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Molecules 2012, 17(10), 12102-12120; doi:10.3390/molecules171012102
Article

Acetylated and Methylated β-Cyclodextrins as Viable Soluble Supports for the Synthesis of Short 2′-Oligodeoxyribo-nucleotides in Solution

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,
 and
*
Department of Chemistry, University of Turku, FIN-20014 Turku, Finland
* Author to whom correspondence should be addressed.
Received: 12 September 2012 / Revised: 12 October 2012 / Accepted: 12 October 2012 / Published: 16 October 2012
(This article belongs to the Special Issue Nucleic Acid Analogs)
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Abstract

Novel soluble supports for oligonucleotide synthesis 11ac 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.
Keywords: cyclodextrin; oligonucleotides; phosphoramidites; soluble support; synthesis cyclodextrin; oligonucleotides; phosphoramidites; soluble support; synthesis
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Molina, A.G.; Kungurtsev, V.; Virta, P.; Lönnberg, H. Acetylated and Methylated β-Cyclodextrins as Viable Soluble Supports for the Synthesis of Short 2′-Oligodeoxyribo-nucleotides in Solution. Molecules 2012, 17, 12102-12120.

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