Solid-phase synthesis of backbone-modified DNA analogs by the boranophosphotriester method using new protecting groups for nucleobases.
Backbone-modified DNA analogs were synthesized in good yields by the boranophosphotriester method on a solid support. The oligodeoxyribonucleoside boranophosphates, protected with 2-(azidomethyl)benzoyl groups for nucleobases, were converted into DNA and its backbone-modified analogs via the corresponding H-phosphonate intermediates. A new protecting group for the O6 position of 2'-deoxyguanosine, 4-azidobenzyl (ABn) group, was also developed. The ABn group can be quickly removed by treatment with MePPh2 and H2O in the presence of 2-mercaptoethanol.
Department of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, Bioscience Building 702, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8562, Japan.
Toshihide
T
Kawanaka
Mamoru
M
Shimizu
Noriko
N
Shintani
Takeshi
T
Wada
D001880:Boranes / Q000737:chemistry*; D002626:Chemistry, Pharmaceutical / Q000379:methods; D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000737:chemistry* / Q000378:metabolism*; D015195:Drug Design; D004952:Esters / Q000737:chemistry; D006147:Guanine / Q000737:chemistry; D008623:Mercaptoethanol / Q000737:chemistry; D008956:Models, Chemical; D008967:Molecular Biology / Q000379:methods; D008968:Molecular Conformation; D009838:Oligodeoxyribonucleotides / Q000737:chemistry*; D009841:Oligonucleotides / Q000737:chemistry; D063065:Organophosphonates / Q000737:chemistry; D010710:Phosphates / Q000737:chemistry*
D001880:Boranes; D004952:Esters; D009838:Oligodeoxyribonucleotides; D009841:Oligonucleotides; D063065:Organophosphonates; D010710:Phosphates; C510710:boranophosphate; D006147:Guanine; D008623:Mercaptoethanol; D004247:DNA