Abstract
A convenient, scalable synthesis of the supramolecular building block 7-deazaguanine-based urea (DeUG) is reported. Incorporation of reactive moieties (DeUG azide 10 and alkyne 11 for copper-catalyzed azide-alkyne cycloadditions, "click chemistry") and a demonstration of transesterification (DeUG glycol, 12) highlights the versatility. X-ray structures of DeUG and a DeUG-DAN heterocomplex were obtained. K assoc for the 1.2 heterocomplex was estimated to be 2 x 10 8 M -1 in chloroform.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 61-64 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 11 |
| Issue number | 1 |
| DOIs | |
| State | Published - Jan 1 2009 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Kuykendall, D. W., Anderson, C. A., & Zimmerman, S. C. (2009). Hydrogen-bonded deugdan heterocomplex: Structure and stability and a scalable synthesis of DeUG with reactive functionality. Organic Letters, 11(1), 61-64. https://doi.org/10.1021/ol802344w