Synthesis of nucleic acid methylphosphonates via the 1-hydroxybenzotriazole phosphotriester approach.
AUTOR(ES)
Marugg, J E
RESUMO
Dinucleoside methylphosphonates can easily be prepared starting from properly protected d-nucleosides and the bifunctional phosphorylating reagent methyl-O,O-bis(1-benzotriazolyl)phosphate. Separation of the diastereoisomers of 5'-DMTR-d-Ap(Me)T-3'-lev affords optically pure dinucleoside methylphosphonates which, after removal of the 3'-levulinoyl group, have been used for the synthesis of the two optically pure diastereoisomers of the hexamer d-CpGpAp(Me)TpCpG. Further, a one-pot procedure for the preparation of uridine-3',5'-cyclic methylphosphonate will be described. We also found that 3',5'-methylphosphonate linkages in RNA are not stable towards mild acid treatment.
ACESSO AO ARTIGO
http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=339650Documentos Relacionados
- Synthesis of phosphorothioate-containing DNA fragments by a modified hydroxybenzotriazole phosphotriester approach.
- Synthesis of riboguanosine pentaphosphate ppprGpp (Magic Spot II) via a phosphotriester approach.
- Synthesis of short RNA fragments by the benzotriazolyl phosphotriester approach.
- Synthesis of cyclic oligonucleotides by a modified phosphotriester approach.
- Use of a 1-hydroxybenzotriazole activated phosphorylating reagent towards the synthesis of short RNA fragments in solution.
