title: Acetylated and methylated β-cyclodextrins as viable soluble supports for the synthesis of short 2′-oligodeoxyribo-nucleotides in solution.
abstract: Novel soluble supports for oligonucleotide synthesis 11a-c have been prepared by immobilizing a 5′-O-protected 3′-O-(hex-5-ynoyl)thymidine (6 or 7) to peracetylated or permethylated 6-deoxy-6-azido-β-cyclodextrins 10a or 10b by Cu(I)-promoted 1,3-dipolar cycloaddition. The applicability of the supports to oligonucleotide synthesis by the phosphoramidite strategy has been demonstrated by assembling a 3′-TTT-5′ trimer from commercially available 5′-O-(4,4′-dimethoxytrityl)thymidine 3′-phosphoramidite. To simplify the coupling cycle, the 5′-O-(4,4′-dimethoxytrityl) protecting group has been replaced with an acetal that upon acidolytic removal yields volatile products. For this purpose, 5′-O-(1-methoxy-1-methylethyl)-protected 3′-(2-cyanoethyl-N,N-diisopropyl-phosphoramidite)s of thymidine (5a), N⁴-benzoyl-2′-deoxycytidine (5b) and N⁶-benzoyl-2′-deoxyadenosine (5c) have been synthesized and utilized in synthesis of a pentameric oligonucleotide 3′-TTCAT-5′ on the permethylated cyclodextrin support 11c.
authors.affiliation: Department of Chemistry, University of Turku, FIN-20014 Turku, Finland.
authors.forename: Alejandro Gimenez
authors.initials: AG
authors.lastname: Molina
authors.forename: Vyacheslav
authors.initials: V
authors.lastname: Kungurtsev
authors.forename: Pasi
authors.initials: P
authors.lastname: Virta
authors.forename: Harri
authors.initials: H
authors.lastname: Lönnberg
mesh_terms: D000107:Acetylation; D002851:Chromatography, High Pressure Liquid; D008745:Methylation; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis*; D012996:Solutions / Q000737:chemistry*; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D009838:Oligodeoxyribonucleotides; D012996:Solutions; D047392:beta-Cyclodextrins