Skip to main content
PMC home page
Nucleic Acids Research logoLink to Nucleic Acids Research
. 1974 Oct;1(10):1351–1357. doi: 10.1093/nar/1.10.1351

Studies on transfer ribonucleic acids and related compounds. IX(1) Ribooligonucleotide synthesis using a photosensitive o-nitrobenzyl protection at the 2′-hydroxyl group

E Ohtsuka 1, S Tanaka 1, M Ikehara 1
PMCID: PMC344356  PMID: 10793695

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.

Full text

PDF
1353

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Brown I. H., Freeman K. B., Johns H. E. Photochemistry of uridylyl-(3'--5')-uridine. J Mol Biol. 1966 Feb;15(2):640–662. doi: 10.1016/s0022-2836(66)80133-x. [DOI] [PubMed] [Google Scholar]
  2. Christensen L. F., Broom A. D. Specific chemical synthesis of ribonucleoside O-benzyl ethers. J Org Chem. 1972 Nov 3;37(22):3398–3401. doi: 10.1021/jo00795a003. [DOI] [PubMed] [Google Scholar]
  3. Griffin B. E., Reese C. B., Stephenson G. F., Trentham D. R. Oligoribonucleotide synthesis from nucleoside 2'-O-benzyl ethers. Tetrahedron Lett. 1966 Sep;36:4349–4354. doi: 10.1016/s0040-4039(00)76063-1. [DOI] [PubMed] [Google Scholar]
  4. Kikugawa K., Sato F., Tsuruo T., Imura N., Ukita T. On the benzylation of nucleosides. II. A novel synthesis of 2'-o-benzyluridine. Chem Pharm Bull (Tokyo) 1968 Jun;16(6):1110–1115. doi: 10.1248/cpb.16.1110. [DOI] [PubMed] [Google Scholar]
  5. Ohtsuka E., Murao K., Ubasawa M., Ikehara M. Studies on transfer ribonucleic acids and related compounds. I. Synthesis of ribooligonucleotides using aromatic phosphoramidates as a protecting group. J Am Chem Soc. 1970 Jun 3;92(11):3441–3445. doi: 10.1021/ja00714a036. [DOI] [PubMed] [Google Scholar]
  6. Ohtsuka E., Ubasawa M., Ikehara M. Studies on transfer ribonucleic acids and related compounds. II. A method for synthesis of protected ribooligonucleotides using a ribonuclease. J Am Chem Soc. 1970 Jun 3;92(11):3445–3451. doi: 10.1021/ja00714a037. [DOI] [PubMed] [Google Scholar]
  7. Otsuka E., Honda A., Shigyo H., Morioka S., Sugiyama T. Studies on transfer ribonucleic acids and related compounds. 8(1). Further studies on aromatic phosphoramidates as a protecting group for phosphomonoesters. Nucleic Acids Res. 1974 Feb;1(2):223–234. doi: 10.1093/nar/1.2.223. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Otsuka E., Nakamura S., Yoneda M., Ikehara M. Polynucleotides. 23. A synthesis of ribodinucleoside monophosphates using nucleoside 5'-phosphates. Nucleic Acids Res. 1974 Feb;1(2):323–329. doi: 10.1093/nar/1.2.323. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Otsuka E., Ubasawa M., Morioka S., Ikehara M. Studies on transfer ribonucleic acids and related compounds. VI. Synthesis of yeast alanine transfer ribonucleic acid 3'-terminal nonanucleotides and 5'-terminal hexanucleotides. J Am Chem Soc. 1973 Jul 11;95(14):4725–4733. doi: 10.1021/ja00795a042. [DOI] [PubMed] [Google Scholar]
  10. Zehavi U., Patchornik A. Oligosaccharide synthesis on a light-sensitive solid support. I. The polymer and synthesis of isomaltose (6-O-alpha-D-glucopyranosyl-D-glucose). J Am Chem Soc. 1973 Aug 22;95(17):5673–5677. doi: 10.1021/ja00798a036. [DOI] [PubMed] [Google Scholar]

Articles from Nucleic Acids Research are provided here courtesy of Oxford University Press

RESOURCES