Hydrogen-bonded deugdan heterocomplex: Structure and stability and a scalable synthesis of DeUG with reactive functionality

Darrell W. Kuykendall; Cyrus A. Anderson; Steven C. Zimmerman

doi:10.1021/ol802344w

Hydrogen-bonded deugdan heterocomplex: Structure and stability and a scalable synthesis of DeUG with reactive functionality

Darrell W. Kuykendall, Cyrus A. Anderson, Steven C. Zimmerman

Chemistry

Research output: Contribution to journal › Article › peer-review

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	https://doi.org/10.1021/ol802344w
State	Published - Jan 1 2009

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol802344w

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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.",

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AU - Zimmerman, Steven C.

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AB - 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.

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Hydrogen-bonded deugdan heterocomplex: Structure and stability and a scalable synthesis of DeUG with reactive functionality

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