{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T08:39:59Z","timestamp":1789547999521,"version":"build-2803163510"},"reference-count":55,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2025,12,18]],"date-time":"2025-12-18T00:00:00Z","timestamp":1766016000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"crossref","award":["U21A20297"],"award-info":[{"award-number":["U21A20297"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"crossref"}]},{"name":"Taishan Scholar Climbing Project","award":["TSPD20210304"],"award-info":[{"award-number":["TSPD20210304"]}]},{"name":"Young Project","award":["TSQN202306099"],"award-info":[{"award-number":["TSQN202306099"]}]},{"DOI":"10.13039\/501100012226","name":"Fundamental Research Funds for the Central Universities","doi-asserted-by":"crossref","award":["202461054"],"award-info":[{"award-number":["202461054"]}],"id":[{"id":"10.13039\/501100012226","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>The ongoing COVID-19 pandemic, caused by SARS-CoV-2, continues to pose major global health challenges despite extensive vaccination efforts. Variant escape, waning immunity, and reduced vaccine efficacy in immunocompromised populations underscore the urgent need for complementary antiviral therapeutics. Here, we report the design, synthesis, and biological evaluation of precision-engineered dermatan sulfate (DS)-mimetic glycopolymers as multi-targeted inhibitors of SARS-CoV-2. Guided by molecular docking and virtual screening, sulfation at the C2 and C4 positions of iduronic acid was identified as critical for binding to the viral spike protein and inhibiting host and viral enzymes, including heparanase (HPSE) and main protease (Mpro). Chemically synthesized DS disaccharides were covalently grafted onto polymer scaffolds via a post-modification strategy, yielding glycopolymers with well-defined assembly that form uniform nanoparticles under physiological conditions. Surface plasmon resonance and pseudovirus assays revealed strong binding to the viral spike protein (KD \u2248 177 nM), potent viral neutralization, and minimal cytotoxicity. Cellular uptake studies further demonstrated efficient internalization of nanoparticles and intracellular inhibition of HPSE and Mpro. These results establish a modular, non-anticoagulant, and glycosaminoglycan-mimetic platform for the development of broad-spectrum antiviral agents to complement vaccination and enhance preparedness against emerging coronavirus variants.<\/jats:p>","DOI":"10.3390\/md23120486","type":"journal-article","created":{"date-parts":[[2025,12,18]],"date-time":"2025-12-18T16:42:05Z","timestamp":1766076125000},"page":"486","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Precision-Engineered Dermatan Sulfate-Mimetic Glycopolymers for Multi-Targeted SARS-CoV-2 Inhibition"],"prefix":"10.3390","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0009-0003-9645-5236","authenticated-orcid":false,"given":"Lihao","family":"Wang","sequence":"first","affiliation":[{"name":"Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotherapeutics, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lei","family":"Gao","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotherapeutics, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chendong","family":"Yang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotherapeutics, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mengfei","family":"Yin","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotherapeutics, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiqin","family":"Sun","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotherapeutics, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Luyao","family":"Yang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotherapeutics, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chanjuan","family":"Liu","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotherapeutics, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1831-8389","authenticated-orcid":false,"given":"Simon F. R.","family":"Hinkley","sequence":"additional","affiliation":[{"name":"The Ferrier Research Institute, Victoria University of Wellington, 69 Gracefield Road, Lower Hutt 5040, New Zealand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6372-9750","authenticated-orcid":false,"given":"Guangli","family":"Yu","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotherapeutics, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"},{"name":"Laboratory for Marine Drugs and Bioproducts, Qingdao Marine Science and Technology Center, Qingdao 266003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4377-3989","authenticated-orcid":false,"given":"Chao","family":"Cai","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotherapeutics, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"},{"name":"Laboratory for Marine Drugs and Bioproducts, Qingdao Marine Science and Technology Center, Qingdao 266003, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,12,18]]},"reference":[{"key":"ref_1","unstructured":"World Health Organization (2025, November 10). WHO Coronavirus (COVID-19) Dashboard. Available online: https:\/\/data.who.int\/dashboards\/covid19\/more-resources."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"114","DOI":"10.1007\/s40808-024-02236-4","article-title":"Assessing the potential seasonality of COVID-19 dynamic in Africa: A mathematical modeling study","volume":"11","author":"Montcho","year":"2025","journal-title":"Model. Earth Syst. Environ."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"8933","DOI":"10.1038\/s41467-025-63944-8","article-title":"Higher mortality following SARS-CoV-2 infection in rural versus urban dwellers persists for two years post-infection","volume":"16","author":"Anzalone","year":"2025","journal-title":"Nat. Commun."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"140946","DOI":"10.1016\/j.scitotenv.2020.140946","article-title":"SARS-CoV-2 in the environment: Modes of transmission, early detection and potential role of pollutions","volume":"744","author":"Alhosani","year":"2020","journal-title":"Sci. Total Environ."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"177","DOI":"10.1038\/d41586-021-00031-0","article-title":"Could new COVID variants undermine vaccines? Labs scramble to find out","volume":"589","author":"Callaway","year":"2021","journal-title":"Nature"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"741","DOI":"10.1126\/science.abe6522","article-title":"Immunological characteristics govern the transition of COVID-19 to endemicity","volume":"371","author":"Lavine","year":"2021","journal-title":"Science"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1085","DOI":"10.1056\/NEJMc2025179","article-title":"Rapid decay of anti\u2013SARS-CoV-2 antibodies in persons with mild COVID-19","volume":"383","author":"Ibarrondo","year":"2020","journal-title":"N. Engl. J. Med."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"207","DOI":"10.1038\/s41423-024-01132-2","article-title":"COVID-19 vaccines and beyond","volume":"21","author":"Liu","year":"2024","journal-title":"Cell. Mol. Immunol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"104903","DOI":"10.1016\/j.ebiom.2023.104903","article-title":"Dynamic immune landscape in vaccinated-BA.5-XBB.1.9.1 reinfections revealed a 5-month protection-duration against XBB infection and a shift in immune imprinting","volume":"99","author":"Cui","year":"2024","journal-title":"Ebiomedicine"},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Lang, J., Yang, N., Deng, J., Liu, K., Yang, P., Zhang, G., and Jiang, C. (2011). Inhibition of SARS pseudovirus cell entry by lactoferrin binding to heparan sulfate proteoglycans. PLoS ONE, 6.","DOI":"10.1371\/journal.pone.0023710"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"215","DOI":"10.1038\/s41586-020-2180-5","article-title":"Structure of the SARS-CoV-2 spike receptor-binding domain bound to the ACE2 receptor","volume":"581","author":"Lan","year":"2020","journal-title":"Nature"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"271","DOI":"10.1016\/j.cell.2020.02.052","article-title":"SARS-CoV-2 cell entry depends on ACE2 and TMPRSS2 and is blocked by a clinically proven protease inhibitor","volume":"181","author":"Hoffmann","year":"2020","journal-title":"Cell"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"e01373-23","DOI":"10.1128\/mbio.01373-23","article-title":"SARS-CoV-2 main protease cleaves MAGED2 to antagonize host antiviral defense","volume":"14","author":"Ju","year":"2023","journal-title":"mBio"},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"VK, P., Rath, S.P., and Abraham, P. (2021). Computational designing of a peptide that potentially blocks the entry of SARS-CoV, SARS-CoV-2 and MERS-CoV. PLoS ONE, 16.","DOI":"10.1371\/journal.pone.0251913"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"412","DOI":"10.1111\/febs.16599","article-title":"Core fucose-specific pholiota squarrosa lectin (PhoSL) as a potent broad-spectrum inhibitor of SARS-CoV-2 infection","volume":"290","author":"Yamasaki","year":"2023","journal-title":"FEBS J."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"105653","DOI":"10.1016\/j.antiviral.2023.105653","article-title":"Combining virtual screening with cis-\/trans-cleavage enzymatic assays effectively reveals broad-spectrum inhibitors that target the main proteases of SARS-CoV-2 and MERS-CoV","volume":"216","author":"Chang","year":"2023","journal-title":"Antivir. Res."},{"key":"ref_17","unstructured":"Varki, A., Cummings, R.D., Esko, J.D., Stanley, P., Hart, G.W., Aebi, M., Mohnen, D., Kinoshita, T., Packer, N.H., and Prestegard, J.H. (2022). Essentials of Glycobiology, Cold Spring Harbor Laboratory Press."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1043","DOI":"10.1016\/j.cell.2020.09.033","article-title":"SARS-CoV-2 infection depends on cellular heparan sulfate and ACE2","volume":"183","author":"Clausen","year":"2020","journal-title":"Cell"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"104873","DOI":"10.1016\/j.antiviral.2020.104873","article-title":"Characterization of heparin and severe acute respiratory syndrome-related coronavirus 2 (SARS-CoV-2) spike glycoprotein binding interactions","volume":"181","author":"Kim","year":"2020","journal-title":"Antivir. Res."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"50","DOI":"10.1038\/s41421-020-00192-8","article-title":"Sulfated polysaccharides effectively inhibit SARS-CoV-2 in vitro","volume":"6","author":"Kwon","year":"2020","journal-title":"Cell Discov."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1009","DOI":"10.1021\/acscentsci.1c00010","article-title":"Heparan sulfate proteoglycans as attachment factor for SARS-CoV-2","volume":"7","author":"Liu","year":"2021","journal-title":"ACS Cent. Sci."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1463","DOI":"10.1021\/acs.jnatprod.3c00151","article-title":"The sea cucumber thyonella gemmata contains a low anticoagulant sulfated fucan with high anti-SARS-CoV-2 actions against wild-type and delta variants","volume":"86","author":"Dwivedi","year":"2023","journal-title":"J. Nat. Prod."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"123703","DOI":"10.1016\/j.carbpol.2025.123703","article-title":"Role, binding properties, and potential therapeutical use of glycosaminoglycans and mimetics in SARS-CoV-2 infection. In memory of dr. Robert linhardt (1953\u20132025)","volume":"362","author":"Pomin","year":"2025","journal-title":"Carbohydr. Polym."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"626","DOI":"10.1111\/bph.15304","article-title":"Unfractionated heparin inhibits live wild type SARS-CoV-2 cell infectivity at therapeutically relevant concentrations","volume":"178","author":"Tree","year":"2021","journal-title":"Br. J. Pharmacol."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"e01987-20","DOI":"10.1128\/JVI.01987-20","article-title":"Effective inhibition of SARS-CoV-2 entry by heparin and enoxaparin derivatives","volume":"95","author":"Tandon","year":"2021","journal-title":"J. Virol."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1700","DOI":"10.1055\/s-0040-1721319","article-title":"Heparin inhibits cellular invasion by SARS-CoV-2: Structural dependence of the interaction of the spike S1 receptor-binding domain with heparin","volume":"120","author":"Su","year":"2020","journal-title":"Thromb. Haemost."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"117867","DOI":"10.1016\/j.carbpol.2021.117867","article-title":"Oversulfated dermatan sulfate and heparinoid in the starfish lysastrosoma anthosticta: Structures and anticoagulant activity","volume":"261","author":"Ustyuzhanina","year":"2021","journal-title":"Carbohydr. Polym."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"664","DOI":"10.1093\/glycob\/cwac030","article-title":"Functions of chondroitin\/dermatan sulfate containing GalNAc4,6-disulfate","volume":"32","author":"Habuchi","year":"2022","journal-title":"Glycobiology"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"120508","DOI":"10.1016\/j.carbpol.2022.120508","article-title":"A novel 4-O-endosulfatase with high potential for the structure-function studies of chondroitin sulfate\/dermatan sulfate","volume":"305","author":"Wei","year":"2023","journal-title":"Carbohydr. Polym."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"cwae024","DOI":"10.1093\/glycob\/cwae024","article-title":"The significant role of glycosaminoglycans in tooth development","volume":"34","author":"Inubushi","year":"2024","journal-title":"Glycobiology"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"572","DOI":"10.1093\/glycob\/cwz039","article-title":"Specificity and action pattern of heparanase bp, a \u03b2-glucuronidase from burkholderia pseudomallei","volume":"29","author":"Yu","year":"2019","journal-title":"Glycobiology"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"823","DOI":"10.1369\/0022155420937087","article-title":"Heparanase-enhanced shedding of syndecan-1 and its role in driving disease pathogenesis and progression","volume":"68","author":"Rangarajan","year":"2020","journal-title":"J. Histochem. Cytochem."},{"key":"ref_33","doi-asserted-by":"crossref","unstructured":"Vlodavsky, I., Sanderson, R.D., and Ilan, N. (2020). Heparanase: From Basic Research to Clinical Applications, Springer International Publishing.","DOI":"10.1007\/978-3-030-34521-1"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"e00057-22","DOI":"10.1128\/jvi.00057-22","article-title":"Heparanase blockade as a novel dual-targeting therapy for COVID-19","volume":"96","author":"Xiang","year":"2022","journal-title":"J. Virol."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"e202411760","DOI":"10.1002\/anie.202411760","article-title":"Synthesis of low-molecular-weight fucoidan analogue and its inhibitory activities against heparanase and SARS-CoV-2 infection","volume":"64","author":"Sugimoto","year":"2025","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_36","first-page":"132","article-title":"Clinical features of heparin-induced thrombocytopenia including risk factors for thrombosis","volume":"94","author":"Greinacher","year":"2017","journal-title":"Thromb. Haemost."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"15870","DOI":"10.1002\/anie.202102717","article-title":"Polysulfates block SARS-CoV-2 uptake through electrostatic interactions","volume":"60","author":"Nie","year":"2021","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1411","DOI":"10.1021\/acsmedchemlett.3c00319","article-title":"Heparan sulfate-mimicking glycopolymers bind SARS-CoV-2 spike protein in a length- and sulfation pattern-dependent manner","volume":"14","author":"Abdulsalam","year":"2023","journal-title":"ACS Med. Chem. Lett."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"4714","DOI":"10.1039\/D0PY00384K","article-title":"End-functionalised glycopolymers as glycosaminoglycan mimetics inhibit HeLa cell proliferation","volume":"11","author":"Yang","year":"2020","journal-title":"Polym. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Grant, O.C., Wentworth, D., Holmes, S.G., Kandel, R., Sehnal, D., Wang, X., Xiao, Y., Sheppard, P., Grelsson, T., and Coulter, A. (2025). Generating 3D models of carbohydrates with GLYCAM-web. bioRxiv.","DOI":"10.1101\/2025.05.08.652828"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"892","DOI":"10.1021\/acs.jctc.5b00834","article-title":"Vina-carb: Improving glycosidic angles during carbohydrate docking","volume":"12","author":"Nivedha","year":"2016","journal-title":"J. Chem. Theory Comput."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"2329","DOI":"10.1111\/jth.13555","article-title":"A century of heparin: Past, present and future","volume":"14","author":"Hemker","year":"2016","journal-title":"J. Thromb. Haemost."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"328","DOI":"10.1124\/pharmrev.122.000684","article-title":"Pharmacology of heparin and related drugs: An update","volume":"75","author":"Hogwood","year":"2023","journal-title":"Pharmacol. Rev."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"e202200351","DOI":"10.1002\/cbic.202200351","article-title":"Initial recognition and attachment of the zika virus to host cells: A molecular dynamics and quantum interaction approach","volume":"23","author":"Lans","year":"2022","journal-title":"Chembiochem"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"117R","DOI":"10.1093\/glycob\/cwf066","article-title":"Dermatan sulfate: New functions from an old glycosaminoglycan","volume":"12","author":"Trowbridge","year":"2002","journal-title":"Glycobiology"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"7559","DOI":"10.1021\/jo0340760","article-title":"Synthesis of Iduronic Acid Building Blocks for the Modular Assembly of Glycosaminoglycans","volume":"68","author":"Lohman","year":"2003","journal-title":"J. Org. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"6957","DOI":"10.1166\/jnn.2018.15458","article-title":"Role of particle\u2013particle interaction towards effective interpretation of Z-average and particle size distributions from dynamic light scattering (DLS) analysis","volume":"18","author":"Yeap","year":"2018","journal-title":"J. Nanosci. Nanotechnol."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"2129","DOI":"10.1021\/bm0701402","article-title":"Inhibition of alzheimer amyloid aggregation with sulfated glycopolymers","volume":"8","author":"Miura","year":"2007","journal-title":"Biomacromolecules"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"715","DOI":"10.1038\/nchem.2749","article-title":"A polymer nanoparticle with engineered affinity for a vascular endothelial growth factor (VEGF165)","volume":"9","author":"Koide","year":"2017","journal-title":"Nat. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1673","DOI":"10.1021\/acs.chemrev.5b00247","article-title":"Glycopolymer Nanobiotechnology","volume":"116","author":"Yoshiko","year":"2016","journal-title":"Chem. Rev."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"3275","DOI":"10.1039\/C6CS00165C","article-title":"Organizing multivalency in carbohydrate recognition","volume":"45","author":"Despras","year":"2016","journal-title":"Chem. Soc. Rev."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"120595","DOI":"10.1016\/j.saa.2021.120595","article-title":"Heparin interacts with the main protease of SARS-CoV-2 and inhibits its activity","volume":"267","author":"Li","year":"2022","journal-title":"Spectrochim. Acta Part A"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"27381","DOI":"10.1073\/pnas.2010470117","article-title":"Identify potent SARS-CoV-2 main protease inhibitors via accelerated free energy perturbation-based virtual screening of existing drugs","volume":"117","author":"Li","year":"2020","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"345","DOI":"10.1016\/j.carres.2006.09.025","article-title":"Recent studies on reaction pathways and applications of sugar orthoesters in synthesis of oligosaccharides","volume":"342","author":"Kong","year":"2007","journal-title":"Carbohydr. Res."},{"key":"ref_55","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."}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/23\/12\/486\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,12,20]],"date-time":"2025-12-20T05:24:08Z","timestamp":1766208248000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/23\/12\/486"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,12,18]]},"references-count":55,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2025,12]]}},"alternative-id":["md23120486"],"URL":"https:\/\/doi.org\/10.3390\/md23120486","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,12,18]]}}}