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

DC FieldValueLanguage
dc.contributor.authorSeela, Frank
dc.contributor.authorPujari, Suresh S.
dc.contributor.authorSchaefer, Andreas H.
dc.date.accessioned2021-12-23T16:07:55Z-
dc.date.available2021-12-23T16:07:55Z-
dc.date.issued2011
dc.identifier.issn00404020
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/8136-
dc.description.abstractNucleoside 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. (C) 2011 Elsevier Ltd. All rights reserved.
dc.description.sponsorshipChemBiotech, Muenster, Germany; We are especially grateful to P. Ding for the synthesis, characterization and supply of the 7-deazapurine click conjugate 13. We would like to thank Dr. S. Budow and Dr. P. Leonard for helpful discussions and support. We also thank S.A. Ingale for reading of the manuscript. Financial support by ChemBiotech, Muenster, Germany, is highly appreciated.
dc.language.isoen
dc.publisherPERGAMON-ELSEVIER SCIENCE LTD
dc.relation.ispartofTETRAHEDRON
dc.subject`Click' conjugates
dc.subjectAZIDE
dc.subjectChemistry
dc.subjectChemistry, Organic
dc.subjectGELATION ABILITY
dc.subjectGELATORS
dc.subjectGUANOSINE
dc.subjectHELIX FORMATION
dc.subjectHydrogelation
dc.subjectModified nucleosides
dc.subjectORGANOGELS
dc.subjectPyrazolo[3,4-d]pyrimidines
dc.subjectWATER GELATION
dc.titleHydrogelation and spontaneous fiber formation of 8-aza-7-deazaadenine nucleoside `click' conjugates
dc.typejournal article
dc.identifier.doi10.1016/j.tet.2011.07.015
dc.identifier.isiISI:000294593400032
dc.description.volume67
dc.description.issue38
dc.description.startpage7418
dc.description.endpage7425
dc.contributor.orcid0000-0002-0246-3362
dc.publisher.placeTHE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
dcterms.isPartOf.abbreviationTetrahedron
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