{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,9]],"date-time":"2026-01-09T12:31:45Z","timestamp":1767961905896,"version":"3.49.0"},"reference-count":57,"publisher":"American Chemical Society (ACS)","issue":"11","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Org. Chem."],"published-print":{"date-parts":[[2012,6,1]]},"DOI":"10.1021\/jo300594b","type":"journal-article","created":{"date-parts":[[2012,5,15]],"date-time":"2012-05-15T20:56:02Z","timestamp":1337115362000},"page":"5074-5085","source":"Crossref","is-referenced-by-count":41,"title":["Synthesis and Antisense Properties of Fluoro Cyclohexenyl Nucleic Acid (F-CeNA), a Nuclease Stable Mimic of 2\u2032-Fluoro RNA"],"prefix":"10.1021","volume":"77","author":[{"given":"Punit P.","family":"Seth","sequence":"first","affiliation":[{"name":"Isis Pharmaceuticals, 2855 Gazelle Court,\rCarlsbad, California 92010, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jinghua","family":"Yu","sequence":"additional","affiliation":[{"name":"Isis Pharmaceuticals, 2855 Gazelle Court,\rCarlsbad, California 92010, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ali","family":"Jazayeri","sequence":"additional","affiliation":[{"name":"Isis Pharmaceuticals, 2855 Gazelle Court,\rCarlsbad, California 92010, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Pradeep S.","family":"Pallan","sequence":"additional","affiliation":[{"name":"Department of Biochemistry,\rSchool of Medicine, Vanderbilt University, 607 Light Hall, Nashville, Tennessee 37232, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Charles R","family":"Allerson","sequence":"additional","affiliation":[{"name":"Regulus Therapeutics, 3545 John Hopkins Ct., San Diego, California 92121, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Michael E.","family":"\u00d8stergaard","sequence":"additional","affiliation":[{"name":"Isis Pharmaceuticals, 2855 Gazelle Court,\rCarlsbad, California 92010, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fengwu","family":"Liu","sequence":"additional","affiliation":[{"name":"Laboratory of Medicinal Chemistry,\rRega Institute for Medical Research, Katholieke Universiteit, Minderbroedersstraat 10, 3000 Leuven, Belgium"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Piet","family":"Herdewijn","sequence":"additional","affiliation":[{"name":"Laboratory of Medicinal Chemistry,\rRega Institute for Medical Research, Katholieke Universiteit, Minderbroedersstraat 10, 3000 Leuven, Belgium"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Martin","family":"Egli","sequence":"additional","affiliation":[{"name":"Department of Biochemistry,\rSchool of Medicine, Vanderbilt University, 607 Light Hall, Nashville, Tennessee 37232, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Eric E.","family":"Swayze","sequence":"additional","affiliation":[{"name":"Isis Pharmaceuticals, 2855 Gazelle Court,\rCarlsbad, California 92010, United States"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"316","published-online":{"date-parts":[[2012,5,18]]},"reference":[{"key":"ref1\/cit1","doi-asserted-by":"crossref","first-page":"14514","DOI":"10.1016\/S0021-9258(19)85268-7","volume":"268","author":"Monia B. P.","year":"1993","journal-title":"J. Biol. Chem."},{"key":"ref2\/cit2","doi-asserted-by":"crossref","first-page":"314","DOI":"10.1126\/science.1857967","volume":"253","author":"Pieken W.","year":"1991","journal-title":"Science"},{"key":"ref3\/cit3","doi-asserted-by":"publisher","DOI":"10.1038\/nchembio.939"},{"key":"ref4\/cit4","doi-asserted-by":"crossref","first-page":"70","DOI":"10.1093\/nar\/gkn904","volume":"37","author":"Davis S.","year":"2009","journal-title":"Nucleic Acids Res."},{"key":"ref5\/cit5","doi-asserted-by":"crossref","first-page":"901","DOI":"10.1021\/jm049167j","volume":"48","author":"Allerson C. R.","year":"2005","journal-title":"J. Med. Chem."},{"key":"ref6\/cit6","doi-asserted-by":"crossref","first-page":"2284","DOI":"10.1002\/anie.201006519","volume":"50","author":"Manoharan M.","year":"2011","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref7\/cit7","doi-asserted-by":"crossref","first-page":"123","DOI":"10.1038\/nrd1955","volume":"5","author":"Ng E. W.","year":"2006","journal-title":"Nat. Rev. Drug Discovery"},{"key":"ref8\/cit8","doi-asserted-by":"crossref","first-page":"4001","DOI":"10.1021\/bi00230a027","volume":"30","author":"Williams D. M.","year":"1991","journal-title":"Biochemistry"},{"key":"ref9\/cit9","doi-asserted-by":"crossref","first-page":"831","DOI":"10.1021\/jm00059a007","volume":"36","author":"Kawasaki A. M.","year":"1993","journal-title":"J. Med. Chem."},{"key":"ref10\/cit10","doi-asserted-by":"crossref","first-page":"365","DOI":"10.1016\/0014-5793(85)80334-3","volume":"182","author":"Fazakerley G. V.","year":"1985","journal-title":"FEBS Lett."},{"key":"ref11\/cit11","doi-asserted-by":"crossref","first-page":"3482","DOI":"10.1093\/nar\/gkq1270","volume":"39","author":"Pallan P. S.","year":"2011","journal-title":"Nucleic Acids Res."},{"key":"ref12\/cit12","doi-asserted-by":"crossref","first-page":"12976","DOI":"10.1021\/ja982325+","volume":"120","author":"Damha M. J.","year":"1998","journal-title":"J. Am. Chem. Soc."},{"key":"ref13\/cit13","doi-asserted-by":"crossref","first-page":"3625","DOI":"10.1093\/nar\/28.18.3625","volume":"28","author":"Wilds C. J.","year":"2000","journal-title":"Nucleic Acids Res."},{"key":"ref14\/cit14","doi-asserted-by":"crossref","first-page":"2473","DOI":"10.1093\/nar\/26.10.2473","volume":"26","author":"Berger I.","year":"1998","journal-title":"Nucleic Acids Res."},{"key":"ref15\/cit15","doi-asserted-by":"crossref","first-page":"3525","DOI":"10.1021\/bi992792j","volume":"39","author":"Minasov G.","year":"2000","journal-title":"Biochemistry"},{"key":"ref16\/cit16","doi-asserted-by":"crossref","first-page":"728","DOI":"10.1021\/ja109817p","volume":"133","author":"Anzahaee M. Y.","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"ref17\/cit17","doi-asserted-by":"crossref","first-page":"16642","DOI":"10.1021\/ja207086x","volume":"133","author":"Egli M.","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"ref18\/cit18","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1021\/bi201810r","volume":"51","author":"Pallan P. S.","year":"2011","journal-title":"Biochemistry"},{"key":"ref19\/cit19","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/cbdv.200900185","volume":"7","author":"Herdewijn P.","year":"2010","journal-title":"Chem. Biodiversity"},{"key":"ref20\/cit20","doi-asserted-by":"crossref","first-page":"719","DOI":"10.1016\/S1074-5521(00)00017-X","volume":"7","author":"Lescrinier E.","year":"2000","journal-title":"Chem. Biol."},{"key":"ref21\/cit21","doi-asserted-by":"crossref","first-page":"4941","DOI":"10.1093\/nar\/29.24.4941","volume":"29","author":"Verbeure B.","year":"2001","journal-title":"Nucleic Acids Res."},{"key":"ref22\/cit22","doi-asserted-by":"crossref","first-page":"1591","DOI":"10.1016\/S0960-894X(01)00270-0","volume":"11","author":"Herdewijn P.","year":"2001","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref23\/cit23","doi-asserted-by":"crossref","first-page":"8595","DOI":"10.1021\/ja000018+","volume":"122","author":"Wang J.","year":"2000","journal-title":"J. Am. Chem. Soc."},{"key":"ref24\/cit24","doi-asserted-by":"crossref","first-page":"736","DOI":"10.1021\/jm991171l","volume":"43","author":"Wang J.","year":"2000","journal-title":"J. Med. Chem."},{"key":"ref25\/cit25","doi-asserted-by":"crossref","first-page":"1979","DOI":"10.1021\/ja077313f","volume":"130","author":"Robeyns K.","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref26\/cit26","doi-asserted-by":"crossref","first-page":"1407","DOI":"10.1093\/nar\/gkm1132","volume":"36","author":"Robeyns K.","year":"2008","journal-title":"Nucleic Acids Res."},{"key":"ref27\/cit27","doi-asserted-by":"crossref","first-page":"2","DOI":"10.4161\/adna.1.1.10952","volume":"1","author":"Robeyns K.","year":"2010","journal-title":"Artif. DNA: PNA & XNA"},{"key":"ref28\/cit28","doi-asserted-by":"crossref","first-page":"9340","DOI":"10.1021\/ja067047q","volume":"129","author":"Nauwelaerts K.","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref29\/cit29","doi-asserted-by":"crossref","first-page":"14942","DOI":"10.1021\/ja105875e","volume":"132","author":"Seth P. P.","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref30\/cit30","doi-asserted-by":"crossref","first-page":"1494","DOI":"10.1111\/j.1742-4658.2009.06908.x","volume":"276","author":"Cerritelli S. M.","year":"2009","journal-title":"FEBS J."},{"key":"ref31\/cit31","doi-asserted-by":"crossref","first-page":"17181","DOI":"10.1074\/jbc.M311683200","volume":"279","author":"Wu H.","year":"2004","journal-title":"J. Biol. Chem."},{"key":"ref32\/cit32","doi-asserted-by":"crossref","first-page":"1437","DOI":"10.1126\/science.1102513","volume":"305","author":"Liu J.","year":"2004","journal-title":"Science"},{"key":"ref33\/cit33","doi-asserted-by":"crossref","first-page":"993","DOI":"10.1081\/NCN-200060326","volume":"24","author":"Gu P.","year":"2005","journal-title":"Nucleosides, Nucleotides Nucleic Acids"},{"key":"ref34\/cit34","doi-asserted-by":"crossref","first-page":"4499","DOI":"10.1021\/jo0300946","volume":"68","author":"Wang J.","year":"2003","journal-title":"J. Org. Chem."},{"key":"ref35\/cit35","doi-asserted-by":"crossref","first-page":"8478","DOI":"10.1021\/jo015924z","volume":"66","author":"Wang J.","year":"2001","journal-title":"J. Org. Chem."},{"key":"ref36\/cit36","doi-asserted-by":"crossref","first-page":"3621","DOI":"10.1016\/j.tetlet.2007.03.031","volume":"48","author":"Horvath A.","year":"2007","journal-title":"Tetrahedron Lett."},{"key":"ref37\/cit37","doi-asserted-by":"crossref","first-page":"3280","DOI":"10.1021\/jo00116a008","volume":"60","author":"Jung M. E.","year":"1995","journal-title":"J. Org. Chem."},{"key":"ref38\/cit38","doi-asserted-by":"crossref","first-page":"169","DOI":"10.1016\/S0040-4039(99)02046-8","volume":"41","author":"Xia J.","year":"2000","journal-title":"Tetrahedron Lett."},{"key":"ref39\/cit39","doi-asserted-by":"crossref","first-page":"1569","DOI":"10.1021\/jo902560f","volume":"75","author":"Seth P. P.","year":"2010","journal-title":"J. Org. Chem."},{"key":"ref40\/cit40","doi-asserted-by":"crossref","first-page":"2480","DOI":"10.1021\/jo00406a041","volume":"43","author":"Mancuso A. J.","year":"1978","journal-title":"J. Org. Chem."},{"key":"ref41\/cit41","doi-asserted-by":"crossref","first-page":"849","DOI":"10.1081\/NCN-120016572","volume":"21","author":"Takamatsu S.","year":"2002","journal-title":"Nucleosides, Nucleotides Nucleic Acids"},{"key":"ref42\/cit42","doi-asserted-by":"crossref","first-page":"2080","DOI":"10.1016\/j.tet.2007.12.049","volume":"64","author":"Bechor Y.","year":"2008","journal-title":"Tetrahedron"},{"key":"ref43\/cit43","doi-asserted-by":"crossref","first-page":"901","DOI":"10.3390\/10080901","volume":"10","author":"Takahashi H.","year":"2005","journal-title":"Molecules"},{"key":"ref45\/cit45","doi-asserted-by":"crossref","first-page":"2226","DOI":"10.1021\/ja00475a040","volume":"100","author":"Luche J. L.","year":"1978","journal-title":"J. Am. Chem. Soc."},{"key":"ref46\/cit46","doi-asserted-by":"crossref","first-page":"1079","DOI":"10.1080\/15257779908041652","volume":"18","author":"Busson R.","year":"1999","journal-title":"Nucleosides, Nucleotides Nucleic Acids"},{"key":"ref47\/cit47","doi-asserted-by":"crossref","first-page":"296","DOI":"10.1016\/j.bmcl.2011.11.012","volume":"22","author":"Seth P. P.","year":"2012","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref48\/cit48","doi-asserted-by":"crossref","first-page":"1122","DOI":"10.1016\/j.bmcl.2010.12.119","volume":"21","author":"Seth P. P.","year":"2011","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref49\/cit49","doi-asserted-by":"crossref","first-page":"4690","DOI":"10.1016\/j.bmcl.2011.06.104","volume":"21","author":"Seth P. P.","year":"2011","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref50\/cit50","doi-asserted-by":"crossref","first-page":"8309","DOI":"10.1021\/jm101207e","volume":"53","author":"Seth P. P.","year":"2010","journal-title":"J. Med. Chem."},{"key":"ref51\/cit51","doi-asserted-by":"crossref","first-page":"4886","DOI":"10.1021\/ja710342q","volume":"130","author":"AbdurRahman S. M.","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref52\/cit52","doi-asserted-by":"crossref","first-page":"5272","DOI":"10.1039\/c1ob05469d","volume":"9","author":"Mori K.","year":"2011","journal-title":"Org. Biomol. Chem."},{"key":"ref53\/cit53","doi-asserted-by":"crossref","first-page":"5401","DOI":"10.1016\/S0040-4039(98)01084-3","volume":"39","author":"Obika S.","year":"1998","journal-title":"Tetrahedron Lett."},{"key":"ref54\/cit54","doi-asserted-by":"crossref","first-page":"5974","DOI":"10.1021\/ja012288d","volume":"124","author":"Petersen M.","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref55\/cit55","doi-asserted-by":"crossref","first-page":"14240","DOI":"10.1073\/pnas.96.25.14240","volume":"96","author":"Teplova M.","year":"1999","journal-title":"Proc. Nat. Acad. Sci. U.S.A.."},{"key":"ref56\/cit56","doi-asserted-by":"crossref","first-page":"10","DOI":"10.1021\/jm801294h","volume":"52","author":"Seth P. P.","year":"2009","journal-title":"J. Med. Chem."},{"key":"ref57\/cit57","doi-asserted-by":"crossref","first-page":"1636","DOI":"10.1021\/jm9013295","volume":"53","author":"Prakash T. P.","year":"2010","journal-title":"J. Med. Chem."},{"key":"ref58\/cit58","doi-asserted-by":"crossref","first-page":"341","DOI":"10.1126\/science.1217622","volume":"336","author":"Pinheiro V. B.","year":"2012","journal-title":"Science"}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jo300594b","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,4,13]],"date-time":"2023-04-13T21:00:53Z","timestamp":1681419653000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/jo300594b"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,5,18]]},"references-count":57,"journal-issue":{"issue":"11","published-print":{"date-parts":[[2012,6,1]]}},"alternative-id":["10.1021\/jo300594b"],"URL":"https:\/\/doi.org\/10.1021\/jo300594b","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2012,5,18]]}}}