Solid-Phase Synthesis of Oligo-2-Pyrimidinone-2′-Deoxyribonucleotides and Oligo-2-Pyrimidinone-2′-Deoxyriboside Methylphosphonates

A synthetic method was developed for the synthesis of oligodeoxyribonucleotides and oligodeoxyribonucleoside methylphosphonates comprised exclusively of the fluorescent 2-pyrimidinone base for the first time. The method utilized the solid-phase 2-cyanoethylphosphoramidite and methylphosphonamidite c...

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Bibliographic Details
Published in:Nucleic acids research 1996-07, Vol.24 (14), p.2652-2659
Main Authors: Zhou, Yuanzhong, Ts'o, Paul O. P.
Format: Article
Language:English
Subjects:
Molecular Structure
Oligodeoxyribonucleotides - chemical synthesis
Organophosphorus Compounds - chemical synthesis
Pyrimidinones - chemical synthesis
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Summary:A synthetic method was developed for the synthesis of oligodeoxyribonucleotides and oligodeoxyribonucleoside methylphosphonates comprised exclusively of the fluorescent 2-pyrimidinone base for the first time. The method utilized the solid-phase 2-cyanoethylphosphoramidite and methylphosphonamidite chemistry for internucleotide couplings and a base-labile oxalyl linkage to anchor the oligomers onto the CPG support. Cleavage of the oligomers from the support was effected by a short treatment of the support with 5% ammonium hydroxide in methanol at room temperature, without any degradation of the base-sensitive 2-pyrimidinone residues or the base-sensitive methylphosphonate backbone.
ISSN:0305-1048
1362-4962
DOI:10.1093/nar/24.14.2652