Base-pair induced shifts in the tautomeric equilibrium of a modified DNA base

G. Victor Fazakerley, Zofia Gdaniec, Lawrence Sowers

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

We have examined the base-pairing properties of N4-methoxycytosine (mo4C), a mutagenic base analog, in DNA by nuclear magnetic resonance spectroscopy. Unlike standard bases, the tautomeric equilibrium of mo4C could be strongly influenced by base-pair formation. Paired with A, mo4C is found predominantly in the imino configuration in Watson-Crick geometry. However, when paired with G, two structurally distinct configurations are observed in equilibrium with one another. In one configuration, mo4C is in the amino form paired with G in Watson-Crick geometry. In the second species, mo4C is in the imino configuration paired with G in a wobble geometry. This is the first demonstration of base-pair induced tautomeric shifts in DNA and supports the hypothesis that rare tautomeric forms may be involved in mutagenesis.

Original languageEnglish (US)
Pages (from-to)6-10
Number of pages5
JournalJournal of Molecular Biology
Volume230
Issue number1
StatePublished - 1993
Externally publishedYes

Fingerprint

Base Pairing
DNA
Mutagenesis
Magnetic Resonance Spectroscopy

Keywords

  • DNA
  • Mutagenesis
  • n.m.r
  • Oligonucleotide
  • Tautomerism

ASJC Scopus subject areas

  • Virology

Cite this

Base-pair induced shifts in the tautomeric equilibrium of a modified DNA base. / Fazakerley, G. Victor; Gdaniec, Zofia; Sowers, Lawrence.

In: Journal of Molecular Biology, Vol. 230, No. 1, 1993, p. 6-10.

Research output: Contribution to journalArticle

Fazakerley, G. Victor ; Gdaniec, Zofia ; Sowers, Lawrence. / Base-pair induced shifts in the tautomeric equilibrium of a modified DNA base. In: Journal of Molecular Biology. 1993 ; Vol. 230, No. 1. pp. 6-10.
@article{3816152bb6704090a72830c158af8855,
title = "Base-pair induced shifts in the tautomeric equilibrium of a modified DNA base",
abstract = "We have examined the base-pairing properties of N4-methoxycytosine (mo4C), a mutagenic base analog, in DNA by nuclear magnetic resonance spectroscopy. Unlike standard bases, the tautomeric equilibrium of mo4C could be strongly influenced by base-pair formation. Paired with A, mo4C is found predominantly in the imino configuration in Watson-Crick geometry. However, when paired with G, two structurally distinct configurations are observed in equilibrium with one another. In one configuration, mo4C is in the amino form paired with G in Watson-Crick geometry. In the second species, mo4C is in the imino configuration paired with G in a wobble geometry. This is the first demonstration of base-pair induced tautomeric shifts in DNA and supports the hypothesis that rare tautomeric forms may be involved in mutagenesis.",
keywords = "DNA, Mutagenesis, n.m.r, Oligonucleotide, Tautomerism",
author = "Fazakerley, {G. Victor} and Zofia Gdaniec and Lawrence Sowers",
year = "1993",
language = "English (US)",
volume = "230",
pages = "6--10",
journal = "Journal of Molecular Biology",
issn = "0022-2836",
publisher = "Academic Press Inc.",
number = "1",

}

TY - JOUR

T1 - Base-pair induced shifts in the tautomeric equilibrium of a modified DNA base

AU - Fazakerley, G. Victor

AU - Gdaniec, Zofia

AU - Sowers, Lawrence

PY - 1993

Y1 - 1993

N2 - We have examined the base-pairing properties of N4-methoxycytosine (mo4C), a mutagenic base analog, in DNA by nuclear magnetic resonance spectroscopy. Unlike standard bases, the tautomeric equilibrium of mo4C could be strongly influenced by base-pair formation. Paired with A, mo4C is found predominantly in the imino configuration in Watson-Crick geometry. However, when paired with G, two structurally distinct configurations are observed in equilibrium with one another. In one configuration, mo4C is in the amino form paired with G in Watson-Crick geometry. In the second species, mo4C is in the imino configuration paired with G in a wobble geometry. This is the first demonstration of base-pair induced tautomeric shifts in DNA and supports the hypothesis that rare tautomeric forms may be involved in mutagenesis.

AB - We have examined the base-pairing properties of N4-methoxycytosine (mo4C), a mutagenic base analog, in DNA by nuclear magnetic resonance spectroscopy. Unlike standard bases, the tautomeric equilibrium of mo4C could be strongly influenced by base-pair formation. Paired with A, mo4C is found predominantly in the imino configuration in Watson-Crick geometry. However, when paired with G, two structurally distinct configurations are observed in equilibrium with one another. In one configuration, mo4C is in the amino form paired with G in Watson-Crick geometry. In the second species, mo4C is in the imino configuration paired with G in a wobble geometry. This is the first demonstration of base-pair induced tautomeric shifts in DNA and supports the hypothesis that rare tautomeric forms may be involved in mutagenesis.

KW - DNA

KW - Mutagenesis

KW - n.m.r

KW - Oligonucleotide

KW - Tautomerism

UR - http://www.scopus.com/inward/record.url?scp=0027510365&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0027510365&partnerID=8YFLogxK

M3 - Article

C2 - 8450552

AN - SCOPUS:0027510365

VL - 230

SP - 6

EP - 10

JO - Journal of Molecular Biology

JF - Journal of Molecular Biology

SN - 0022-2836

IS - 1

ER -