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Heparin, a naturally occurring, highly sulfated GAG, remains widely used as a clinical anticoagulant. However, risks of contamination, variable pharmacological response, and its adverse side effects have motivated the development of synthetic alternatives. Earlier reports of heparin-mimicking polymers have focused on either incorporating sulfate groups via postpolymerization methods or polymerizing free sulfonic acid-containing monomers via RAFT and ROMP. Synthesis using more sensitive polymerization techniques such as ATRP, NMP, and NCA-ROP, which require polymerization of protected sulfate-containing monomers, remains challenging and largely unexplored. Herein, we report a novel synthetic methodology to prepare mannose-6-sulfate (M6S)-based glycopolypeptides as a structural mimic of heparin. Initially, the protected sulfate group was introduced, particularly at the 6-position of mannose, and an M6S-based N-carboxyanhydride (NCA) monomer was prepared. Further, the protected glycopolypeptides were synthesized via NCA-ROP techniques. The fully water-soluble sulfated M6S glycopolypeptides, subsequently obtained after deprotection steps, exhibited minimal cytotoxicity toward mammalian cells and negligible hemolytic activity, underscoring their potential suitability for biomedical applications. Furthermore, both aPTT and PT assays indicate that these synthetic materials can act as anticoagulants by significantly prolonging clotting times with performance comparable to that of heparin. The control mannose glycopolypeptides exhibited no activity, demonstrating the importance of sulfate groups in achieving anticoagulation. The mechanistic investigations elucidated the anticoagulation pathway to be dependent on factors IIa and Xa. This methodology of developing sulfated glycopolypeptides might bring in more valuable therapeutics for antiviral or anticancer materials.<\/jats:p>","DOI":"10.1021\/acs.biomac.6c00475","type":"journal-article","created":{"date-parts":[[2026,7,6]],"date-time":"2026-07-06T17:25:22Z","timestamp":1783358722000},"page":"5263-5275","source":"Crossref","is-referenced-by-count":0,"title":["Controlled Synthesis\nof Sulfated Glycopolypeptides\nas Heparin Mimics via\n                    <i>N<\/i>\n                    -Carboxyanhydride ROP\nfor Anticoagulant Property"],"prefix":"10.1021","volume":"27","author":[{"given":"Abinash","family":"Padhy","sequence":"first","affiliation":[{"name":"Indian Institute of Science Education and Research Kolkata , , Nadia, , ,","place":["Mohanpur, West Bengal, India, 741246"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Abhishek","family":"Shaw","sequence":"additional","affiliation":[{"name":"Council of Scientific and Industrial Research (CSIR)-Indian Institute of Chemical Biology (IICB) , , ,","place":["Kolkata, India, 700032"]},{"name":"Academy of Scientific and Innovative Research (AcSIR) , ,","place":["Ghaziabad, India, 201002"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pallavi","family":"Kumari","sequence":"additional","affiliation":[{"name":"Indian Institute of Science Education and Research Kolkata , , Nadia, , ,","place":["Mohanpur, West Bengal, India, 741246"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0005-6152-5569","authenticated-orcid":true,"given":"Aritra","family":"Konar","sequence":"additional","affiliation":[{"name":"Indian Institute of Science Education and Research Kolkata , , Nadia, , ,","place":["Mohanpur, West Bengal, India, 741246"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rounak","family":"Mukhopadhyay","sequence":"additional","affiliation":[{"name":"Indian Institute of Science Education and Research Kolkata , , Nadia, , ,","place":["Mohanpur, West Bengal, India, 741246"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2424-2851","authenticated-orcid":true,"given":"Sujoy K.","family":"Das","sequence":"additional","affiliation":[{"name":"Council of Scientific and Industrial Research (CSIR)-Indian Institute of Chemical Biology (IICB) , , ,","place":["Kolkata, India, 700032"]},{"name":"Academy of Scientific and Innovative Research (AcSIR) , ,","place":["Ghaziabad, India, 201002"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3729-1820","authenticated-orcid":true,"given":"Sayam","family":"Sen Gupta","sequence":"additional","affiliation":[{"name":"Indian Institute of Science Education and Research Kolkata , , Nadia, , ,","place":["Mohanpur, West Bengal, India, 741246"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,7,6]]},"reference":[{"issue":"2","key":"2026081008071974300_cit1","doi-asserted-by":"publisher","first-page":"196","DOI":"10.3390\/md9020196","article-title":"Chemical Structures and Bioactivities\nof Sulfated Polysaccharides from Marine Algae","volume":"9","author":"Jiao","year":"2011","journal-title":"Mar. 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Cell. Physiol."},{"issue":"3","key":"2026081008071974300_cit24","doi-asserted-by":"publisher","first-page":"311","DOI":"10.1002\/jbm.820230304","article-title":"Properties and biological inteactions of polyurethane\nanionomers: Effect of sulfonate incorporation","volume":"23","author":"Grasel","year":"1989","journal-title":"J. Biomed. Mater. 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Macromol."},{"issue":"2","key":"2026081008071974300_cit28","doi-asserted-by":"publisher","first-page":"1009","DOI":"10.1021\/acs.biomac.9b01688","article-title":"Anticoagulant Heparin Mimetics via\nRAFT Polymerization","volume":"21","author":"Nahain","year":"2020","journal-title":"Biomacromolecules"},{"issue":"9","key":"2026081008071974300_cit29","doi-asserted-by":"publisher","first-page":"2000110","DOI":"10.1002\/mabi.202000110","article-title":"Sulfonated RAFT Copolymers as Heparin\nMimetics: Synthesis, Reactivity Ratios, and Anticoagulant Activity","volume":"20","author":"Nahain","year":"2020","journal-title":"Macromol. Biosci."},{"issue":"1","key":"2026081008071974300_cit30","doi-asserted-by":"publisher","first-page":"23","DOI":"10.1021\/bc010008d","article-title":"Novel Functional\nBiodegradable Polymer: Synthesis and Anticoagulant Activity of Poly(\u03b3-Glutamic\nAcid)sulfonate (\u03b3-PGA-sulfonate)","volume":"13","author":"Matsusaki","year":"2002","journal-title":"Bioconjugate\nChem."},{"issue":"4","key":"2026081008071974300_cit31","doi-asserted-by":"publisher","first-page":"472","DOI":"10.1002\/jbm.a.33060","article-title":"Enhancing blood\ncompatibility of biodegradable polymers by introducing sulfobetaine","volume":"97A","author":"Cao","year":"2011","journal-title":"J. Biomed. Mater. Res., Part A"},{"issue":"4","key":"2026081008071974300_cit32","doi-asserted-by":"publisher","first-page":"393","DOI":"10.1021\/bc960031c","article-title":"Synthesis and Anticoagulant\nActivity of Sulfated Glucoside-Bearing Polymer","volume":"7","author":"Akashi","year":"1996","journal-title":"Bioconjugate Chem."},{"issue":"45","key":"2026081008071974300_cit33","doi-asserted-by":"publisher","first-page":"11796","DOI":"10.1002\/anie.201306968","article-title":"Tailored\nGlycopolymers as Anticoagulant Heparin Mimetics","volume":"52","author":"Oh","year":"2013","journal-title":"Angew. Chem., Int. Ed."},{"issue":"5","key":"2026081008071974300_cit34","doi-asserted-by":"publisher","first-page":"1065","DOI":"10.1021\/bm025561s","article-title":"Glycosaminoglycan\nMimetic Biomaterials. 4. Synthesis of Sulfated Lactose-Based Glycopolymers\nThat Exhibit Anticoagulant Activity","volume":"3","author":"Sun","year":"2002","journal-title":"Biomacromolecules"},{"issue":"5","key":"2026081008071974300_cit35","doi-asserted-by":"publisher","first-page":"954","DOI":"10.1021\/bc0499275","article-title":"Facile Synthesis\nof Chain-End Functionalized Glycopolymers for Site-Specific Bioconjugation","volume":"15","author":"Hou","year":"2004","journal-title":"Bioconjugate Chem."},{"issue":"24","key":"2026081008071974300_cit36","doi-asserted-by":"publisher","first-page":"5230","DOI":"10.1002\/pola.26953","article-title":"Synthesis of a polyurea\nfrom a glucose- or mannose-containing N-alkyl urea peptoid oligomer","volume":"51","author":"Huang","year":"2013","journal-title":"J. Polym. Sci., Part A: polym. Chem."},{"issue":"12","key":"2026081008071974300_cit37","doi-asserted-by":"publisher","first-page":"4455","DOI":"10.1021\/bm501245v","article-title":"Synthesis\nand Anticoagulant Activity of Polyureas Containing Sulfated Carbohydrates","volume":"15","author":"Huang","year":"2014","journal-title":"Biomacromolecules"},{"issue":"23","key":"2026081008071974300_cit38","doi-asserted-by":"publisher","first-page":"3897","DOI":"10.1039\/C6PY00616G","article-title":"Blood compatibility\nof heparin-inspired, lactose containing, polyureas depends on the\nchemistry of the polymer backbone","volume":"7","author":"Huang","year":"2016","journal-title":"Polym. Chem."},{"issue":"1","key":"2026081008071974300_cit39","doi-asserted-by":"publisher","first-page":"244","DOI":"10.1021\/acsami.8b17625","article-title":"Specific Inhibition of Heparanase\nby a Glycopolymer\nwith Well-Defined Sulfation Pattern Prevents Breast Cancer Metastasis\nin Mice","volume":"11","author":"Loka","year":"2019","journal-title":"ACS Appl. Mater. Interfaces"},{"issue":"8","key":"2026081008071974300_cit40","doi-asserted-by":"publisher","first-page":"7049","DOI":"10.1021\/acsabm.5c00771","article-title":"Heparanase-Inhibiting Polymeric Heparan\nSulfate Mimetic Attenuates Myeloma Tumor Growth and Bone Metastasis","volume":"8","author":"Singh","year":"2025","journal-title":"ACS Appl. Bio Mater."},{"key":"2026081008071974300_cit41","doi-asserted-by":"publisher","first-page":"141521","DOI":"10.1016\/j.ijbiomac.2025.141521","article-title":"Nanoengineered and\nhighly porous 3D chitosan-graphene scaffold for enhanced antibacterial\nactivity and rapid hemostasis","volume":"306","author":"Choudhary","year":"2025","journal-title":"Int. J. Biol.\nMacromol."},{"issue":"9","key":"2026081008071974300_cit42","doi-asserted-by":"publisher","first-page":"3583","DOI":"10.1021\/jo900122c","article-title":"Trichloroethyl\nGroup As a Protecting\nGroup for Sulfonates and Its Application to the Synthesis of a Disulfonate\nAnalog of the Tyrosine Sulfated PSGL-143\u201350 Peptide","volume":"74","author":"Ali","year":"2009","journal-title":"J. Org. Chem."},{"issue":"21","key":"2026081008071974300_cit43","doi-asserted-by":"publisher","first-page":"3503","DOI":"10.1002\/anie.200600153","article-title":"Introduction of 2,2,2-Trichloroethyl-Protected Sulfates\ninto Monosaccharides with a Sulfuryl Imidazolium Salt and Application\nto the Synthesis of Sulfated Carbohydrates","volume":"45","author":"Ingram","year":"2006","journal-title":"Angew. Chem., Int. Ed."},{"issue":"7","key":"2026081008071974300_cit44","doi-asserted-by":"publisher","first-page":"809","DOI":"10.1021\/acsmacrolett.6b00297","article-title":"Controlled Synthesis\nof End-Functionalized Mannose-6-phosphate Glycopolypeptides for Lysosome\nTargeting","volume":"5","author":"Das","year":"2016","journal-title":"ACS Macro Lett."},{"issue":"5","key":"2026081008071974300_cit45","doi-asserted-by":"publisher","first-page":"1810","DOI":"10.1039\/D2BM02110B","article-title":"Dual stimuli-responsive\ncross-linked nanoassemblies from an amphiphilic mannose-6-phosphate\nbased tri-block copolymer for lysosomal membrane permeabilization","volume":"11","author":"Mondal","year":"2023","journal-title":"Biomater. Sci."},{"issue":"3","key":"2026081008071974300_cit46","doi-asserted-by":"publisher","first-page":"383","DOI":"10.1021\/acs.bioconjchem.4c00430","article-title":"Lysosome-Specific\nDelivery of \u03b2-Glucosidase Enzyme Using Protein-Glycopolypeptide\nConjugate via Protein Engineering and Bioconjugation","volume":"36","author":"Padhy","year":"2025","journal-title":"Bioconjugate Chem."},{"issue":"17","key":"2026081008071974300_cit47","doi-asserted-by":"publisher","first-page":"6479","DOI":"10.1021\/jo9014112","article-title":"O- and N-Sulfations\nof Carbohydrates Using Sulfuryl Imidazolium Salts","volume":"74","author":"Ingram","year":"2009","journal-title":"J. Org. Chem."},{"issue":"12","key":"2026081008071974300_cit48","doi-asserted-by":"publisher","first-page":"3668","DOI":"10.1021\/bm101123k","article-title":"General Method for Purification of \u03b1-Amino acid-N-carboxyanhydrides\nUsing Flash Chromatography","volume":"11","author":"Kramer","year":"2010","journal-title":"Biomacromolecules"},{"issue":"1","key":"2026081008071974300_cit49","doi-asserted-by":"publisher","first-page":"5810","DOI":"10.1038\/s41467-021-25689-y","article-title":"A moisture-tolerant\nroute to unprotected \u03b1\/\u03b2-amino acid N-carboxyanhydrides\nand facile synthesis of hyperbranched polypeptides","volume":"12","author":"Tian","year":"2021","journal-title":"Nat. Commun."},{"issue":"5","key":"2026081008071974300_cit50","doi-asserted-by":"publisher","first-page":"1287","DOI":"10.1021\/bm201813s","article-title":"Controlled\nSynthesis of O-Glycopolypeptide\nPolymers and Their Molecular Recognition by Lectins","volume":"13","author":"Pati","year":"2012","journal-title":"Biomacromolecules"},{"issue":"4","key":"2026081008071974300_cit51","doi-asserted-by":"publisher","first-page":"805","DOI":"10.1039\/c0py00412j","article-title":"Synthesis of glycopolypeptides\nby the ring opening polymerization of O-glycosylated-\u03b1-amino\nacid N-carboxyanhydride (NCA)","volume":"2","author":"Pati","year":"2011","journal-title":"Polym. Chem."},{"issue":"22","key":"2026081008071974300_cit52","doi-asserted-by":"publisher","first-page":"6322","DOI":"10.1039\/D0BM01469A","article-title":"Amphiphilic\nmannose-6-phosphate glycopolypeptide-based\nbioactive and responsive self-assembled nanostructures for controlled\nand targeted lysosomal cargo delivery","volume":"8","author":"Mondal","year":"2020","journal-title":"Biomater.\nSci."},{"issue":"36","key":"2026081008071974300_cit53","doi-asserted-by":"publisher","first-page":"8952","DOI":"10.1039\/D4TB01233J","article-title":"Design and synthesis of a shikimoyl-functionalized\ncationic di-block copolypeptide for cancer cell specific gene transfection","volume":"12","author":"Padhy","year":"2024","journal-title":"J. Mater. Chem. 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