Synthesis of nucleic acid methylphosphonates via the 1-hydroxybenzotriazole phoaphotriester approach
- 1 January 1986
- journal article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 14 (5) , 2171-2185
- https://doi.org/10.1093/nar/14.5.2171
Abstract
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.Keywords
This publication has 12 references indexed in Scilit:
- Characterization of sequence-specific oligodeoxyribonucleoside methylphosphonates and their interaction with rabbit globin mRNABiochemistry, 1985
- Methylphosphonates as probes of protein-nucleic acid interactionsNucleic Acids Research, 1984
- Synthesis of phosphorothloate-contaming DNA fragments by a modified bydroxybenzotriazole phospbotriester approachNucleic Acids Research, 1984
- Polymer supported DNA synthesis using hydroxybenzotriazole activated pbosphotriester intermediatesNucleic Acids Research, 1984
- Synthesis of short RNA fragments by the benzotriazolyl phosphotriester approachNucleic Acids Research, 1983
- Some observations relating to the oximate ion promoted unblocking of oligonucleotide aryl estersNucleic Acids Research, 1981
- Biochemical and biological effects of nonionic nucleic acid methylphosphonatesBiochemistry, 1981
- Nonionic nucleic acid analogs. Synthesis and characterization of dideoxyribonucleoside methylphosphonatesBiochemistry, 1979
- Synthesis and enzymatic properties of deoxyribooligonucleotides containing methyl and phenylphosphonate linkagesNucleic Acids Research, 1979
- The synthesis of oligoribonucleotides—IITetrahedron, 1967