7-Deaza-2′-Deoxyxanthosine: Nucleobase Protection and Base Pairing of Oligonucleotides

Oligonucleotides containing 7-deaza-2′-deoxyxanthosine (1) and 2′-deoxyxanthosine (2) were prepared. The 2-(4-nitrophenyl)ethyl group is applicable for 7-deazaxanthine protection that is removed with DBU by β-elimination, while the deprotection of the allyl residue with Pd (0) catalyst failed. Contr...

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Bibliographic Details
Published in:Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2007-01, Vol.26 (6-7), p.737-741
Main Authors: Shaikh, Khalil I., Leonard, Peter, Seela, Frank
Format: Article
Language:English
Subjects:
2′-Deoxyxanthosine
7-Deaza-2′-deoxyxanthosine
Base Pairing
Deoxyribonucleosides - chemistry
duplexes
Nucleosides - chemistry
oligonucleotides
Oligonucleotides - chemistry
Organophosphorus Compounds - chemical synthesis
Organophosphorus Compounds - chemistry
phosphoramidites
protecting groups
Transition Temperature
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Summary:Oligonucleotides containing 7-deaza-2′-deoxyxanthosine (1) and 2′-deoxyxanthosine (2) were prepared. The 2-(4-nitrophenyl)ethyl group is applicable for 7-deazaxanthine protection that is removed with DBU by β-elimination, while the deprotection of the allyl residue with Pd (0) catalyst failed. Contrarily, the allyl group was found to be an excellent protecting group for 2′-deoxyxanthosine (2). The base pairing of nucleosides 1 and 2 with the four canonical DNA constituents as well as with 3 within the 12-mer duplexes is studied.
ISSN:1525-7770
1532-2335
DOI:10.1080/15257770701490837