{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,27]],"date-time":"2026-09-27T14:54:38Z","timestamp":1790520878996,"version":"4.1.0"},"reference-count":80,"publisher":"American Chemical Society (ACS)","issue":"6","funder":[{"DOI":"10.13039\/100006151","name":"Basic Energy Sciences","doi-asserted-by":"publisher","award":["DE-AC02-06CH11357"],"award-info":[{"award-number":["DE-AC02-06CH11357"]}],"id":[{"id":"10.13039\/100006151","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Org. Chem."],"published-print":{"date-parts":[[2016,3,18]]},"DOI":"10.1021\/acs.joc.5b02375","type":"journal-article","created":{"date-parts":[[2016,3,4]],"date-time":"2016-03-04T13:17:35Z","timestamp":1457097455000},"page":"2261-2279","source":"Crossref","is-referenced-by-count":44,"title":["Structural Basis of Duplex Thermodynamic Stability and Enhanced Nuclease Resistance of 5\u2032-<i>C<\/i>-Methyl Pyrimidine-Modified Oligonucleotides"],"prefix":"10.1021","volume":"81","author":[{"given":"Alexander V.","family":"Kel\u2032in","sequence":"first","affiliation":[{"name":"Alnylam Pharmaceuticals, 300\rThird Street, Cambridge, Massachusetts 02142, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ivan","family":"Zlatev","sequence":"additional","affiliation":[{"name":"Alnylam Pharmaceuticals, 300\rThird Street, Cambridge, Massachusetts 02142, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Joel","family":"Harp","sequence":"additional","affiliation":[{"name":"Department\rof Biochemistry and Center for Structural Biology, Vanderbilt University, School of Medicine, Nashville, Tennessee 37232, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Muthusamy","family":"Jayaraman","sequence":"additional","affiliation":[{"name":"Alnylam Pharmaceuticals, 300\rThird Street, Cambridge, Massachusetts 02142, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anna","family":"Bisbe","sequence":"additional","affiliation":[{"name":"Alnylam Pharmaceuticals, 300\rThird Street, Cambridge, Massachusetts 02142, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jonathan","family":"O\u2032Shea","sequence":"additional","affiliation":[{"name":"Alnylam Pharmaceuticals, 300\rThird Street, Cambridge, Massachusetts 02142, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nate","family":"Taneja","sequence":"additional","affiliation":[{"name":"Alnylam Pharmaceuticals, 300\rThird Street, Cambridge, Massachusetts 02142, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rajar M.","family":"Manoharan","sequence":"additional","affiliation":[{"name":"Alnylam Pharmaceuticals, 300\rThird Street, Cambridge, Massachusetts 02142, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Saeed","family":"Khan","sequence":"additional","affiliation":[{"name":"Department\rof Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Klaus","family":"Charisse","sequence":"additional","affiliation":[{"name":"Alnylam Pharmaceuticals, 300\rThird Street, Cambridge, Massachusetts 02142, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martin A.","family":"Maier","sequence":"additional","affiliation":[{"name":"Alnylam Pharmaceuticals, 300\rThird Street, Cambridge, Massachusetts 02142, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martin","family":"Egli","sequence":"additional","affiliation":[{"name":"Department\rof Biochemistry and Center for Structural Biology, Vanderbilt University, School of Medicine, Nashville, Tennessee 37232, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kallanthottathil G.","family":"Rajeev","sequence":"additional","affiliation":[{"name":"Alnylam Pharmaceuticals, 300\rThird Street, Cambridge, Massachusetts 02142, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Muthiah","family":"Manoharan","sequence":"additional","affiliation":[{"name":"Alnylam Pharmaceuticals, 300\rThird Street, Cambridge, Massachusetts 02142, United States"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2016,3,4]]},"reference":[{"key":"ref1\/cit1","doi-asserted-by":"publisher","DOI":"10.1001\/jama.2015.1241"},{"key":"ref2\/cit2","doi-asserted-by":"publisher","DOI":"10.1080\/02648725.2014.921495"},{"key":"ref3\/cit3","doi-asserted-by":"publisher","DOI":"10.1126\/scitranslmed.3008362"},{"key":"ref4\/cit4","unstructured":"http:\/\/www.alnylam.com\/capella\/presentations\/12-month-clinical-data-from-patisiran-phase-2-open-label-extension-ole-study\/."},{"key":"ref5\/cit5","unstructured":"http:\/\/www.alnylam.com\/capella\/presentations\/aln-at3-isth-june2015\/."},{"key":"ref6\/cit6","doi-asserted-by":"publisher","DOI":"10.1021\/ja505986a"},{"key":"ref7\/cit7","unstructured":"http:\/\/ir.arrowheadresearch.com\/eventdetail.cfm?eventid=151555."},{"key":"ref8\/cit8","doi-asserted-by":"publisher","DOI":"10.1017\/S0033583510000181"},{"key":"ref9\/cit9","doi-asserted-by":"publisher","DOI":"10.1016\/j.addr.2015.04.012"},{"key":"ref10\/cit10","doi-asserted-by":"publisher","DOI":"10.1089\/nat.2014.0506"},{"key":"ref11\/cit11","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms4459"},{"key":"ref12\/cit12","doi-asserted-by":"publisher","DOI":"10.1038\/nbt0491-358"},{"key":"ref13\/cit13","doi-asserted-by":"publisher","DOI":"10.1039\/c1ob05488k"},{"key":"ref14\/cit14","doi-asserted-by":"publisher","DOI":"10.1021\/bi026985+"},{"key":"ref15\/cit15","doi-asserted-by":"publisher","DOI":"10.1038\/nbt.3078"},{"key":"ref16\/cit16","doi-asserted-by":"publisher","DOI":"10.2174\/0929867013372409"},{"key":"ref17\/cit17","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.200900187"},{"key":"ref18\/cit18","unstructured":"Devi, G.InGene Therapy of Cancer;Walther, W.; Stein, U. S., Eds.Humana Press:New York, 2009; Vol.542, p351."},{"key":"ref19\/cit19","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gku235"},{"key":"ref20\/cit20","doi-asserted-by":"publisher","DOI":"10.1016\/0960-894X(94)80011-1"},{"key":"ref21\/cit21","doi-asserted-by":"publisher","DOI":"10.1016\/0141-8130(79)90013-8"},{"key":"ref22\/cit22","doi-asserted-by":"publisher","DOI":"10.1021\/ja904926e"},{"key":"ref23\/cit23","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.201300023"},{"key":"ref24\/cit24","doi-asserted-by":"publisher","DOI":"10.1016\/j.addr.2015.01.008"},{"key":"ref25\/cit25","doi-asserted-by":"publisher","DOI":"10.1089\/108729003321629638"},{"key":"ref26\/cit26","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkv298"},{"key":"ref27\/cit27","doi-asserted-by":"publisher","DOI":"10.1002\/0471264180.or055.01"},{"key":"ref28\/cit28","unstructured":"Beigelman, L.; Blatt, L.; Wang, G.PCT Int. Appl.WO2010108140, 2010."},{"key":"ref29\/cit29","unstructured":"Beigelman, L.; Blatt, L.; Wang, G.; Rajwanshi, V. K.; Dyatkina, N.; Smith, D. B.U.S. Pat. Appl. Publ.US 20120070411, 2012."},{"key":"ref30\/cit30","doi-asserted-by":"publisher","DOI":"10.1080\/07328318808056308"},{"key":"ref31\/cit31","first-page":"969","volume":"15","author":"Mikhailov S. N.","year":"1989","journal-title":"Bioorg. Khim."},{"key":"ref32\/cit32","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(96)00418-2"},{"key":"ref33\/cit33","doi-asserted-by":"publisher","DOI":"10.1021\/jo00109a003"},{"key":"ref34\/cit34","doi-asserted-by":"publisher","DOI":"10.1021\/cb5003027"},{"key":"ref35\/cit35","doi-asserted-by":"publisher","DOI":"10.1080\/15257779508012498"},{"key":"ref36\/cit36","doi-asserted-by":"publisher","DOI":"10.1021\/jo4012333"},{"key":"ref37\/cit37","doi-asserted-by":"publisher","DOI":"10.1039\/c1ob06148h"},{"key":"ref38\/cit38","doi-asserted-by":"publisher","DOI":"10.1021\/jo500794v"},{"key":"ref39\/cit39","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkv162"},{"key":"ref40\/cit40","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201006519"},{"key":"ref41\/cit41","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2003.11.007"},{"key":"ref42\/cit42","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(02)00080-0"},{"key":"ref43\/cit43","doi-asserted-by":"publisher","DOI":"10.1016\/S0008-6215(00)82160-6"},{"key":"ref44\/cit44","doi-asserted-by":"publisher","DOI":"10.1021\/jo00917a003"},{"key":"ref45\/cit45","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19960790720"},{"key":"ref46\/cit46","doi-asserted-by":"publisher","DOI":"10.1055\/s-1997-1003"},{"key":"ref47\/cit47","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/11.21.7611"},{"key":"ref48\/cit48","first-page":"895","volume":"5","author":"Karpeiskii M. Y.","year":"1979","journal-title":"Bioorg. Khim."},{"key":"ref49\/cit49","first-page":"668","volume":"16","author":"Padyukova N. S.","year":"1990","journal-title":"Bioorg. Khim."},{"key":"ref50\/cit50","doi-asserted-by":"publisher","DOI":"10.1021\/jo500089t"},{"key":"ref51\/cit51","doi-asserted-by":"publisher","DOI":"10.1021\/ol0067639"},{"key":"ref52\/cit52","doi-asserted-by":"crossref","first-page":"101","DOI":"10.3998\/ark.5550190.0007.211","author":"Halligan K.","year":"2006","journal-title":"ARKIVOC"},{"key":"ref53\/cit53","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.200490269"},{"key":"ref54\/cit54","doi-asserted-by":"publisher","DOI":"10.1021\/ol301937v"},{"key":"ref55\/cit55","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(99)00229-X"},{"key":"ref56\/cit56","doi-asserted-by":"publisher","DOI":"10.1021\/jo9510548"},{"key":"ref57\/cit57","first-page":"976","volume":"15","author":"Dzhavadova G. M.","year":"1989","journal-title":"Bioorg. Khim."},{"key":"ref58\/cit58","doi-asserted-by":"publisher","DOI":"10.1021\/ja00778a043"},{"key":"ref59\/cit59","doi-asserted-by":"publisher","DOI":"10.1021\/ja00788a038"},{"key":"ref60\/cit60","doi-asserted-by":"publisher","DOI":"10.1021\/bi00718a027"},{"key":"ref61\/cit61","doi-asserted-by":"publisher","DOI":"10.1107\/S056774086900416X"},{"key":"ref62\/cit62","doi-asserted-by":"publisher","DOI":"10.1021\/jm101207e"},{"key":"ref63\/cit63","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/25.22.4429"},{"key":"ref64\/cit64","doi-asserted-by":"publisher","DOI":"10.1021\/bi201810r"},{"key":"ref65\/cit65","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/23.11.2019"},{"key":"ref66\/cit66","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1097-0282(1998)48:4<234::AID-BIP4>3.0.CO;2-H"},{"key":"ref67\/cit67","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1002\/j.1460-2075.1991.tb07917.x","volume":"10","author":"Beese L. S.","year":"1991","journal-title":"EMBO J."},{"key":"ref68\/cit68","doi-asserted-by":"publisher","DOI":"10.1016\/S0092-8674(00)81134-4"},{"key":"ref69\/cit69","doi-asserted-by":"publisher","DOI":"10.1006\/jmbi.1997.1586"},{"key":"ref70\/cit70","doi-asserted-by":"publisher","DOI":"10.1021\/bi981537g"},{"key":"ref71\/cit71","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc32286b"},{"key":"ref72\/cit72","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.96.25.14240"},{"key":"ref73\/cit73","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.20084"},{"key":"ref74\/cit74","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)77667-2"},{"key":"ref75\/cit75","unstructured":"Wang, G.; Smith, D. B.; Beigelman, L.; Deval, J.; Prhavc, M.U.S. Pat. Appl. Publ.US20130165400, 2013."},{"key":"ref76\/cit76","unstructured":"Manoharan, M.; Lackey, J.; Rajeev, K. G.; Zlatev, I.PCT Int. Appl.WO2011133868, 2011."},{"key":"ref77\/cit77","doi-asserted-by":"publisher","DOI":"10.1021\/jm5017279"},{"key":"ref78\/cit78","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2014.04.042"},{"key":"ref79\/cit79","doi-asserted-by":"publisher","DOI":"10.1021\/ja5035717"},{"key":"ref80\/cit80","first-page":"678","volume":"17","author":"Chidgeavadze Z. G.","year":"1991","journal-title":"Bioorg. Khim."}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.5b02375","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,4,17]],"date-time":"2023-04-17T18:33:18Z","timestamp":1681756398000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/acs.joc.5b02375"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2016,3,4]]},"references-count":80,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2016,3,18]]}},"alternative-id":["10.1021\/acs.joc.5b02375"],"URL":"https:\/\/doi.org\/10.1021\/acs.joc.5b02375","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2016,3,4]]}}}