Abstract
UG forms a highly stable quadruply hydrogen-bonded heterocomplex with DAN, but the fidelity of the complex is lowered somewhat by the Hoogsteen-side oligomerization of UG (Kassoc ∼ 230 M-1, CDCl 3). DeUG was prepared as a more robust analogue of UG lacking the Hoogsteen nitrogen atom. Remarkably, the deaza analogue, DeUG, forms a much more stable complex with DAN (>10-fold higher Kassoc for DeUG-DAN vs UG-DAN) but also dimerizes more strongly (Kdim = 880 ± 40 M-1, CDCl3) by adopting a conformation preorganized for both binding and dimerization.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1589-1592 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 8 |
| Issue number | 8 |
| DOIs | |
| State | Published - Apr 13 2006 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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