4,5-bis(ethoxycarbonyl)-[1,3]dioxolan-2-yl as a new orthoester-type protecting group for the 2'-hydroxyl function in the chemical synthesis of RNA.
We wish to report 4,5-bis(ethoxycarbonyl)-[1,3]dioxolan-2-yl as a new protecting for the 2'-hydroxyl function. Our cyclic orthoester-type group is compatible with the DMTr strategy for oligonucleotide synthesis. This group was introduced to the 2'-hydroxyl group of appropriately protected nucleoside derivatives in good yields under mild acidic conditions. Post-synthetic conversion of the moiety of this protecting group with an amine resulted in formation of a new amide moiety that is more stable to acid deprotection in aqueous solution, but it can still be easily removed by treatment with acids in organic solvents. In this article, we also describe the stability of not only the original and modified protecting groups but also internucleotidic phosphate linkages of protected RNA intermediates under deprotection conditions.
Karwowski
Boleslaw
B
Department of Life Science, Tokyo Institute of Technology, Japan and JST (Japan Science and Technology Corporation), Japan. karwowski@cea.fr
Seio
K
K
Sekine
M
M
D004148:Dioxolanes / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry*; D008956:Models, Chemical; D008967:Molecular Biology / Q000379:methods*; D009705:Nucleosides / Q000737:chemistry; D009841:Oligonucleotides / Q000138:chemical synthesis*; D009843:Oligoribonucleotides / Q000737:chemistry; D012313:RNA / Q000138:chemical synthesis* / Q000737:chemistry*
C506209:2-ethoxy-(1,3)dioxolane-4,5-dicarboyxlic acid diethyl ester; D004148:Dioxolanes; D004952:Esters; D009705:Nucleosides; D009841:Oligonucleotides; D009843:Oligoribonucleotides; D012313:RNA