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

Research output: Contribution to journalArticle

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 languageEnglish (US)
Pages (from-to)61-64
Number of pages4
JournalOrganic Letters
Volume11
Issue number1
DOIs
StatePublished - Jan 1 2009

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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