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PMID: 3737416 Published · ppublish English Journal Article Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, P.H.S.

Synthesis and properties of defined DNA oligomers containing base mispairs involving 2-aminopurine.

Nucleic acids research ·Vol. 14 ·No. 14 ·1986-07-25 ·Pages 5869-84

Eritja R, Kaplan BE, Mhaskar D, Sowers LC, Petruska J, Goodman MF

Abstract

DNA heptamers containing the mutagenic base analogue 2-aminopurine (AP) have been chemically synthesized and physically characterized. We report on the relative stabilities of base pairs between AP and each of the common DNA bases, as determined from heptamer duplex melts at 275 and 330 nm. Base pairs are ranked in order of decreasing stability: AP.T greater than AP.A greater than AP.C greater than AP.G. It is of interest that AP.A is more stable than AP.C even though DNA polymerase strongly favors the formation of AP.C over AP.A base pairs. Comparisons of melting profiles at 330 nm and 275 nm indicate that AP.T, AP.A, and AP.C base pairs are annealed in heptamer duplexes and melt 2-3 degrees prior to surrounding base pairs, whereas AP.G appears not to be annealed.

MeSH Terms
2-Aminopurine Adenine/analogs & derivatives Base Composition Base Sequence DNA/chemical synthesis Hydrogen Bonding Indicators and Reagents Magnetic Resonance Spectroscopy Oligodeoxyribonucleotides/chemical synthesis Spectrophotometry, Ultraviolet
Chemicals
Indicators and Reagents Oligodeoxyribonucleotides 2-Aminopurine DNA Adenine
Authors & Affiliations
6 authors, click to expand affiliations / ORCID
Eritja R
Kaplan B E
Mhaskar D
Sowers L C
Petruska J
Goodman M F
References (20)
20 references, click to expand
  1. Preparation and properties of poly 2-aminopurine ribotidylic acid.
    Acta Biochim Pol. 1973;20(3):271-84 PMID: 4584213
  2. THE DIFFERENCE BETWEEN SPONTANEOUS AND BASE-ANALOGUE INDUCED MUTATIONS OF PHAGE T4.
    Proc Natl Acad Sci U S A. 1959 Apr;45(4):622-33 PMID: 16590424
  3. Complementary base pairing and the origin of substitution mutations.
    Nature. 1976 Sep 23;263(5575):285-9 PMID: 958482
  4. On the molecular basis of transition mutations: frequencies of forming 2-aminopurine.cytosine and adenine.cytosine base mispairs in vitro.
    Proc Natl Acad Sci U S A. 1981 May;78(5):2864-8 PMID: 6942407
  5. Reversal of mutant phenotypes by 5-fluorouracil: an approach to nucleotide sequences in messenger-RNA.
    Proc Natl Acad Sci U S A. 1962 Apr 15;48:532-46 PMID: 13877975
  6. Asymmetry in forming 2-aminopurine . hydroxymethylcytosine heteroduplexes; A model giving misincorporation frequencies and rounds of DNA replication from base-pair populations in vivo.
    J Mol Biol. 1979 Nov 25;135(1):1-22 PMID: 529285
  7. Dialkylformamidines: depurination resistant N6-protecting group for deoxyadenosine.
    Nucleic Acids Res. 1983 Nov 25;11(22):8031-6 PMID: 6606157
  8. Detection of a guanine X adenine base pair in a decadeoxyribonucleotide by proton magnetic resonance spectroscopy.
    Proc Natl Acad Sci U S A. 1983 Jul;80(14):4263-5 PMID: 6576336
  9. Influence of neighboring bases on DNA polymerase insertion and proofreading fidelity.
    J Biol Chem. 1985 Jun 25;260(12):7533-9 PMID: 3158658
  10. Influence of local nucleotide sequence on substitution of 2-aminopurine for adenine during deoxyribonucleic acid synthesis in vitro.
    Biochemistry. 1983 Oct 11;22(21):4905-15 PMID: 6357277
  11. Evidence of 2-aminopurine-cytosine base mispairs involving two hydrogen bonds.
    J Biol Chem. 1983 Nov 10;258(21):12842-6 PMID: 6630209
  12. 2-Aminopurine.
    Mutat Res. 1980 Jan;75(1):1-47 PMID: 6987505
  13. Specific amino acid substitutions in bacterioopsin: Replacement of a restriction fragment in the structural gene by synthetic DNA fragments containing altered codons.
    Proc Natl Acad Sci U S A. 1984 Apr;81(8):2285-9 PMID: 16593452
  14. Solid phase synthesis of polynucleotides. VI. Further studies on polystyrene copolymers for the solid support.
    Nucleic Acids Res. 1982 Mar 11;10(5):1755-69 PMID: 7071021
  15. Mutation as an error in base pairing.
    Biochem Biophys Res Commun. 1960 Sep;3:275-80 PMID: 13744470
  16. On the molecular basis of transition mutations. Frequency of forming 2-aminopurine-cytosine base mispairs in the G X C----A X T mutational pathway by T4 DNA polymerase in vitro.
    J Biol Chem. 1984 Oct 10;259(19):11713-7 PMID: 6480580
  17. Solid-phase synthesis of polynucleotides. VIII: A simplified synthesis of oligodeoxyribonucleotides.
    Cold Spring Harb Symp Quant Biol. 1983;47 Pt 1:383-91 PMID: 6574851
  18. DNA sequence analysis: a general, simple and rapid method for sequencing large oligodeoxyribonucleotide fragments by mapping.
    Nucleic Acids Res. 1974 Mar;1(3):331-53 PMID: 10793670
  19. Comparison of nucleotide interactions in water, proteins, and vacuum: model for DNA polymerase fidelity.
    Proc Natl Acad Sci U S A. 1986 Mar;83(6):1559-62 PMID: 3456600
  20. Studies on the biochemical basis of spontaneous mutation. II. The incorporation of a base and its analogue into DNA by wild-type, mutator and antimutator DNA polymerases.
    J Mol Biol. 1974 Sep 15;88(2):409-21 PMID: 4616089
Article Info
Journal
Nucleic acids research
Abbr.
Nucleic Acids Res
ISSN
0305-1048
Published
1986-07-25
Pages
5869-84
Language
English
Region
England
NLM ID
0411011
PMCID
PMC311597
Subset
IM
Grants
NIGMS NIH HHS · GM21422 · United States
NIGMS NIH HHS · GM33863 · United States
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