Opposite base specificity in excision of pyrimidine ring-opened 1,N6-ethenoadenine by thymine glycol-DNA-glycosylases

DNA Repair (Amst). 2002 Mar 28;1(3):251-7. doi: 10.1016/s1568-7864(01)00016-7.

Abstract

A highly mutagenic DNA lesion, 1,N6-ethenoadenine ( epsilon A) is chemically unstable and either depurinates or converts to a pyrimidine ring-opened product upon water molecule addition to the C(2)z.sbnd;N(3) bond in epsilon dA (compound B). Compound B subsequently undergoes deformylation to yield compound C, which depurinates in the final step of the epsilon A rearrangement pathway. We have previously shown that epsilon A rearrangement products are not repaired by human N-methylpurine-DNA-glycosylase, which excises parental epsilon A. Compound B was shown to be eliminated from a B:T pair by Escherichia coli formamidopyrimidine-DNA-glycosylase (Fpg protein) and endonuclease III (Nth protein). Fpg protein excised B also from a B:C pair, and much less efficiently from B:A and B:G pairs [J. Biol. Chem. 276 (2001) 21821]. Here we show that efficiency of B excision by the Nth protein also depends on the opposite base in the pair. Most efficient repair is observed when this derivative is paired with dG (Km=18nM, kcat=12) and is less favourable when paired with dC (Km=40nM, kcat=13) and dT (Km=32nM, kcat=11). In physiological conditions, compound B is probably not excised by the Nth-glycosylase from a B:A pair, or from a single-stranded DNA, since kinetic constants in these conditions are an order or two orders of magnitude higher than when B is paired with T, C or G. A similar specificity for B excision was found for Saccharomyces cerevisiae Ntg2-glycosylase. Thus, when paired with A, an epsilon A derivative might be more persistent than when paired with other bases and give rise to AT-->TA transversions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / metabolism*
  • DNA Damage*
  • DNA Glycosylases
  • DNA Primers / chemistry
  • DNA Repair*
  • DNA, Bacterial / chemistry
  • DNA, Bacterial / genetics
  • DNA, Bacterial / metabolism
  • DNA-(Apurinic or Apyrimidinic Site) Lyase
  • Deoxyribonuclease (Pyrimidine Dimer)*
  • Endodeoxyribonucleases / metabolism
  • Escherichia coli / enzymology
  • Escherichia coli / genetics
  • Escherichia coli Proteins*
  • Kinetics
  • N-Glycosyl Hydrolases / metabolism*
  • Oligodeoxyribonucleotides / chemistry
  • Oligodeoxyribonucleotides / metabolism
  • Saccharomyces cerevisiae / enzymology
  • Saccharomyces cerevisiae / genetics
  • Saccharomyces cerevisiae Proteins*
  • Thymidine / chemistry
  • Thymidine / metabolism

Substances

  • DNA Primers
  • DNA, Bacterial
  • Escherichia coli Proteins
  • Oligodeoxyribonucleotides
  • Saccharomyces cerevisiae Proteins
  • 1,N(6)-ethenoadenosine
  • Endodeoxyribonucleases
  • Deoxyribonuclease (Pyrimidine Dimer)
  • NTH protein, E coli
  • DNA Glycosylases
  • N-Glycosyl Hydrolases
  • DNA-(Apurinic or Apyrimidinic Site) Lyase
  • NTG2 protein, S cerevisiae
  • Adenosine
  • Thymidine