Literature DB >> 1886763

Solid-phase synthesis of DNA fragments containing the modified base 7-hydro-8-oxo-2'-deoxyguanosine.

H C Roelen1, C P Saris, H F Brugghe, H van den Elst, J G Westra, G A van der Marel, J H van Boom.   

Abstract

The 5'-(4,4'-dimethoxytrityl) protected 3'-(2-cyanoethoxy)-N,N-diisopropylphosphoramidite of 7-hydro-8-oxo-2'-deoxy-guanosine, the exocyclic amino and lactam functions of which are protected with acetyl and diphenylcarbamoyl groups, respectively, has been prepared from the 8-bromo derivatives of deoxy- and riboguanosine. This synthon, in combination with standard d-nucleoside 3'-(2-cyanoethoxy)-N,N-diisopropylphosphoramidites, was applied successfully to a solid-phase synthesis. Well-defined oligodeoxyribonucleotides containing a 7-hydro-8-oxo-2'-deoxyguanosine residue at predetermined positions were obtained after deprotection with methanolic ammonia and purification by gel filtration.

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Year:  1991        PMID： 1886763      PMCID： PMC328621          DOI： 10.1093/nar/19.16.4361

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


  23 in total

1.  DNA damage by 8-methoxypsoralen plus near ultraviolet light (PUVA) and its repair in Escherichia coli: genetic analysis.

Authors:  J Holland; I B Holland; S I Ahmad
Journal:  Mutat Res       Date:  1991-05       Impact factor: 2.433

2.  An ab initio molecular orbital study on the characteristics of 8-hydroxyguanine.

Authors:  M Aida; S Nishimura
Journal:  Mutat Res       Date:  1987-10       Impact factor: 2.433

3.  Mechanistic studies of ionizing radiation and oxidative mutagenesis: genetic effects of a single 8-hydroxyguanine (7-hydro-8-oxoguanine) residue inserted at a unique site in a viral genome.

Authors:  M L Wood; M Dizdaroglu; E Gajewski; J M Essigmann
Journal:  Biochemistry       Date:  1990-07-31       Impact factor: 3.162

4.  Modification of guanine bases by nucleoside phosphoramidite reagents during the solid phase synthesis of oligonucleotides.

Authors:  R T Pon; M J Damha; K K Ogilvie
Journal:  Nucleic Acids Res       Date:  1985-09-25       Impact factor: 16.971

5.  Application of 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite for in situ preparation of deoxyribonucleoside phosphoramidites and their use in polymer-supported synthesis of oligodeoxyribonucleotides.

Authors:  J Nielsen; M Taagaard; J E Marugg; J H van Boom; O Dahl
Journal:  Nucleic Acids Res       Date:  1986-09-25       Impact factor: 16.971

6.  Structural and conformational analyses of 8-hydroxy-2'-deoxyguanosine.

Authors:  S J Culp; B P Cho; F F Kadlubar; F E Evans
Journal:  Chem Res Toxicol       Date:  1989 Nov-Dec       Impact factor: 3.739

7.  2',3'-carbonates of 8-hydroxypurine nucleosides.

Authors:  K K Ogilvie; L Slotin
Journal:  J Org Chem       Date:  1971-08-27       Impact factor: 4.354

8.  Prevention of guanine modification and chain cleavage during the solid phase synthesis of oligonucleotides using phosphoramidite derivatives.

Authors:  R T Pon; N Usman; M J Damha; K K Ogilvie
Journal:  Nucleic Acids Res       Date:  1986-08-26       Impact factor: 16.971

9.  Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG.

Authors:  S Shibutani; M Takeshita; A P Grollman
Journal:  Nature       Date:  1991-01-31       Impact factor: 49.962

10.  NMR structural studies of the ionizing radiation adduct 7-hydro-8-oxodeoxyguanosine (8-oxo-7H-dG) opposite deoxyadenosine in a DNA duplex. 8-Oxo-7H-dG(syn).dA(anti) alignment at lesion site.

Authors:  M Kouchakdjian; V Bodepudi; S Shibutani; M Eisenberg; F Johnson; A P Grollman; D J Patel
Journal:  Biochemistry       Date:  1991-02-05       Impact factor: 3.162
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  3 in total

1.  Repair and replication of plasmids with site-specific 8-oxodG and 8-AAFdG residues in normal and repair-deficient human cells.

Authors:  J C Klein; M J Bleeker; C P Saris; H C Roelen; H F Brugghe; H van den Elst; G A van der Marel; J H van Boom; J G Westra; E Kriek
Journal:  Nucleic Acids Res       Date:  1992-09-11       Impact factor: 16.971

2.  Characterization of a mammalian homolog of the Escherichia coli MutY mismatch repair protein.

Authors:  J P McGoldrick; Y C Yeh; M Solomon; J M Essigmann; A L Lu
Journal:  Mol Cell Biol       Date:  1995-02       Impact factor: 4.272

3.  Synthesis and hydrolysis of oligodeoxyribonucleotides containing 2-aminopurine.

Authors:  J Fujimoto; Z Nuesca; M Mazurek; L C Sowers
Journal:  Nucleic Acids Res       Date:  1996-02-15       Impact factor: 16.971
  3 in total

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