Synthesis and Characterization of a Set of Four Dodecadeoxyribonucleoside Undecaphosphates Containing O6-Methylguanine opposite Adenine, Cytosine, Guanine, and Thymine

Barbara L. Gaffney, Luis A. Marky, Roger Jones

Research output: Contribution to journalArticle

94 Citations (Scopus)

Abstract

A set of four self-complementary dodecanucleoside undecaphosphates, d[CGNGAATTC(O6Me)GCG],1 where N = A, C, G, or T, has been synthesized by a phosphoramidite procedure. A single large-scale preparation of the nonamer d[DMT-GpApApTpTpCp(O6Me)GpCpG] was divided into four portions for synthesis of the dodecamers. The synthesis, purification (high-performance liquid chromatography), and characterization of each of these molecules are described. Each sequence forms a stable duplex, with a Tm between 19 and 26 °C lower than the Tm of the ‘parent molecule d-(CGCGAATTCGCG). The lowest melting sequence is the N = T molecule; the overall order is N = C > A > G > T. Thus O6-methylation of guanine creates a region of localized instability in DNA regardless of the base opposite the lesion, This instability, which could disrupt some regulatory process or event, may be as significant as or more significant than is the mutation itself to the oncogenic process initiated by alkylating agents.

Original languageEnglish (US)
Pages (from-to)5686-5691
Number of pages6
JournalBiochemistry
Volume23
Issue number24
DOIs
StatePublished - Jan 1 1984

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Thymine
Alkylating Agents
Cytosine
Guanine
Adenine
Methylation
Freezing
High Pressure Liquid Chromatography
Mutation
Molecules
DNA
High performance liquid chromatography
Purification
Melting
O-(6)-methylguanine
phosphoramidite

All Science Journal Classification (ASJC) codes

  • Biochemistry

Cite this

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title = "Synthesis and Characterization of a Set of Four Dodecadeoxyribonucleoside Undecaphosphates Containing O6-Methylguanine opposite Adenine, Cytosine, Guanine, and Thymine",
abstract = "A set of four self-complementary dodecanucleoside undecaphosphates, d[CGNGAATTC(O6Me)GCG],1 where N = A, C, G, or T, has been synthesized by a phosphoramidite procedure. A single large-scale preparation of the nonamer d[DMT-GpApApTpTpCp(O6Me)GpCpG] was divided into four portions for synthesis of the dodecamers. The synthesis, purification (high-performance liquid chromatography), and characterization of each of these molecules are described. Each sequence forms a stable duplex, with a Tm between 19 and 26 °C lower than the Tm of the ‘parent molecule d-(CGCGAATTCGCG). The lowest melting sequence is the N = T molecule; the overall order is N = C > A > G > T. Thus O6-methylation of guanine creates a region of localized instability in DNA regardless of the base opposite the lesion, This instability, which could disrupt some regulatory process or event, may be as significant as or more significant than is the mutation itself to the oncogenic process initiated by alkylating agents.",
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Synthesis and Characterization of a Set of Four Dodecadeoxyribonucleoside Undecaphosphates Containing O6-Methylguanine opposite Adenine, Cytosine, Guanine, and Thymine. / Gaffney, Barbara L.; Marky, Luis A.; Jones, Roger.

In: Biochemistry, Vol. 23, No. 24, 01.01.1984, p. 5686-5691.

Research output: Contribution to journalArticle

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