Determination of the Tautomeric Equlibrium of ψ-Uridine in the Basic Solution

I. Luyten, K. W. Pankiewicz, K. A. Watanabe, J. Chattopadhyaya

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The pD-dependent 13C shift and 3JCH of ψ-uridine have shown that the pKa of its N1 and N3 are 9.6 and 9.3, respectively. For the monoanionic ψ-uridine, the N1-anion population (64%) is favored over the N3-anion (36%), suggesting a larger preference of the population for N1-Hg2+ complex for ψ-uridine over its N3-Hg2+ complex in the neutral pH, which has also been proven by the similarity of the pD-dependent titration curve of ψ-uridine and its N3-methyl-ψ-uridine. Finally, ab initio molecular orbital calculations with a 6-31G** basis set (Gaussian 94) have been used to explain why the Nl-anion tautomer of ψ-uridine is thermodynamically more stable than the N3-anion tautomer of ψ-uridine, which cannot be corroborated by the results of the calculations at 6-31+G** and 6-31++G** levels. The fact that N1 of ψ-uridine (pKa 9.3) is more acidic than N3 (pKa 9.6) implies that the N1-H will compete favorably for any potential hydrogen bonding with a complementary nucleotide over the N3-H.

Original languageEnglish (US)
Pages (from-to)1033-1040
Number of pages8
JournalJournal of Organic Chemistry
Issue number4
StatePublished - Feb 20 1998
Externally publishedYes


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