Modification of Adenine and Cytosine Derivatives with Bromoacetaldehyde

Kikuko Kayasuga-Mikado, Teruko Hashimoto, Tomoe Negishi, Kazuo Negishi, Hikoya Hayatsu

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

Bromoacetaldehyde reacted with adenosine 5′-phosphate and cytidine more rapidly than chloroacetaldehyde to give 1,N6-ethenoadenosine 5′-phosphate and 3,N4-ethenocytidine, respectively. The pH-dependence of the rates of these reactions was similar to that of the chloroacetaldehyde modifications reported in the literature; i.e. the reactions proceed smoothly in the pH range of 5 to 7. When applied to polynucleotides, bromoacetaldehyde reacted with adenine and cytosine residues located in single-stranded regions but not with those in double-stranded regions. Guanosine 5′-phosphate reacted with bromoacetaldehyde at pH 7 but only very slowly at pH 5. Bromoacetaldehyde may be useful as a more reactive subtitute for chloroacetaldehyde. Bromoacetaldehyde showed little mutagenic activity when assayed on Salmonella typhymurium TA 100.

Original languageEnglish
Pages (from-to)932-938
Number of pages7
JournalChemical and Pharmaceutical Bulletin
Volume28
Issue number3
DOIs
Publication statusPublished - Jan 1 1980

Keywords

  • 1,N-ethenoadenosine 5′-phosphate
  • 3,N-ethenocytidine
  • 3,N-ethenocytosine
  • adenosine 5′-phosphate
  • bromoacetaldehyde
  • chemical modification
  • cytidine
  • guanosine 5′-phosphate
  • mutagenicity
  • polynucleotides

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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  • Cite this

    Kayasuga-Mikado, K., Hashimoto, T., Negishi, T., Negishi, K., & Hayatsu, H. (1980). Modification of Adenine and Cytosine Derivatives with Bromoacetaldehyde. Chemical and Pharmaceutical Bulletin, 28(3), 932-938. https://doi.org/10.1248/cpb.28.932