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"3940","DOI":"10.1016\/j.tetlet.2013.05.064","article-title":"Synthesis of \u03b2-d-GalNAc(4,6-diS)(1\u20134)[\u03b1-l-Fuc(2,4-diS)(1\u20133)]-\u03b2-d-GlcA, a Novel Trisaccharide Unit of Chondroitin Sulfate with a Fucose Branch","volume":"54","author":"Tamura","year":"2013","journal-title":"Tetrahedron Lett."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"2877","DOI":"10.1039\/C9OB00057G","article-title":"Synthesis of Trisaccharide Repeating Unit of Fucosylated Chondroitin Sulfate","volume":"17","author":"He","year":"2019","journal-title":"Org. Biomol. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"15908","DOI":"10.1021\/acs.joc.0c01009","article-title":"Chemical Synthesis of Fucosylated Chondroitin Sulfate Oligosaccharides","volume":"85","author":"Zhang","year":"2020","journal-title":"J. Org. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2435","DOI":"10.1055\/a-1440-9386","article-title":"Convergent Synthesis of Branched \u03b2-Glucan Tridecasaccharides Ready for Conjugation","volume":"53","author":"Zhou","year":"2021","journal-title":"Synthesis"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"24859","DOI":"10.1002\/anie.202111549","article-title":"Synthesis of a Tridecasaccharide Lipooligosaccharide Antigen from the Opportunistic Pathogen Mycobacterium Kansasii","volume":"60","author":"Shen","year":"2021","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"2335","DOI":"10.1021\/acs.orglett.9b00617","article-title":"Orthogonal One-Pot Synthesis of Oligosaccharides Based on Glycosyl Ortho-Alkynylbenzoates","volume":"21","author":"Zhang","year":"2019","journal-title":"Org. Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"3064","DOI":"10.1021\/jo991812k","article-title":"Efficient Synthesis of 3,6-Dideoxy-Beta-D-Arabino-Hexopyranosyl-Terminated LacdiNac Glycan Chains of the Trichinella Spiralis Parasite","volume":"65","author":"Nitz","year":"2000","journal-title":"J. Org. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"2270","DOI":"10.1021\/ol4008475","article-title":"2,2-Dimethyl-4-(4-Methoxy-Phenoxy) Butanoate and 2,2-Dimethyl-4-Azido Butanoate: Two New Pivaloate-Ester-like Protecting Groups","volume":"15","author":"Castelli","year":"2013","journal-title":"Org. Lett."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"12818","DOI":"10.1002\/chem.202000291","article-title":"Chemo-Enzymatic Synthesis of S. Mansoni O-Glycans and Their Evaluation as Ligands for C-Type Lectin Receptors MGL, DC-SIGN, and DC-SIGNR","volume":"26","author":"Pham","year":"2020","journal-title":"Chem. Eur. J."},{"key":"ref_26","first-page":"1","article-title":"Synthesis of fucosylated chondroitin sulfate trisaccharide","volume":"39","author":"Lv","year":"2020","journal-title":"Chin. J. Mar. Drugs"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1707","DOI":"10.1002\/(SICI)1521-3773(19980703)37:12<1707::AID-ANIE1707>3.0.CO;2-V","article-title":"Parallel Synthesis of Sialyl Lewis X Mimetics on a Solid Phase: Access to a Library of Fucopeptides","volume":"37","author":"Lampe","year":"1998","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_28","first-page":"115","article-title":"Synthesis of a Tetra- and a Nona-Saccharide Which Contain \u03b1-l-Fucopyranosyl Groups and Are Part of the Complex Type of Carbohydrate Moiety of Glycoproteins","volume":"139","year":"1985","journal-title":"Carbohydr. Res."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"2165","DOI":"10.1021\/ol049380+","article-title":"Thioglycuronides: Synthesis and Application in the Assembly of Acidic Oligosaccharides","volume":"6","author":"Boltje","year":"2004","journal-title":"Org. Lett."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"928","DOI":"10.1021\/acs.orglett.5b00031","article-title":"Synthesis of Staphylococcus Aureus Type 5 Trisaccharide Repeating Unit: Solving the Problem of Lactamization","volume":"17","author":"Gagarinov","year":"2015","journal-title":"Org. Lett."}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/22\/4\/184\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T14:31:11Z","timestamp":1760106671000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/22\/4\/184"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,4,19]]},"references-count":30,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2024,4]]}},"alternative-id":["md22040184"],"URL":"https:\/\/doi.org\/10.3390\/md22040184","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,4,19]]}}}