Selective 2′-benzoylation at the 2′, 3′-diols of protected ribonucleosides. New solid phase synthesis of RNA and DNA-RNA mixtures
Open Access
- 1 January 1982
- journal article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 10 (21) , 6695-6714
- https://doi.org/10.1093/nar/10.21.6695
Abstract
5′–0–(Dimethoxytrityl)–2′–0–(benzoyl or 3, 4, 5–trimethoxybenzoyl)–base protected ribonucleosides have been prepared by selective benzoylation of the 2′–hydroxyl group. The isomerization of the 2′–benzoates to the 3'–benzoates was studied. The protected ribonucleosides have been converted to either methylphosphochloridites or methylphosphoamidites and used to synthesize oligoribonucleotides on silica gel solid support. The synthetic RNA were deprotected and isolated using conditions that minimize inter-nucleotide cleavage. The use of 2′–benzoates as protecting groups for ribonucleosides has made it possible to easily prepare and isolate mixtures of DNA and RNA.Keywords
This publication has 18 references indexed in Scilit:
- The Use of Primed Synthesis by DNA Polymerase I to Study an Intercistronic Sequence of ΦX‐174 DNAEuropean Journal of Biochemistry, 1975
- Studies on transfer ribonucleic acids and related compounds. IX(1)Ribo-oligonucleotide synthesis using a photosensitive o-nitrobenzyl protection at the 2′-hydroxyl groupNucleic Acids Research, 1974
- Use of DNA Polymerase I Primed by a Synthetic Oligonucleotide to Determine a Nucleotide Sequence in Phage f1 DNAProceedings of the National Academy of Sciences, 1973
- Specific chemical synthesis of ribonucleoside O-benzyl ethersThe Journal of Organic Chemistry, 1972
- On the Benzylation of Nucleosides. II. A Novel Synthesis of 2'-O-BenzyluridineCHEMICAL & PHARMACEUTICAL BULLETIN, 1968
- The synthesis of oligoribonucleotides—IIITetrahedron, 1967
- The synthesis of oligoribonucleotides—IITetrahedron, 1967
- Oligoribonucleotide synthesis from nucleoside 2′-Tetrahedron Letters, 1966
- Orientation of ribonucleoside derivatives by proton magentic resonance spectroscopyTetrahedron, 1966
- Acyl migration in ribonucleoside derivativesTetrahedron Letters, 1965