Sequence-specific alkylation of double-helical DNA by oligonucleotide-directed triple-helix formation

Journal Article · Wed Dec 05 04:00:00 EST 1990 · Journal of the American Chemical Society; (United States)

DOI:https://doi.org/10.1021/ja00181a075· OSTI ID:5967116

Povsic, T J; Dervan, P B ^[1]

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1. California Inst. of Tech., Pasadena (United States)

Affinity cleaving, a method that relies on the attachment of a nonspecific cleaving moiety, such as EDTA{center dot}Fe(II), to a DNA binding molecule, facilitates the elucidation of the structural principles for DNA recognition. The determination of the sequence specificities, groove locations, and binding orientations of peptide analogues, protein-DNA binding motifs, and oligonucleotide-triple-helix motifs has provided reliable models for the sequence-specific recognition of double-helical DNA. It now becomes possible to combine these binding molecules with domains capable of base-specific and quantitative modification of DNA. The authors report the design and synthesis of an oligodeoxyribonucleotide equipped with an electrophile at the 5{prime}-end that binds to double-helical DNA by triple-helix formation and alkylates predominantly at a single guanine base adjacent to the target DNA sequence in high yield.

• OSTI ID: 5967116
• Journal Information: Journal of the American Chemical Society; (United States), Journal Name: Journal of the American Chemical Society; (United States) Vol. 112:25; ISSN 0002-7863; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

550200* -- Biochemistry
59 BASIC BIOLOGICAL SCIENCES
ALKYLATION
AMINES
AROMATICS
AZAARENES
AZINES
CHEMICAL REACTIONS
DNA
ELECTROPHORESIS
GUANINE
HETEROCYCLIC COMPOUNDS
HYDROXY COMPOUNDS
IMAGES
NUCLEIC ACIDS
NUCLEOSIDES
NUCLEOTIDES
OLIGONUCLEOTIDES
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PURINES
PYRIMIDINES
RIBOSIDES
THYMIDINE