Home LiteratureArticle Details

PMID: 6856460 Published · ppublish English Journal Article Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, P.H.S.

Specifically alkylated DNA fragments. Synthesis and physical characterization of d[CGC(O6Me)GCG] and d[CGT(O6Me)GCG].

Nucleic acids research ·Vol. 11 ·No. 10 ·1983-05-25 ·Pages 3393-403

Kuzmich S, Marky LA, Jones RA

Abstract

Two hexamer DNA fragments containing a carcinogenic modified base, O6-methyl guanine, have been synthesized by a solid-phase phosphotriester method, in which the unmodified guanine residues present were O6 protected with the 4-nitrophenylethyl group. These two alkylated oligonucleotides were found to have similar Tm's about 40 degrees lower than the unmodified parent compound, d(CG)3. Moreover, the presence of the (O6Me)G appears to inhibit the B leads to Z transition, as determined by CD spectroscopy.

MeSH Terms

Base Sequence Circular Dichroism DNA Guanine/analogs & derivatives Indicators and Reagents Methylation Nucleic Acid Conformation Oligodeoxyribonucleotides/chemical synthesis Oligonucleotides/chemical synthesis Structure-Activity Relationship Temperature

Chemicals

Indicators and Reagents Oligodeoxyribonucleotides Oligonucleotides Guanine DNA O-(6)-methylguanine

Authors & Affiliations

3 authors, click to expand affiliations / ORCID

Kuzmich S

Marky L A

Jones R A

References (14)

14 references, click to expand

Possible relevance of O-6 alkylation of deoxyguanosine to the mutagenicity and carcinogenicity of nitrosamines and nitrosamides.
Nature. 1969 Jul 12;223(5202):206-7 PMID: 5791738
Salt-induced co-operative conformational change of a synthetic DNA: equilibrium and kinetic studies with poly (dG-dC).
J Mol Biol. 1972 Jun 28;67(3):375-96 PMID: 5045303
The properties of O 6 -methylguanine in templates for RNA polymerase.
Biochim Biophys Acta. 1973 May 10;308(2):310-6 PMID: 4706005
Repair of O6-methylguanine in adapted Escherichia coli.
Proc Natl Acad Sci U S A. 1978 Dec;75(12):6017-20 PMID: 282622
Synthesis and properties of O6-methyldeoxyguanylic acid and its copolymers with deoxycytidylic acid.
Biochim Biophys Acta. 1978 Dec 21;521(2):770-8 PMID: 737185
Molecular structure of a left-handed double helical DNA fragment at atomic resolution.
Nature. 1979 Dec 13;282(5740):680-6 PMID: 514347
Chemical synthesis of tridecanucleoside dodecaphosphate sequence of SV40 DNA.
Nucleic Acids Res. 1980 May 10;8(9):2039-53 PMID: 6253954
The origin of human cancers.
Nature. 1981 Jan 29;289(5796):353-7 PMID: 6258076
Mismatch correction at O6-methylguanine residues in E. coli DNA.
Nature. 1982 Apr 29;296(5860):868-9 PMID: 7040986
Solid phase synthesis of polynucleotides. VI. Further studies on polystyrene copolymers for the solid support.
Nucleic Acids Res. 1982 Mar 11;10(5):1755-69 PMID: 7071021
The influence of the purine 2-amino group on DNA conformation and stability. Synthesis and conformational analysis of d[T(2-aminoA)]3.
Nucleic Acids Res. 1982 Jul 24;10(14):4351-61 PMID: 7122239
Mechanism of activation of a human oncogene.
Nature. 1982 Nov 11;300(5888):143-9 PMID: 6290897
A point mutation is responsible for the acquisition of transforming properties by the T24 human bladder carcinoma oncogene.
Nature. 1982 Nov 11;300(5888):149-52 PMID: 7133135
Synthesis and physical characterization of the self-complementary, alternating pyrimidine/purine hexanucleotide d[CGTACG].
Nucleic Acids Res. 1982 Oct 25;10(20):6265-71 PMID: 7177847

Article Info

Journal

Nucleic acids research

Abbr.

Nucleic Acids Res

ISSN

0305-1048

DOI

10.1093/nar/11.10.3393

Published

1983-05-25

Pages

3393-403

Language

English

Region

England

NLM ID

0411011

PMCID

PMC325971

Subset

Grants

NIGMS NIH HHS · GM 23509 · United States

External Links

PubMed source DOI: 10.1093/nar/11.10.3393 PMC Full Text View journal details

Analysis Services

Specifically alkylated DNA fragments. Synthesis and physical characterization of d[CGC(O6Me)GCG] and d[CGT(O6Me)GCG].

Contact

WeChat Official Account