1,2-Diol and hydrazide phosphoramidites for solid-phase synthesis and chemoselective ligation of 2'-modified oligonucleotides.
The preparation of two novel 2'-O-alkyl phosphoramidites bearing 1,2-diol and hydrazide functions for a chemoselective ligation is described. The former amidite was used to obtain 2'-modified oligodeoxyribonucleotides, which can be later oxidised by NaIO4 to generate 2'-aldehyde oligonucleotides. These were successfully conjugated to acceptor molecules. The latter amidite also showed good coupling yields, but the hydrazide function was demonstrated to be labile under basic deprotection conditions.
Zubin
Eugeny M
EM
Chemistry Department and A.N. Belozersky Institute of Physico-Chemical Biology, M.V. Lomonosov Moscow State University, Moscow, Russia.
Stetsenko
Dmitry A
DA
Oretskaya
Tatiana S
TS
Gait
Michael J
MJ
D000577:Amides; D006834:Hydrazines; D007202:Indicators and Reagents; D015394:Molecular Structure; D009843:Oligoribonucleotides / Q000138:chemical synthesis*; D010756:Phosphoric Acids
D000577:Amides; D006834:Hydrazines; D007202:Indicators and Reagents; D009843:Oligoribonucleotides; D010756:Phosphoric Acids; C029424:hydrazine; C011067:phosphoramidic acid