Hydrogen-bonded DeUG x DAN heterocomplex: structure and stability and a scalable synthesis of DeUG with reactive functionality.
نویسندگان
چکیده
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 x DAN heterocomplex were obtained. K(assoc) for the 1.2 heterocomplex was estimated to be 2 x 10(8) M(-1) in chloroform.
منابع مشابه
Higher affinity quadruply hydrogen-bonded complexation with 7-deazaguanine urea.
[structure: see text] 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 (K(assoc) approximately 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...
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عنوان ژورنال:
- Organic letters
دوره 11 1 شماره
صفحات -
تاریخ انتشار 2009