{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,8]],"date-time":"2026-06-08T15:58:13Z","timestamp":1780934293396,"version":"3.54.1"},"reference-count":60,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2024,1,17]],"date-time":"2024-01-17T00:00:00Z","timestamp":1705449600000},"content-version":"vor","delay-in-days":16,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2024,1,1]],"date-time":"2024-01-01T00:00:00Z","timestamp":1704067200000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Current Protocols"],"published-print":{"date-parts":[[2024,1]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    The integration of fluorine atoms into biologically active organic compounds has proved to be a vital technique in small molecule drugs. This technique can substantially enhance crucial properties, including metabolic stability, lipophilicity, and bioavailability, often with a mere addition of a single fluorine atom or a trifluoromethyl group. Over the past few decades, this concept has also been applied in nucleic acid chemistry. A commonly employed 2\u2032\u2010OH substitution is the introduction of a 2\u2032\u2010deoxy\u20102\u2032\u2010fluoro (2\u2032\u2010F) group. The strong electronegativity of fluorine prompts the modified siRNA to readily adopt a C3\u2032\u2010\n                    <jats:italic>endo<\/jats:italic>\n                    conformation, resulting in significant advantages in terms of binding affinity. To enrich the toolbox of chemical modification of oligonucleotides, the replacement of the 2\u2032\u2010OH with the 2\u2032\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010trifluoromethyl group has been developed in RNA analog synthesis. Oligodeoxynucleotides containing the 2\u2032\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010trifluoromethyl group can greatly increase the thermal stability of DNA\/RNA duplexes depending on the position and amount of the modification. Moreover, 2\u2032\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010trifluoromethylated oligodeoxynucleotide also exhibited a slightly higher resistance to snake venom phosphodiesterase than the unmodified oligodeoxynucleotide. The 2\u2032\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010trifluoromethylated oligonucleotides can emerge as a label to study RNA structure and function as well, or to develop DNA\/RNA\u2010based diagnostics. Hence, it is necessary to report an effective method for the synthesis, deprotection, purification, and characterization of oligonucleotides bearing a 2\u2032\n                    <jats:italic>\u2010O<\/jats:italic>\n                    \u2010trifluoromethyl group. \u00a9 2024 Wiley Periodicals LLC.\n                  <\/jats:p>\n                  <jats:p>\n                    <jats:bold>Basic Protocol 1<\/jats:bold>\n                    : Preparation of 6\u2010\n                    <jats:italic>N<\/jats:italic>\n                    \u2010benzoyl\u20105\u2032\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010dimethoxytrityl\u20102\u2032\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010trifluoromethyl adenosine 3\u2032\u2010(2\u2010cyanoethyl\n                    <jats:italic>N,N<\/jats:italic>\n                    \u2010diisopropyl)phosphoramidite\n                  <\/jats:p>\n                  <jats:p>\n                    <jats:bold>Basic Protocol 2<\/jats:bold>\n                    : Preparation of 4\u2010\n                    <jats:italic>N<\/jats:italic>\n                    \u2010acetyl\u20105\u2032\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010dimethoxytrityl\u20102\u2032\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010trifluoromethyl cytidine 3\u2032\u2010(2\u2010cyanoethyl\n                    <jats:italic>N,N<\/jats:italic>\n                    \u2010diisopropyl)phosphoramidite\n                  <\/jats:p>\n                  <jats:p>\n                    <jats:bold>Basic Protocol 3<\/jats:bold>\n                    : Preparation of 2\u2010\n                    <jats:italic>N<\/jats:italic>\n                    \u2010isobutyryl\u20105\u2032\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010dimethoxytrityl\u20102\u2032\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010trifluoromethyl guanine 3\u2032\u2010(2\u2010cyanoethyl\n                    <jats:italic>N,N<\/jats:italic>\n                    \u2010diisopropyl)phosphoramidite\n                  <\/jats:p>\n                  <jats:p>\n                    <jats:bold>Basic Protocol 4<\/jats:bold>\n                    : Preparation of 5\u2032\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010dimethoxytrityl\u20102\u2032\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u20102\u2010trifluoromethyl uridine 3\u2032\u2010(2\u2010cyanoethyl\n                    <jats:italic>N,N<\/jats:italic>\n                    \u2010diisopropyl) phosphoramidite\n                  <\/jats:p>\n                  <jats:p>\n                    <jats:bold>Basic Protocol 5<\/jats:bold>\n                    : Solid\u2010phase synthesis of 2\u2032\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010trifluoromethylated RNA analogs\n                  <\/jats:p>\n                  <jats:p>\n                    <jats:bold>Basic Protocol 6<\/jats:bold>\n                    : Deprotection and purification of 2\u2032\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010trifluoromethyl\u2010RNAs\n                  <\/jats:p>","DOI":"10.1002\/cpz1.956","type":"journal-article","created":{"date-parts":[[2024,1,17]],"date-time":"2024-01-17T05:03:16Z","timestamp":1705467796000},"source":"Crossref","is-referenced-by-count":0,"title":["Synthesis of Nucleotides Bearing the 2\u2032\u2010\n                    <i>O<\/i>\n                    \u2010Trifluoromethyl Group and Their Application in RNA Analogs Preparation"],"prefix":"10.1002","volume":"4","author":[{"given":"Xuan","family":"Chen","sequence":"first","affiliation":[{"name":"Sirnaomics Ltd.  Suzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Long","family":"Xie","sequence":"additional","affiliation":[{"name":"Sirnaomics Ltd.  Suzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chenglong","family":"Zhang","sequence":"additional","affiliation":[{"name":"Sirnaomics Ltd.  Suzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shen","family":"Tian","sequence":"additional","affiliation":[{"name":"Sirnaomics Ltd.  Suzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zeyu","family":"Tang","sequence":"additional","affiliation":[{"name":"Sirnaomics Ltd.  Suzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ming","family":"Xiang","sequence":"additional","affiliation":[{"name":"Sirnaomics Ltd.  Suzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Weiwei","family":"Tian","sequence":"additional","affiliation":[{"name":"Sirnaomics Ltd.  Suzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Patrick","family":"Lu","sequence":"additional","affiliation":[{"name":"Sirnaomics Ltd.  Suzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xianbin","family":"Yang","sequence":"additional","affiliation":[{"name":"Sirnaomics Ltd.  Suzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,1,17]]},"reference":[{"key":"e_1_2_10_2_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkw725"},{"key":"e_1_2_10_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2005.07.025"},{"key":"e_1_2_10_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi0343774"},{"key":"e_1_2_10_5_1","doi-asserted-by":"publisher","DOI":"10.3389\/fphar.2019.00444"},{"key":"e_1_2_10_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/cpnc.118"},{"key":"e_1_2_10_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01485a036"},{"key":"e_1_2_10_8_1","doi-asserted-by":"publisher","DOI":"10.1172\/JCI33483"},{"key":"e_1_2_10_9_1","doi-asserted-by":"publisher","DOI":"10.1128\/aac.49.1.249\u2010255.2005"},{"key":"e_1_2_10_10_1","doi-asserted-by":"publisher","DOI":"10.3390\/app2020245"},{"key":"e_1_2_10_11_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gky268"},{"key":"e_1_2_10_12_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkl033"},{"key":"e_1_2_10_13_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkad067"},{"key":"e_1_2_10_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi050574m"},{"key":"e_1_2_10_15_1","doi-asserted-by":"publisher","DOI":"10.1007\/s40259\u2010022\u201000549\u20103"},{"key":"e_1_2_10_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.5b00258"},{"key":"e_1_2_10_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm800219f"},{"key":"e_1_2_10_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr00002a004"},{"key":"e_1_2_10_19_1","volume-title":"Substituent constants for correlation analysis in chemistry and biology","author":"Hansch C. H.","year":"1979"},{"key":"e_1_2_10_20_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC04520A"},{"key":"e_1_2_10_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja965433"},{"key":"e_1_2_10_22_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41392\u2010020\u20100207\u2010x"},{"key":"e_1_2_10_23_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/15.15.6131"},{"key":"e_1_2_10_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/cpz1.837"},{"key":"e_1_2_10_25_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkz140"},{"key":"e_1_2_10_26_1","doi-asserted-by":"publisher","DOI":"10.1039\/A708608C"},{"key":"e_1_2_10_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm00059a007"},{"key":"e_1_2_10_28_1","doi-asserted-by":"publisher","DOI":"10.1158\/0008\u20105472.Can\u201016\u20101571"},{"key":"e_1_2_10_29_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200900974"},{"key":"e_1_2_10_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2009.06.045"},{"key":"e_1_2_10_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr60274a001"},{"key":"e_1_2_10_32_1","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.4.13"},{"key":"e_1_2_10_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201006519"},{"key":"e_1_2_10_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm1013693"},{"key":"e_1_2_10_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar900292q"},{"key":"e_1_2_10_36_1","doi-asserted-by":"publisher","DOI":"10.3390\/pharmaceutics14020260"},{"key":"e_1_2_10_37_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/26.22.5067"},{"key":"e_1_2_10_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2007.09.019"},{"key":"e_1_2_10_39_1","doi-asserted-by":"publisher","DOI":"10.1039\/C29690000077"},{"key":"e_1_2_10_40_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkq1270"},{"key":"e_1_2_10_41_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4RA10986D"},{"key":"e_1_2_10_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.7b01147"},{"key":"e_1_2_10_43_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201204946"},{"key":"e_1_2_10_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsmedchemlett.1c00072"},{"key":"e_1_2_10_45_1","doi-asserted-by":"publisher","DOI":"10.1016\/0005\u20102787(71)90144\u20104"},{"key":"e_1_2_10_46_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ebiom.2018.11.045"},{"key":"e_1_2_10_47_1","doi-asserted-by":"publisher","DOI":"10.1111\/cbdd.12993"},{"key":"e_1_2_10_48_1","doi-asserted-by":"publisher","DOI":"10.1080\/10426507.2012.745079"},{"key":"e_1_2_10_49_1","first-page":"65","volume-title":"Progress in Medicinal Chemistry","author":"Swallow S.","year":"2015"},{"key":"e_1_2_10_50_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201603697"},{"key":"e_1_2_10_51_1","unstructured":"Vagle K. Vargeese C. &Chen T.(2005).Fluoroalkoxy nucleosides nucleotides and polynucleotides. In: Google Patents."},{"key":"e_1_2_10_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi0485732"},{"key":"e_1_2_10_53_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr4002879"},{"key":"e_1_2_10_54_1","doi-asserted-by":"publisher","DOI":"10.1055\/s\u20102004\u2010815972"},{"key":"e_1_2_10_55_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biotechadv.2019.04.012"},{"key":"e_1_2_10_56_1","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms4459"},{"key":"e_1_2_10_57_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b01510"},{"key":"e_1_2_10_58_1","doi-asserted-by":"publisher","DOI":"10.1002\/cpnc.40"},{"key":"e_1_2_10_59_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC05722A"},{"key":"e_1_2_10_60_1","doi-asserted-by":"publisher","DOI":"10.1039\/B9NJ00618D"},{"key":"e_1_2_10_61_1","doi-asserted-by":"publisher","DOI":"10.1021\/cb300078e"}],"container-title":["Current Protocols"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/currentprotocols.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cpz1.956","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/currentprotocols.onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cpz1.956","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/currentprotocols.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cpz1.956","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,6,8]],"date-time":"2026-06-08T15:06:10Z","timestamp":1780931170000},"score":1,"resource":{"primary":{"URL":"https:\/\/currentprotocols.onlinelibrary.wiley.com\/doi\/10.1002\/cpz1.956"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,1]]},"references-count":60,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2024,1]]}},"alternative-id":["10.1002\/cpz1.956"],"URL":"https:\/\/doi.org\/10.1002\/cpz1.956","archive":["Portico"],"relation":{},"ISSN":["2691-1299","2691-1299"],"issn-type":[{"value":"2691-1299","type":"print"},{"value":"2691-1299","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,1]]},"article-number":"e956"}}