4.5 Article

Synthesis of DNA Duplexes Containing Site-Specific Interstrand Cross-Links via Sequential Reductive Amination Reactions Involving Diamine Linkers and Abasic Sites on Complementary Oligodeoxynucleotides

Journal

CHEMICAL RESEARCH IN TOXICOLOGY
Volume 34, Issue 11, Pages 2384-2391

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.chemrestox.1c00293

Keywords

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Funding

  1. National Institutes of Health [ES021007]
  2. National Science Foundation [NSF-CHE 1808672]

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Interstrand DNA cross-links play important roles in biology, medicinal chemistry, and materials science. A simple procedure for preparing DNA duplexes containing site-specific, chemically defined interstrand cross-links is reported in this study. Sequential reductive amination reactions between diamine linkers and abasic sites on complementary oligodeoxynucleotides were used to achieve this.
Interstrand DNA cross-links are important in biology, medicinal chemistry, and materials science. Accordingly, methods for the targeted installation of interstrand cross-links in DNA duplexes may be useful in diverse fields. Here, a simple procedure is reported for the preparation of DNA duplexes containing site-specific, chemically defined interstrand cross-links. The approach involves sequential reductive amination reactions between diamine linkers and two abasic (apurinic/apyrimidinic, AP) sites on complementary oligodeoxynucleotides. Use of the symmetrical triamine, tris(2-aminoethyl)amine, in this reaction sequence enabled the preparation of a cross-linked DNA duplex bearing a derivatizable aminoethyl group.

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