{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,7,30]],"date-time":"2025-07-30T09:45:05Z","timestamp":1753868705761,"version":"3.41.2"},"reference-count":31,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2020,12,8]],"date-time":"2020-12-08T00:00:00Z","timestamp":1607385600000},"content-version":"vor","delay-in-days":7,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100002341","name":"Academy of Finland","doi-asserted-by":"publisher","award":["308931"],"award-info":[{"award-number":["308931"]}],"id":[{"id":"10.13039\/501100002341","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["currentprotocols.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["CP Nucleic Acid Chemistry"],"published-print":{"date-parts":[[2020,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A detailed protocol for preparation 3\u2032\u2010glycoconjugated oligonucleotides is described based on one\u2010pot immobilization of 4,4\u2032\u2010dimethoxytrityl\u2010protected carbohydrates to a solid support followed by on\u2010support peracetylation and automated oligonucleotide assembly. Compared to an appropriate building block approach and post\u2010synthetic manipulation of oligonucleotides, this protocol may simplify the synthesis scheme and increase overall yield of the conjugates. Furthermore, the immobilization to a solid support typically increases the stability of reactants, enabling prolonged storage, and makes subsequent processing convenient. Automated assembly on these carbohydrate\u2010modified supports using conventional phosphoramidite chemistry produces 3\u2032\u2010glycoconjugated oligonucleotides in relatively high yield and purity. \u00a9 2020 Wiley Periodicals LLC.<\/jats:p><jats:p><jats:bold>Basic Protocol 1<\/jats:bold>: Synthesis of 1\u2010<jats:italic>O<\/jats:italic>\u2010<jats:italic>tert<\/jats:italic>\u2010butyldimethylsilyl\u20106\u2010<jats:italic>O<\/jats:italic>\u2010(4,4\u2032\u2010dimethoxytrityl)\u2010\u03b2\u2010<jats:sc>D<\/jats:sc>\u2010glucose<\/jats:p><jats:p><jats:bold>Basic Protocol 2<\/jats:bold>: Synthesis of 6\u2010<jats:italic>O<\/jats:italic>\u2010dimethoxytrityl\u20102,3,1\u2032,3\u2032,4\u2032,6\u2032\u2010hexa\u2010<jats:italic>O<\/jats:italic>\u2010benzoylsucrose<\/jats:p><jats:p><jats:bold>Basic Protocol 3<\/jats:bold>: Synthesis of 6\u2033\u2010<jats:italic>O<\/jats:italic>\u2010dimethoxytrityl\u2010<jats:italic>N<\/jats:italic>\u2010trifluoroacetyl\u2010protected aminoglycosides<\/jats:p><jats:p><jats:bold>Basic Protocol 4<\/jats:bold>: Synthesis of 3\u2010<jats:italic>O<\/jats:italic>\u2010dimethoxytrityl\u2010propyl \u03b2\u2010<jats:sc>D<\/jats:sc>\u2010galactopyranoside<\/jats:p><jats:p><jats:bold>Basic Protocol 5<\/jats:bold>: Synthesis of trivalent <jats:italic>N<\/jats:italic>\u2010acetyl galactosamine cluster<\/jats:p><jats:p><jats:bold>Basic Protocol 6<\/jats:bold>: Synthesis of carbohydrate monosuccinates and their immobilization to a solid support<\/jats:p><jats:p><jats:bold>Basic Protocol 7<\/jats:bold>: Oligonucleotide synthesis using immobilized carbohydrates<\/jats:p>","DOI":"10.1002\/cpnc.122","type":"journal-article","created":{"date-parts":[[2020,12,9]],"date-time":"2020-12-09T20:52:42Z","timestamp":1607547162000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Immobilized Carbohydrates for Preparation of 3\u2032\u2010Glycoconjugated Oligonucleotides"],"prefix":"10.1002","volume":"83","author":[{"given":"Tommi","family":"\u00d6sterlund","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Turku  Turku Finland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Aapo","family":"Aho","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Turku  Turku Finland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Antti","family":"\u00c4\u00e4rel\u00e4","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Turku  Turku Finland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ville","family":"T\u00e4htinen","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Turku  Turku Finland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Heidi","family":"Korhonen","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Turku  Turku Finland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Pasi","family":"Virta","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Turku  Turku Finland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2020,12,8]]},"reference":[{"key":"e_1_2_11_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar100113q"},{"key":"e_1_2_11_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.bioconjchem.8b00761"},{"key":"e_1_2_11_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2ob25207d"},{"key":"e_1_2_11_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol006175v"},{"key":"e_1_2_11_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc0256244"},{"key":"e_1_2_11_7_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules22050760"},{"key":"e_1_2_11_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.bioconjchem.8b00317"},{"key":"e_1_2_11_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.bioconjchem.5b00477"},{"key":"e_1_2_11_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc900529g"},{"key":"e_1_2_11_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc800260y"},{"key":"e_1_2_11_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo048984o"},{"key":"e_1_2_11_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc049955n"},{"key":"e_1_2_11_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc7004279"},{"key":"e_1_2_11_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc200097g"},{"key":"e_1_2_11_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc800221p"},{"key":"e_1_2_11_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc100268w"},{"key":"e_1_2_11_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc200101r"},{"key":"e_1_2_11_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/0008-6215(94)80046-4"},{"key":"e_1_2_11_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.10.034"},{"key":"e_1_2_11_21_1","first-page":"A.3D.1","article-title":"Thin\u2010layer 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