{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T21:40:22Z","timestamp":1792705222600,"version":"4.5.0"},"reference-count":46,"publisher":"American Chemical Society (ACS)","issue":"40","license":[{"start":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T00:00:00Z","timestamp":1791158400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100000165","name":"Division of Chemistry","doi-asserted-by":"publisher","award":["CHE-2404191"],"award-info":[{"award-number":["CHE-2404191"]}],"id":[{"id":"10.13039\/100000165","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000928","name":"Welch Foundation","doi-asserted-by":"publisher","award":["A-0001"],"award-info":[{"award-number":["A-0001"]}],"id":[{"id":"10.13039\/100000928","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000928","name":"Welch Foundation","doi-asserted-by":"publisher","award":["A-0923"],"award-info":[{"award-number":["A-0923"]}],"id":[{"id":"10.13039\/100000928","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,14]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>With an interest in sustainable polymers derived from nucleoside building blocks, d-thymidine and carbon disulfide (CS2) were used as synthetic precursors to construct a trans-fused, 6,5-membered bicyclic xanthate, 3\u2032,5\u2032-cyclic N3-(3-butenyl)-d-thymidine trans xanthate, for ring-opening polymerization (ROP) to yield stereo- and regiochemically defined homopolymer analogs of nucleic acids bearing thiocarbonate backbones. Screenings for CS2 insertion and succeeding cyclization to form the targeted monomer revealed two additional d-thymidine-derived cyclic moieties, including a xanthate and trithiocarbonate of cis-fused configurations, isolated in low yields. Therefore, ROP experiments using alkoxy-based initiators and organobase catalysts at room temperature and supporting DFT calculations for enthalpies of ring opening were extended to all three potential monomers, with only the trans-fused bicyclic xanthate undergoing ROP. Structural characterization by MALDI-TOF mass spectrometry and NMR spectroscopy of polymers obtained from ROPs of 3\u2032,5\u2032-cyclic N3-(3-butenyl)-d-thymidine trans xanthate conducted at or somewhat below ambient temperatures indicated the presence of linear and cyclic species having primarily dimeric 5\u2032,5\u2032-trithiocarbonate-co-3\u2032,3\u2032-thionocarbonate connectivities from an alternating C\u2013S and C\u2013O cleavage pathway. Other minor trithiocarbonate, xanthate, and thionocarbonate functionalities were proposed to arise from backbiting reactions and\/or minor regiorandom cleavages. In contrast, ROPs conducted at reduced temperatures (\u2264 \u221220 or \u221240 \u00b0C depending on the organobase) achieved selective C\u2013S cleavage to yield 3\u2032,5\u2032-xanthate-connected polymers of N3-(3-butenyl)-d-thymidine with more structural similarity to native DNA. These fundamental advances extend the breadth of nucleoside-derived polymers, emphasizing the influence of sulfur incorporation during monomer synthesis and upon subsequent ROPs, with outcomes being temperature-mediated alternating vs. unidirectional backbone compositional and structural regioregularity.<\/jats:p>","DOI":"10.1021\/jacs.6c15290","type":"journal-article","created":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T10:02:08Z","timestamp":1791194528000},"page":"43812-43821","source":"Crossref","is-referenced-by-count":0,"title":["Investigation of Sulfur-related Influences on the\nConstruction and Ring Opening of a Six-membered Cyclic Xanthate Derived\nfrom\n                    <scp>d<\/scp>\n                    -Thymidine and CS2"],"prefix":"10.1021","volume":"148","author":[{"given":"Autumn M.","family":"Andras","sequence":"first","affiliation":[{"name":"Texas A&M University , , , ,","place":["College Station, Texas, United States, 77843"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nehal","family":"Fatima","sequence":"additional","affiliation":[{"name":"Texas A&M University , , , ,","place":["College Station, Texas, United States, 77843"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kai-Hua Mick","family":"Kuo","sequence":"additional","affiliation":[{"name":"Texas A&M University , , , ,","place":["College Station, Texas, United States, 77843"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"David K.","family":"Tran","sequence":"additional","affiliation":[{"name":"Texas A&M University , , , ,","place":["College Station, Texas, United States, 77843"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9285-4895","authenticated-orcid":true,"given":"Donald J.","family":"Darensbourg","sequence":"additional","affiliation":[{"name":"Texas A&M University , , , ,","place":["College Station, Texas, United States, 77843"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4086-384X","authenticated-orcid":true,"given":"Karen L.","family":"Wooley","sequence":"additional","affiliation":[{"name":"Texas A&M University , , , ,","place":["College Station, Texas, United States, 77843"]},{"name":"Texas A&M University , , , ,","place":["College Station, Texas, United States, 77843"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,10,5]]},"reference":[{"issue":"3","key":"2026102217063993400_cit1","doi-asserted-by":"publisher","first-page":"238","DOI":"10.1038\/nbt.3765","article-title":"The chemical evolution of oligonucleotide therapies\nof clinical utility","volume":"35","author":"Khvorova","year":"2017","journal-title":"Nat. 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Selectivity for the production of copolymers vs. cyclic\nthiocarbonates","volume":"38","author":"Darensbourg","year":"2009","journal-title":"Dalton Trans."},{"issue":"16","key":"2026102217063993400_cit46","doi-asserted-by":"publisher","first-page":"5526","DOI":"10.1021\/acs.macromol.5b01251","article-title":"An Investigation of the Pathways\nfor Oxygen\/Sulfur Scramblings during the Copolymerization of Carbon\nDisulfide and Oxetane","volume":"48","author":"Luo","year":"2015","journal-title":"Macromolecules"}],"container-title":["Journal of the American Chemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jacs.6c15290","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/40\/43812\/68743010\/jacs.6c15290.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/40\/43812\/68743010\/jacs.6c15290.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T21:11:06Z","timestamp":1792703466000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jacsat\/article\/148\/40\/43812\/5444427\/Investigation-of-Sulfur-related-Influences-on-the"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,10,5]]},"references-count":46,"journal-issue":{"issue":"40","published-online":{"date-parts":[[2026,10,5]]},"published-print":{"date-parts":[[2026,10,14]]}},"URL":"https:\/\/doi.org\/10.1021\/jacs.6c15290","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,10,5]]}}}