Solution structure of a DNA duplex containing a formamide-adenine base pair.
The N-(2-deoxy-beta3-D-erythro-pentofuranosyl) formamide residue results from a ring fragmentation product of thymine or cytosine. The presence of a formamide-adenine base pair in the sequence 5'd(AGGAACCACG).d(CGTGGFTCCT) has been studied by 1H and 31P nuclear magnetic resonance (NMR) and molecular dynamics. There are two possible isomers for the formamide side chain, either cis or trans. For each isomer, we observed an equilibrium in solution between two forms. First, a species where the formamide is intrahelical and paired with the facing adenine. For the cis isomer, the formamide is in a syn conformation and two hydrogen bonds with adenine are formed. The trans isomer is in an anti conformation and a single hydrogen bond is observed. In the second form, whatever the isomer, the formamide is rejected outside the helix, whereas the adenine remains inside.
Maufrais
Corinne
C
CEA Saclay, Service de Biochimie et de Génétique Moléculaire, Gif-sur-Yvette, France.
Boulard
Yves
Y
D000225:Adenine / Q000737:chemistry*; D020029:Base Pairing; D004247:DNA / Q000138:chemical synthesis / Q000737:chemistry*; D005559:Formamides / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009690:Nucleic Acid Conformation; D011522:Protons
D005559:Formamides; D011522:Protons; D004247:DNA; D000225:Adenine