Site-specific cross-linking of nucleic acids using the abasic site.
[formula: see text] An efficient site-specific cross-linking reaction between two carbohydrate residues present in two complementary DNA sequences is described. One oligodeoxynucleotide, 5'd(GGCTGA*CTGCG)3', carries an amino nucleophile tethered to the 2'-hydroxyl of an adenosine residue (A*). The target electrophile is an abasic site generated in the complementary sequence, 5'd(CGCAGDCAGCC)3' (D represents the deoxyribose). The cross-linking reaction was carried out by a reductive amination reaction in > 95% yield.
Manoharan
M
M
Department of Medicinal Chemistry, Isis Pharmaceuticals. mmanoharan@isisph.com
Andrade
L K
LK
Cook
P D
PD
D000241:Adenosine / Q000737:chemistry; D000586:Amination; D003432:Cross-Linking Reagents / Q000737:chemistry*; D018076:DNA, Complementary / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009696:Nucleic Acids / Q000737:chemistry*; D010084:Oxidation-Reduction
D003432:Cross-Linking Reagents; D018076:DNA, Complementary; D009696:Nucleic Acids; D000241:Adenosine