A single carbocyclic nucleotide substitution in a 12mer DNA gives a Hoogsteen basepaired duplex (till 38 degrees C) and a hairpin (till 65 degrees C). A 600 MHz NMR spectroscopic study.
The impact of intramolecular stereoelectronic effects has been examined by comparison of the solution structures of natural oligo-DNA duplex, 5'(1C2G3C4G5A6A7T8T9C10G11C12G)2(3'), and its carbocyclic-nucleotide analogues in which the pentose sugar in 2'-dA residue is replaced with its carbocyclic counterpart (i.e. 2'-deoxyaristeromycin). Based on the NMR evidences, it has been shown, that 2'-deoxyaristeromycin analog exists in a dynamic equilibrium between the two forms of duplexes, one with W-C bp and the second with Hoogsteen bp in ca 1:1 ratio at lower temperature (below 35 degrees C) and as hairpin at higher temperature (from approximately 40 degrees-60 degrees C).
Isaksson
J
J
Department of Bioorganic Chemistry, Uppsala University, Sweden. jyoti@bioorgchem.uu.se
Maltseva
T
T
Agback
P
P
Luo
X
X
Kumar
A
A
Zamaratski
E
E
Chattopadhyaya
J
J
D020029:Base Pairing; D004247:DNA / Q000737:chemistry*; D006358:Hot Temperature; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009690:Nucleic Acid Conformation
D004247:DNA