Literature DB >> 2395642

Chemical synthesis and spontaneous glycosidic hydrolysis of 3-methyl-2'-deoxyguanosine and 2'-deoxywyosine [1].

B Golankiewicz1, T Ostrowski, W Folkman.   

Abstract

3-methyl-2'-deoxyguanosine (1a) is obtained from 2'-deoxyguanosine by a reaction sequence involving conversion into tricyclic 1,N-2-isopropeno derivative (4-desmethyl-2'-deoxywyosine, 3a) followed by methylation which results in 2'-deoxywyosine (2a) and final removal of the 1,N-2 blocking system. Compounds 1a and 2a undergo spontaneous hydrolytic cleavage of their glycosidic bonds at pH 7, 37 degrees C, which makes them the most labile of all known nucleosides composed of structural units occurring in nature.

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Year:  1990        PMID： 2395642      PMCID： PMC331943          DOI： 10.1093/nar/18.16.4779

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


  11 in total

1.  Studies on polynucleotides, lxviii the primary structure of yeast phenylalanine transfer RNA.

Authors:  U L Rajbhandary; S H Chang; A Stuart; R D Faulkner; R M Hoskinson; H G Khorana
Journal:  Proc Natl Acad Sci U S A       Date:  1967-03       Impact factor: 11.205

2.  15N NMR spectra of wyosine and related ribonucleosides.

Authors:  B Golankiewicz; W Folkman; H Rosemeyer; F Seela
Journal:  Nucleic Acids Res       Date:  1987-11-11       Impact factor: 16.971

3.  A specific modification next to the anticodon of phenylalanine transfer ribonucleic acid.

Authors:  R Thiebe; H G Zachau
Journal:  Eur J Biochem       Date:  1968-09-24

4.  Preparative enzymic synthesis of nucleoside-5'-phosphates.

Authors:  J Giziewicz; D Shugar
Journal:  Acta Biochim Pol       Date:  1975       Impact factor: 2.149

5.  Kinetics and mechanism of the acid-catalyzed hydrolysis of a hypermodified nucleoside wyosine and its 5'-monophosphate.

Authors:  B Golankiewicz; E Zielonacka-Lis; W Folkman
Journal:  Nucleic Acids Res       Date:  1985-04-11       Impact factor: 16.971

6.  Synthesis of modified nucleoside 3',5'-bisphosphates and their incorporation into oligoribonucleotides with T4 RNA ligase.

Authors:  J R Barrio; M C Barrio; N J Leonard; T E England; O C Uhlenbeck
Journal:  Biochemistry       Date:  1978-05-30       Impact factor: 3.162

7.  Synthesis of N2,3-ethenodeoxyguanosine, N2,3-ethenodeoxyguanosine 5'-phosphate, and N2,3-ethenodeoxyguanosine 5'-triphosphate. Stability of the glycosyl bond in the monomer and in poly(dG,epsilon dG-dC).

Authors:  J T Kuśmierek; W Folkman; B Singer
Journal:  Chem Res Toxicol       Date:  1989 Jul-Aug       Impact factor: 3.739

8.  Removal of minor methylation products 7-methyladenine and 3-methylguanine from DNA of Escherichia coli treated with dimethyl sulphate.

Authors:  P D Lawley; W Warren
Journal:  Chem Biol Interact       Date:  1976-02       Impact factor: 5.192

9.  Methylation of desmethyl analogue of Y nucleosides. Wyosine from guanosine.

Authors:  B Golankiewicz; W Folkman
Journal:  Nucleic Acids Res       Date:  1983-08-11       Impact factor: 16.971

10.  Mutagenicity of carcinogenic methylating agents is associated with a specific DNA modification.

Authors:  R F Newbold; W Warren; A S Medcalf; J Amos
Journal:  Nature       Date:  1980-02-07       Impact factor: 49.962
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  1 in total

1.  Biosynthesis of wyosine derivatives in tRNA: an ancient and highly diverse pathway in Archaea.

Authors:  Valérie de Crécy-Lagard; Céline Brochier-Armanet; Jaunius Urbonavicius; Bernard Fernandez; Gabriela Phillips; Benjamin Lyons; Akiko Noma; Sophie Alvarez; Louis Droogmans; Jean Armengaud; Henri Grosjean
Journal:  Mol Biol Evol       Date:  2010-04-09       Impact factor: 16.240
  1 in total

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