Literature DB >> 10793695

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

E Ohtsuka, S Tanaka, M Ikehara.   

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.

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Year:  1974        PMID： 10793695      PMCID： PMC344356          DOI： 10.1093/nar/1.10.1351

Source DB:  PubMed          Journal:  Nucleic Acids Res        ISSN： 0305-1048            Impact factor:   16.971


  10 in total

1.  Photochemistry of uridylyl-(3'--5')-uridine.

Authors:  I H Brown; K B Freeman; H E Johns
Journal:  J Mol Biol       Date:  1966-02       Impact factor: 5.469

2.  Specific chemical synthesis of ribonucleoside O-benzyl ethers.

Authors:  L F Christensen; A D Broom
Journal:  J Org Chem       Date:  1972-11-03       Impact factor: 4.354

3.  On the benzylation of nucleosides. II. A novel synthesis of 2'-o-benzyluridine.

Authors:  K Kikugawa; F Sato; T Tsuruo; N Imura; T Ukita
Journal:  Chem Pharm Bull (Tokyo)       Date:  1968-06       Impact factor: 1.645

4.  Studies on transfer ribonucleic acids and related compounds. II. A method for synthesis of protected ribooligonucleotides using a ribonuclease.

Authors:  E Ohtsuka; M Ubasawa; M Ikehara
Journal:  J Am Chem Soc       Date:  1970-06-03       Impact factor: 15.419

5.  Oligoribonucleotide synthesis from nucleoside 2'-O-benzyl ethers.

Authors:  B E Griffin; C B Reese; G F Stephenson; D R Trentham
Journal:  Tetrahedron Lett       Date:  1966-09       Impact factor: 2.415

6.  Studies on transfer ribonucleic acids and related compounds. VI. Synthesis of yeast alanine transfer ribonucleic acid 3'-terminal nonanucleotides and 5'-terminal hexanucleotides.

Authors:  E Otsuka; M Ubasawa; S Morioka; M Ikehara
Journal:  J Am Chem Soc       Date:  1973-07-11       Impact factor: 15.419

7.  Studies on transfer ribonucleic acids and related compounds. I. Synthesis of ribooligonucleotides using aromatic phosphoramidates as a protecting group.

Authors:  E Ohtsuka; K Murao; M Ubasawa; M Ikehara
Journal:  J Am Chem Soc       Date:  1970-06-03       Impact factor: 15.419

8.  Oligosaccharide synthesis on a light-sensitive solid support. I. The polymer and synthesis of isomaltose (6-O-alpha-D-glucopyranosyl-D-glucose).

Authors:  U Zehavi; A Patchornik
Journal:  J Am Chem Soc       Date:  1973-08-22       Impact factor: 15.419

9.  Polynucleotides. 23. A synthesis of ribodinucleoside monophosphates using nucleoside 5'-phosphates.

Authors:  E Otsuka; S Nakamura; M Yoneda; M Ikehara
Journal:  Nucleic Acids Res       Date:  1974-02       Impact factor: 16.971

10.  Studies on transfer ribonucleic acids and related compounds. 8(1). Further studies on aromatic phosphoramidates as a protecting group for phosphomonoesters.

Authors:  E Otsuka; A Honda; H Shigyo; S Morioka; T Sugiyama
Journal:  Nucleic Acids Res       Date:  1974-02       Impact factor: 16.971
  10 in total
  7 in total

Review 1.  Recent developments in the chemical synthesis of polynucleotides.

Authors:  E Ohtsuka; M Ikehara; D Söll
Journal:  Nucleic Acids Res       Date:  1982-11-11       Impact factor: 16.971

2.  Polynucleotides. XLII1. Limited addition of 2'O-onitrobenzyl nucleotides to the 3'-end of ribooligonucleotide with polynucleotide phosphorylase.

Authors:  M Ikehara; S Tanaka; T Fukui; E Ohtsuka
Journal:  Nucleic Acids Res       Date:  1976-11       Impact factor: 16.971

3.  Synthesis and NMR study of ribo-oligonucleotides forming a hammerhead-type RNA enzyme system.

Authors:  O Odai; H Kodama; H Hiroaki; T Sakata; T Tanaka; S Uesugi
Journal:  Nucleic Acids Res       Date:  1990-10-25       Impact factor: 16.971

4.  Selective 2'-benzoylation at the cis 2',3'-diols of protected ribonucleosides. New solid phase synthesis of RNA and DNA-RNA mixtures.

Authors:  T Kempe; F Chow; W I Sundquist; T J Nardi; B Paulson; S M Peterson
Journal:  Nucleic Acids Res       Date:  1982-11-11       Impact factor: 16.971

5.  Studies on transfer ribonucleic acids and related compounds. XL. Synthesis of an eicosaribonucleotide corresponding to residues 35-54 of tRNAfMet from E. coli.

Authors:  E Ohtsuka; K Fujiyama; M Ikehara
Journal:  Nucleic Acids Res       Date:  1981-07-24       Impact factor: 16.971

6.  Synthesis and incorporation of the phosphoramidite derivative of 2'-O-photocaged 3'-s-thioguanosine into oligoribonucleotides: substrate for probing the mechanism of RNA catalysis.

Authors:  Nan-Sheng Li; Nicole Tuttle; Jonathan P Staley; Joseph A Piccirilli
Journal:  J Org Chem       Date:  2014-03-31       Impact factor: 4.354

7.  Synthesis of Cyclic Peptides in SPPS with Npb-OH Photolabile Protecting Group.

Authors:  Tingting Chen; Gang Wang; Lin Tang; Hongpeng Yang; Jing Xu; Xiaoxue Wen; Yunbo Sun; Shuchen Liu; Tao Peng; Shouguo Zhang; Lin Wang
Journal:  Molecules       Date:  2022-03-29       Impact factor: 4.411
  7 in total

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