Chemical Synthesis of Capped Oligoribonucleotides, m7G5′ pppAUG and m7G5′ pppAUGACC
- 1 March 1985
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 58 (3) , 850-860
- https://doi.org/10.1246/bcsj.58.850
Abstract
The fully-protected pAUG (15) and pAUGACC (21) were synthesized by the phosphotriester approach where the phenylthio group was employed as the internal and 5′-terminal phosphate-protecting groups. The partially unblocked oligomers (32) and (33), obtained by alkaline treatment of (15) and (21), were condensed with a capping reagent (1a) in the presence of imidazole by activation with silver nitrate to afford the capped trimer and hexamer protected with the acid-labile protecting groups, i.e., 4,4,′4″-trimethoxytrityl (TMTr), 4-monomethoxytrityl (MMTr), tetrahydropyran-2-yl (THP), and methoxymethylene (mM) groups. The protected capped oligomers were unblocked by a dilute HCl solution to afford m7G5′ pppAUG and m7G5′ pppAUGACC, which were purified by HPLC and characterized by enzyme assays.Keywords
This publication has 11 references indexed in Scilit:
- An effective method for the synthesis of the cap structure of eukaryotic messenger ribonucleic acidsTetrahedron Letters, 1984
- Synthesis of a dodecaribonucleotide, GUAUCAAUAAUG, by use of "fully" protected ribonucleotide building blocksJournal of the American Chemical Society, 1984
- Chemical synthesis of the 5′-terminal part bearing cap structure of messenger RNA of cytoplasmic polyhedrosis virus (CPV): m7G5′ pppAmpG and m7G5pppAmpGpUNucleic Acids Research, 1984
- Synthesis of oligoribonucleotides by use of S,S-diphenyl n-monomethoxytrityl ribonucleoside 3'-phosphorodithioatesTetrahedron, 1984
- Intramolecular stacking association and conformation properties of a ‘cap’ structure, m7G5;pppUm, and the related model compoundsNucleic Acids Research, 1983
- Studies on Chemical Synthesis of mRNAs. I. Synthesis and Properties of N2-Tritylguanosine Derivatives and Application to Synthesis of pGpUpUBulletin of the Chemical Society of Japan, 1982
- Synthesis and Properties of S,S-Diaryl Thymidine PhosphorodithioatesBulletin of the Chemical Society of Japan, 1981
- Synthesis and properties of S,S-diaryl nucleoside phosphorodithioates in oligonucleotide synthesisThe Journal of Organic Chemistry, 1979
- Capping of eucaryotic mRNAsCell, 1976
- Conversion of Mono- and Oligodeoxyribonucleotides to 5'-Triphosphates1Journal of the American Chemical Society, 1965