Synthesis of 5-substituted [N3-15N]-pyrimidine nucleosides: Developing model systems for NMR studies of substituent effects on the N-H...N hydrogen bond in duplex DNA.
The effects on various NMR parameters of substitutions, which may influence the hydrogen bond strengths of Watson-Crick-type base pairs, were investigated for DNA dodecamers containing 5-substituted-2'-deoxyuridine derivatives in oligomers, 5'-d(CGCGAATXCGCG)-3', where A and X were [ul-15N]-2'-deoxyadenosine and [3(-15)N]-2'-deoxyuridine derivatives. The substitution effects on the NMR parameters were linearly correlated with the pKa values of the 2'-deoxyuridine derivatives.
Ishikawa
R
R
Department of Chemistry, CREST, Graduate School of Science, Tokyo Metropolitan University, Tokyo, Japan.
Kojima
C
C
Ono
A
A
Kainosho
M
M
D001483:Base Sequence; D004247:DNA / Q000737:chemistry*; D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000737:chemistry; D006860:Hydrogen Bonding; D008956:Models, Chemical; D019906:Nuclear Magnetic Resonance, Biomolecular; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis / Q000737:chemistry; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry
D009838:Oligodeoxyribonucleotides; D011741:Pyrimidine Nucleosides; D004247:DNA; D003857:Deoxyuridine