Versatile strategy for oligonucleotide derivatization. Introduction of lanthanide(III) chelates to oligonucleotides.
[reaction: see text] Novel nucleosidic phosphoramidite blocks were synthesized by a Mitsunobu reaction between 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine and a primary alcohol containing a conjugate group in its structure (a protected functional group, an organic dye, or a precursor of a lanthanide(III) chelate) followed by phosphitylation. They were used in machine-assisted DNA synthesis in the standard manner. A slightly modified deprotection procedure was used for the preparation of oligonucleotide conjugates tethered to lanthanide(III) chelates. For the latter application one non-nucleosidic block was also synthesized.
Hovinen
J
J
PerkinElmer Life Sciences, Wallac Oy, P.O. Box 10, FIN-20101 Turku, Finland. jari.hovinen@perkinelmer.com
Hakala
H
H
D000438:Alcohols / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis*; D002614:Chelating Agents / Q000737:chemistry*; D007202:Indicators and Reagents; D008674:Metals, Rare Earth / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis*
D000438:Alcohols; D000577:Amides; D002614:Chelating Agents; D007202:Indicators and Reagents; D008674:Metals, Rare Earth; D009841:Oligonucleotides; D009943:Organophosphorus Compounds