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Hydrogen bonding in complexes of adenosine and 4-thiouridine: a low-temperature NMR study

โœ Scribed by Eline M. Basilio Janke; Anita Dunger; Hans-Heinrich Limbach; Klaus Weisz

Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
142 KB
Volume
39
Category
Article
ISSN
0749-1581

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โœฆ Synopsis

NMR experiments were performed on the association of the two sugar-protected nucleosides 2 -deoxy-4-thiouridine and 2 -deoxyadenosine in solution. Using an aprotic CDClF 2 -CDF 3 solvent mixture, low-temperature measurements allowed the observation of individual hydrogen-bonded complexes in the slow exchange regime. 2D NOE experiments acquired at 128 K show the preferential formation of a ternary complex with two thiouridine nucleosides simultaneously bound at the Watson-Crick and Hoogsteen site of adenosine at all molar ratios. There is no indication of the 4-thiocarbonyl group involved as proton acceptor in a hydrogen bond to the adenine base to a significant extent. A more downfield chemical shift together with a smaller 1 J.N, H/ scalar coupling of the Watson-Crick-bound imino proton in specifically 3-15 N-labeled thiouridine points to a stronger Watson-Crick than the Hoogsteen hydrogen bond.

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