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Base-boronated dinucleotides: synthesis and effect of N7-cyanoborane substitution on the base protons.

Publication ,  Journal Article
Hasan, A; Li, H; Tomasz, J; Shaw, BR
Published in: Nucleic acids research
June 1996

Boron-modified nucleic acids comprise a new set of DNA mimics that have potential biological and therapeutic applications. A series of nine dinucleotides containing N7-cyanoborane-2'-deoxyguanosine ((7b)dG) at the 3', 5' or both positions of the phosphodiester linkage have been synthesized using solution phase phosphoramidite chemistry. Fmoc was used as the 5'-protecting group because of incompatibility of the cyanoborane moiety with 5'-DMT cations generated during the deprotection step. The presence of the cyanoborane group was confirmed on the basis of Fab-MS and 1H NMR spectroscopy. The H-8 proton of (7b)dG in the dinucleotides shifted 0.35-0.80 p.p.m. downfield relative to that of unmodified dG. A comparison of the D20 exchange kinetics of the H-8 proton at 60 degrees C showed that H-8 of (7b)dG is very labile relative to unmodified dG, indicating that the N7-cyanoborane modification increases the acidity of the H-8 proton of (7b)dG. These studies illustrate the feasibility of synthesizing boron-containing oligonucleotides which are modified at the N7-guanine to block Hoogsteen pairing in the DNA major groove.

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Published In

Nucleic acids research

DOI

EISSN

1362-4962

ISSN

0305-1048

Publication Date

June 1996

Volume

24

Issue

11

Start / End Page

2150 / 2157

Related Subject Headings

  • Spectrometry, Mass, Fast Atom Bombardment
  • Protons
  • Phosphoric Acids
  • Nucleotides
  • Magnetic Resonance Spectroscopy
  • Kinetics
  • Hydrogen-Ion Concentration
  • Fluorenes
  • Developmental Biology
  • Deuterium
 

Citation

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ICMJE
MLA
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Hasan, A., Li, H., Tomasz, J., & Shaw, B. R. (1996). Base-boronated dinucleotides: synthesis and effect of N7-cyanoborane substitution on the base protons. Nucleic Acids Research, 24(11), 2150–2157. https://doi.org/10.1093/nar/24.11.2150
Hasan, A., H. Li, J. Tomasz, and B. R. Shaw. “Base-boronated dinucleotides: synthesis and effect of N7-cyanoborane substitution on the base protons.Nucleic Acids Research 24, no. 11 (June 1996): 2150–57. https://doi.org/10.1093/nar/24.11.2150.
Hasan A, Li H, Tomasz J, Shaw BR. Base-boronated dinucleotides: synthesis and effect of N7-cyanoborane substitution on the base protons. Nucleic acids research. 1996 Jun;24(11):2150–7.
Hasan, A., et al. “Base-boronated dinucleotides: synthesis and effect of N7-cyanoborane substitution on the base protons.Nucleic Acids Research, vol. 24, no. 11, June 1996, pp. 2150–57. Epmc, doi:10.1093/nar/24.11.2150.
Hasan A, Li H, Tomasz J, Shaw BR. Base-boronated dinucleotides: synthesis and effect of N7-cyanoborane substitution on the base protons. Nucleic acids research. 1996 Jun;24(11):2150–2157.
Journal cover image

Published In

Nucleic acids research

DOI

EISSN

1362-4962

ISSN

0305-1048

Publication Date

June 1996

Volume

24

Issue

11

Start / End Page

2150 / 2157

Related Subject Headings

  • Spectrometry, Mass, Fast Atom Bombardment
  • Protons
  • Phosphoric Acids
  • Nucleotides
  • Magnetic Resonance Spectroscopy
  • Kinetics
  • Hydrogen-Ion Concentration
  • Fluorenes
  • Developmental Biology
  • Deuterium