The precursor strategy: terminus methoxyoxalamido modifiers for single and multiple functionalization of oligodeoxyribonucleotides.
Synthesis of new terminus modifiers, bearing, along with a phosphoramidite moiety, one, two or four methoxyoxalamido (MOX) precursor groups, is described. These modifiers are introduced onto the 5'-end of a synthetic oligodeoxyribonucleotide as the last step of an automated synthesis to form the MOX precursor oligonucleotide. The MOX groups are then post-synthetically derivatized with an appropriate primary amine to construct a 5'-modified oligonucleotide. The efficiency and simplicity of the novel modifying strategy were demonstrated in the synthesis of a number of 5'-functionalized oligonucleotides.
Fidelity Systems Inc., 7961 Cessna Avenue, Gaithersburg, MD 20879, USA. npolouchine@fidelitysystems.com
N N
NN
Polushin
D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D009690:Nucleic Acid Conformation; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds; D010072:Oxamic Acid; D018629:Spectrometry, Mass, Secondary Ion; D013941:Thymine
D007202:Indicators and Reagents; D009838:Oligodeoxyribonucleotides; D009943:Organophosphorus Compounds; D013941:Thymine; D010072:Oxamic Acid