%0 Journal Article
%T Acetylated and Methylated ¦Â-Cyclodextrins as Viable Soluble Supports for the Synthesis of Short 2¡ä-Oligodeoxyribo-nucleotides in Solution
%A Alejandro Gimenez Molina
%A Vyacheslav Kungurtsev
%A Pasi Virta
%A Harri L£¿nnberg
%J Molecules
%D 2012
%I MDPI AG
%R 10.3390/molecules171012102
%X Novel soluble supports for oligonucleotide synthesis 11a¨Cc have been prepared by immobilizing a 5¡ä-O-protected 3¡ä-O-(hex-5-ynoyl)thymidine (6 or 7) to peracetylated or permethylated 6-deoxy-6-azido-¦Â-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¡ä-TTT-5¡ä trimer from commercially available 5¡ä-O-(4,4¡ä-dimethoxytrityl)thymidine 3¡ä-phosphoramidite. To simplify the coupling cycle, the 5¡ä-O-(4,4¡ä-dimethoxytrityl) protecting group has been replaced with an acetal that upon acidolytic removal yields volatile products. For this purpose, 5¡ä-O-(1-methoxy-1-methylethyl)-protected 3¡ä-(2-cyanoethyl-N,N-diisopropyl-phosphoramidite)s of thymidine (5a), N4-benzoyl-2¡ä-deoxycytidine (5b) and N6-benzoyl-2¡ä-deoxyadenosine (5c) have been synthesized and utilized in synthesis of a pentameric oligonucleotide 3¡ä-TTCAT-5¡ä on the permethylated cyclodextrin support 11c.
%K cyclodextrin
%K oligonucleotides
%K phosphoramidites
%K soluble support
%K synthesis
%U http://www.mdpi.com/1420-3049/17/10/12102