Hydrogelation and spontaneous fiber formation of 8-aza-7-deazaadenine nucleoside 'click' conjugates

Frank Seela, Suresh S. Pujari, Andreas H. Schäfer

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

Nucleoside hydrogels based on benzyl azide 'click' conjugates of 8-aza-7-deaza-2′-deoxyadenosine bearing 7-ethynyl, 7-octa-(1,7-diynyl), and 7-tri-prop-2-ynyl-amine side chains were synthesized (1, 3, 4). The cycloaddition adduct with the shortest linker (1) yields the most powerful hydrogelator forming stable gels at a concentration of 0.3 wt % of 1 in water. One molecule of 1 catches 7500 water molecules. Cycloaddition of the 8-aza-7-deaza-7-azido-2′-deoxyadenosine (9) and 3-phenyl-1-propyne (10) leads to the isomeric conjugate 2, with a C-N connectivity between the nucleobase and triazole moiety. This gel is less stable than that of the adduct 1. Both gels show a similar stability over a wide pH range (4.0-10.0). Xerogels of 1 and 2 studied by scanning electron microscopy (SEM) reveal that both click adducts (1 and 2) form long fibers spontaneously.

Original languageEnglish (US)
Pages (from-to)7418-7425
Number of pages8
JournalTetrahedron
Volume67
Issue number38
DOIs
StatePublished - Sep 23 2011

Keywords

  • 'Click' conjugates
  • Hydrogelation
  • Modified nucleosides
  • Pyrazolo[3,4-d] pyrimidines

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