Identification by UV resonance Raman spectroscopy of an imino tautomer of 5-hydroxy-2'-deoxycytidine, a powerful base analog transition mutagen with a much higher unfavored tautomer frequency than that of the natural residue 2'-deoxycytidine

W. Suen, T. G. Spiro, Lawrence Sowers, J. R. Fresco

Research output: Contribution to journalArticle

59 Citations (Scopus)

Abstract

UV resonance Raman spectroscopy was used to detect and estimate the frequency of the unfavored imino tautomer of the transition mutagen 5- hydroxy-2'-deoxycytidine (HO5dCyt) in its anionic form. In DNA, this 2'- deoxycytidine analog arises from the oxidation of 2'-deoxycytidine and induces C → T transitions with 102 greater frequency than such spontaneous transitions. An imino tautomer marker carbonyl band (≃ 1650 cm-1) is enhanced at ≃65°C against an otherwise stable spectrum of bands associated with the favored amino tautomer. This band is similarly present in the UV resonance Raman spectra of the imino cytidine analogs N3-methylcytidine at high pH and N4-methoxy-2'-deoxycytidine at pH 7 and displays features attributable to the imino form of C residues and their derivatives. The fact that the imino tautomer of HO5dCyt occurs at a frequency consistent with its high mutagenic enhancement lends strong support to the hypothesis that unfavored base tautomers play important roles in the mispair intermediates of replication leading to substitution mutations.

Original languageEnglish (US)
Pages (from-to)4500-4505
Number of pages6
JournalProceedings of the National Academy of Sciences of the United States of America
Volume96
Issue number8
DOIs
StatePublished - Apr 13 1999
Externally publishedYes

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Deoxycytidine
Raman Spectrum Analysis
Mutagens
Cytidine
Mutation
DNA
5-hydroxy-2'-deoxycytidine

ASJC Scopus subject areas

  • Genetics
  • General

Cite this

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title = "Identification by UV resonance Raman spectroscopy of an imino tautomer of 5-hydroxy-2'-deoxycytidine, a powerful base analog transition mutagen with a much higher unfavored tautomer frequency than that of the natural residue 2'-deoxycytidine",
abstract = "UV resonance Raman spectroscopy was used to detect and estimate the frequency of the unfavored imino tautomer of the transition mutagen 5- hydroxy-2'-deoxycytidine (HO5dCyt) in its anionic form. In DNA, this 2'- deoxycytidine analog arises from the oxidation of 2'-deoxycytidine and induces C → T transitions with 102 greater frequency than such spontaneous transitions. An imino tautomer marker carbonyl band (≃ 1650 cm-1) is enhanced at ≃65°C against an otherwise stable spectrum of bands associated with the favored amino tautomer. This band is similarly present in the UV resonance Raman spectra of the imino cytidine analogs N3-methylcytidine at high pH and N4-methoxy-2'-deoxycytidine at pH 7 and displays features attributable to the imino form of C residues and their derivatives. The fact that the imino tautomer of HO5dCyt occurs at a frequency consistent with its high mutagenic enhancement lends strong support to the hypothesis that unfavored base tautomers play important roles in the mispair intermediates of replication leading to substitution mutations.",
author = "W. Suen and Spiro, {T. G.} and Lawrence Sowers and Fresco, {J. R.}",
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T1 - Identification by UV resonance Raman spectroscopy of an imino tautomer of 5-hydroxy-2'-deoxycytidine, a powerful base analog transition mutagen with a much higher unfavored tautomer frequency than that of the natural residue 2'-deoxycytidine

AU - Suen, W.

AU - Spiro, T. G.

AU - Sowers, Lawrence

AU - Fresco, J. R.

PY - 1999/4/13

Y1 - 1999/4/13

N2 - UV resonance Raman spectroscopy was used to detect and estimate the frequency of the unfavored imino tautomer of the transition mutagen 5- hydroxy-2'-deoxycytidine (HO5dCyt) in its anionic form. In DNA, this 2'- deoxycytidine analog arises from the oxidation of 2'-deoxycytidine and induces C → T transitions with 102 greater frequency than such spontaneous transitions. An imino tautomer marker carbonyl band (≃ 1650 cm-1) is enhanced at ≃65°C against an otherwise stable spectrum of bands associated with the favored amino tautomer. This band is similarly present in the UV resonance Raman spectra of the imino cytidine analogs N3-methylcytidine at high pH and N4-methoxy-2'-deoxycytidine at pH 7 and displays features attributable to the imino form of C residues and their derivatives. The fact that the imino tautomer of HO5dCyt occurs at a frequency consistent with its high mutagenic enhancement lends strong support to the hypothesis that unfavored base tautomers play important roles in the mispair intermediates of replication leading to substitution mutations.

AB - UV resonance Raman spectroscopy was used to detect and estimate the frequency of the unfavored imino tautomer of the transition mutagen 5- hydroxy-2'-deoxycytidine (HO5dCyt) in its anionic form. In DNA, this 2'- deoxycytidine analog arises from the oxidation of 2'-deoxycytidine and induces C → T transitions with 102 greater frequency than such spontaneous transitions. An imino tautomer marker carbonyl band (≃ 1650 cm-1) is enhanced at ≃65°C against an otherwise stable spectrum of bands associated with the favored amino tautomer. This band is similarly present in the UV resonance Raman spectra of the imino cytidine analogs N3-methylcytidine at high pH and N4-methoxy-2'-deoxycytidine at pH 7 and displays features attributable to the imino form of C residues and their derivatives. The fact that the imino tautomer of HO5dCyt occurs at a frequency consistent with its high mutagenic enhancement lends strong support to the hypothesis that unfavored base tautomers play important roles in the mispair intermediates of replication leading to substitution mutations.

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