Title: Synthesis of DNA Duplexes Containing Site-Specific Interstrand Cross-Links via Sequential Reductive Amination Reactions Involving Diamine Linkers and Abasic Sites on Complementary Oligodeoxynucleotides.
Authors: Housh, Kurt; Gates, Kent S
Published In Chem Res Toxicol, (2021 11 15)
Abstract: 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.
PubMed ID: 34694787
MeSH Terms: Amination; Cross-Linking Reagents/chemistry*; DNA/chemical synthesis*; DNA/chemistry; Diamines/chemistry*; Molecular Structure; Oligodeoxyribonucleotides/chemistry*