A molecular model has been synthesized to determine the hydrogen- bonding strength between AT and T in the base triplet, T:AT. A strong preference (>95%) of Watson-Crick mode along with 91% hydrogen-bonded conformation is observed in the model compound. The association constants of the AT model with 1-propyluracil and glutarimide are 15 M-1 and 5.2 M-1, respectively, in CDCl3 at 296 ± 0.5 K. Negative cooperativity by pre- existing hydrogen bonds might be involved in the intermolecular binding events.
Bibliographical noteFunding Information:
This work was financially supported in part by the Korea Science and Engineering
Foundation (Project No, 96-0501-04-01-03) and by the Organic Chemistry Research Center-KOSEF.
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry