Studies on transfer ribonucleic acids and related compounds. IX(1)Ribo-oligonucleotide synthesis using a photosensitive o-nitrobenzyl protection at the 2′-hydroxyl group
- 1 January 1974
- journal article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 1 (10), 1351-1358
- https://doi.org/10.1093/nar/1.10.1351
Abstract
O-Nitrobenzyl group was introduced to the 2'-hydroxyl function of uridine via 2',3'-O-(dibutylstannylene) uridine. The benzylated uridine was protected at the 5'-hydroxyl group with monomethoxytrityl chloride and condensed with 2',3'-O-dibenzoyluridine 5'-phosphate or N,N',2',3'-O-tetrabenzoyladenosine 5'-phosphate using dicyclohexylcarbodiimide (DCC). o-Nitrobenzyl ether linkage of the dinucleotides was removed by UV irradiation with wavelength longer than 320 nm. Deprotected UpU and UpA thus obtained were characterized by RNase A digestion.Keywords
This publication has 10 references indexed in Scilit:
- Studies on transfer ribonucleic acids and related compounds. VIII(1). Further studies on aromatic phosphoramidates as a protecting group for phosphomonoestersNucleic Acids Research, 1974
- Polynucleotides. XXIII(1). A synthesis of ribodinucleoside monophosphates using nucleoside 5′-phosphatesNucleic Acids Research, 1974
- Oligosaccharide synthesis on a light-sensitive solid support. I. Polymer and synthesis of isomaltose (6-O-.alpha.-D-glucopyranosyl-D-glucose)Journal of the American Chemical Society, 1973
- Transfer ribonucleic acids and related compounds. VI. Synthesis of yeast alanine transfer ribonucleic acid 3'-terminal nonanucleotides and 5'-terminal hexanucleotidesJournal of the American Chemical Society, 1973
- Specific chemical synthesis of ribonucleoside O-benzyl ethersThe Journal of Organic Chemistry, 1972
- Transfer ribonucleic acids and related compounds. II. A method for synthesis of protected ribooligonucleotides using a ribonucleaseJournal of the American Chemical Society, 1970
- Transfer ribonucleic acids and related compounds. I. Synthesis of ribooligonucleotides using aromatic phosphoramidates as a protecting groupJournal of the American Chemical Society, 1970
- On the Benzylation of Nucleosides. II. A Novel Synthesis of 2'-O-BenzyluridineCHEMICAL & PHARMACEUTICAL BULLETIN, 1968
- Oligoribonucleotide synthesis from nucleoside 2′-Tetrahedron Letters, 1966
- Photochemistry of uridylyl-(3′→5′)-UridineJournal of Molecular Biology, 1966