acetylated and methylated β-cyclodextrins as viable soluble supports for the synthesis of short 2′-oligodeoxyribo-nucleotides in solution乙酰化和甲基化β-cyclodextrins可行的合成可溶性支持短2u2032-oligodeoxyribo-nucleotides在解决方案.pdfVIP

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acetylated and methylated β-cyclodextrins as viable soluble supports for the synthesis of short 2′-oligodeoxyribo-nucleotides in solution乙酰化和甲基化β-cyclodextrins可行的合成可溶性支持短2u2032-oligodeoxyribo-nucleotides在解决方案.pdf

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acetylated and methylated β-cyclodextrins as viable soluble supports for the synthesis of short 2′-oligodeoxyribo-nucleotides in solution乙酰化和甲基化β-cyclodextrins可行的合成可溶性支持短2u2032-oligodeoxyribo-nucleotides在解决方案

Molecules 2012, 17, 12102-12120; doi:10.3390/molecules171012102 OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Acetylated and Methylated β-Cyclodextrins as Viable Soluble Supports for the Synthesis of Short 2′-Oligodeoxyribo-nucleotides in Solution Alejandro Gimenez Molina, Vyacheslav Kungurtsev, Pasi Virta and Harri Lönnberg * Department of Chemistry, University of Turku, FIN-20014 Turku, Finland; E-Mails: algimo@utu.fi (A.G.M.); vyakun@utu.fi (V.K.); pamavi@utu.fi (P.V.) * Author to whom correspondence should be addressed; E-Mail: harlon@utu.fi; Tel.: +358-2-333-6770; Fax: +358-2-333-6700. Received: 12 September 2012; in revised form: 12 October 2012 / Accepted: 12 October 2012 / Published: 16 October 2012 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