Introduction of cationic charge into DNA near the major groove edge of a guanine•cytosine base pair: Characterization of oligodeoxynucleotides substituted with 7-aminomethyl-7-deaza-2′-deoxyguanosine

Manjori Ganguly, Ruo Wen Wang, Luis A Marky, Barry Gold

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

(Figure Presented) The replacement of the 7-N atom on guanine (G) with a C-H to give 7-deazaguanine (c7G) alters the electronic properties of the heterocyclic base and eliminates a potential major groove cation binding site, which affects the organization of salts and water in the major groove. This has a destabilizing effect on DNA. We report herein the characterization of DNA oligomers containing 7-(aminomethyl)-7-deazaguanine (1) residues using a variety of spectroscopic and thermodynamic approaches. 1 is an intramolecular model for the major groove binding of cations and basic amino acid residues to G. In contrast to c7G, the tethering of a cation in the major groove using 1 affords DNA that is as, or more, stable than the corresponding unmodified DNA. The stabilization is associated with the folding enthalpy and hydration.

Original languageEnglish (US)
Pages (from-to)12068-12069
Number of pages2
JournalJournal of the American Chemical Society
Volume131
Issue number34
DOIs
StatePublished - Sep 2 2009

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Oligodeoxyribonucleotides
Base Pairing
DNA
Cations
Positive ions
Basic Amino Acids
Guanine
Binding sites
Thermodynamics
Oligomers
Electronic properties
Hydration
Amino acids
Enthalpy
Stabilization
Salts
Binding Sites
Atoms
7-aminomethyl-7-deaza-2'-deoxyguanosine
Water

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

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abstract = "(Figure Presented) The replacement of the 7-N atom on guanine (G) with a C-H to give 7-deazaguanine (c7G) alters the electronic properties of the heterocyclic base and eliminates a potential major groove cation binding site, which affects the organization of salts and water in the major groove. This has a destabilizing effect on DNA. We report herein the characterization of DNA oligomers containing 7-(aminomethyl)-7-deazaguanine (1) residues using a variety of spectroscopic and thermodynamic approaches. 1 is an intramolecular model for the major groove binding of cations and basic amino acid residues to G. In contrast to c7G, the tethering of a cation in the major groove using 1 affords DNA that is as, or more, stable than the corresponding unmodified DNA. The stabilization is associated with the folding enthalpy and hydration.",
author = "Manjori Ganguly and Wang, {Ruo Wen} and Marky, {Luis A} and Barry Gold",
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T1 - Introduction of cationic charge into DNA near the major groove edge of a guanine•cytosine base pair

T2 - Characterization of oligodeoxynucleotides substituted with 7-aminomethyl-7-deaza-2′-deoxyguanosine

AU - Ganguly, Manjori

AU - Wang, Ruo Wen

AU - Marky, Luis A

AU - Gold, Barry

PY - 2009/9/2

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N2 - (Figure Presented) The replacement of the 7-N atom on guanine (G) with a C-H to give 7-deazaguanine (c7G) alters the electronic properties of the heterocyclic base and eliminates a potential major groove cation binding site, which affects the organization of salts and water in the major groove. This has a destabilizing effect on DNA. We report herein the characterization of DNA oligomers containing 7-(aminomethyl)-7-deazaguanine (1) residues using a variety of spectroscopic and thermodynamic approaches. 1 is an intramolecular model for the major groove binding of cations and basic amino acid residues to G. In contrast to c7G, the tethering of a cation in the major groove using 1 affords DNA that is as, or more, stable than the corresponding unmodified DNA. The stabilization is associated with the folding enthalpy and hydration.

AB - (Figure Presented) The replacement of the 7-N atom on guanine (G) with a C-H to give 7-deazaguanine (c7G) alters the electronic properties of the heterocyclic base and eliminates a potential major groove cation binding site, which affects the organization of salts and water in the major groove. This has a destabilizing effect on DNA. We report herein the characterization of DNA oligomers containing 7-(aminomethyl)-7-deazaguanine (1) residues using a variety of spectroscopic and thermodynamic approaches. 1 is an intramolecular model for the major groove binding of cations and basic amino acid residues to G. In contrast to c7G, the tethering of a cation in the major groove using 1 affords DNA that is as, or more, stable than the corresponding unmodified DNA. The stabilization is associated with the folding enthalpy and hydration.

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