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Title
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Synthesis of 3'-deoxy-3'-c-hydroxymethyl-aldopentopyranosyl nucleosides and their incorporation in oligonucleotides : part 2, 1
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Author
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Abstract
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| The synthesis of 3'-deoxy-3'-C-hydroxymethyl-aldopentopyranosyl nucleosides using an intramolecular radical C-C bond formation reaction is described. This method gives good results for the synthesis of thymine and adenine nucleosides, but not for cytosine and guanine nucleosides. Dependent on the configuration (beta-D-erythro or alpha-L-threo), the conformation of the adenine nucleosides is clearly different (axial base moiety for alpha-D-erythro and equatorial adenine base for alpha-L-threo nucleosides) which could be explained by the gauche effect. Oligonucleotides built up of 2',3'-dideoxy-3'-C-hydroxymethyl-alpha-L-threo-pentopyranosyl adenine are able to form duplexes with oligothymidylate although with less stability than natural dsDNA. |
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Language
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English
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Source (journal)
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Tetrahedron. - Oxford, 1957, currens
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Publication
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Oxford
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1995
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ISSN
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0040-4020
[print]
1464-5416
[online]
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DOI
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10.1016/0040-4020(95)00777-6
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Volume/pages
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51
:45
(1995)
, p. 12319-12336
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ISI
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A1995TD21800014
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Full text (Publisher's DOI)
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Full text (publisher's version - intranet only)
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