Bidirectional solid phase synthesis of a model oligoglycine bolaamphiphile and purification by rapid self-assembly

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dc.contributor.authorNaidoo V.B.
dc.contributor.authorRautenbach, Marina
dc.date.accessioned2012-05-17T08:58:55Z
dc.date.available2012-05-17T08:58:55Z
dc.date.issued2012
dc.description.abstractWe utilised a simple bidirectional (N→C and C→N) solid phase synthesis strategy entailing conventional solid phase peptide synthesis and fragment condensation with a water-soluble carbodiimide to synthesise a model anionic glycylglycine bolaamphiphile containing a suberic acid linker moiety, namely N,N′-suberoyldiglycylglycine. The synthetic suberoyldiglycylglycine was purified using its inherent ability to rapidly self-assemble in an aqueous acidic solution (0.1% trifluoroacetic acid). Monitoring of the rapid assembly process corroborated our visual observation and confirmed packing-directed self-assembly rather than non-specific aggregation or precipitation. The progress of suberoyldiglycylglycine self-assembly was observed to be via the formation of oligomers in the solution, which then self-assembled to form layered β-sheet type macrostructures. Within 24h, nanotubes grew from these macrostructures and eventually combined to formed microtubes, which we isolated after 5-7days. © 2012 European Peptide Society and John Wiley & Sons, Ltd.
dc.identifier.citationJournal of Peptide Science
dc.identifier.citation18
dc.identifier.citation5
dc.identifier.citation317
dc.identifier.citation325
dc.identifier.issn10752617
dc.identifier.other10.1002/psc.2402
dc.identifier.urihttp://hdl.handle.net/10019.1/21019
dc.subjectamphophile
dc.subjectcyanamide
dc.subjectglycine derivative
dc.subjectoligomer
dc.subjecttrifluoroacetic acid
dc.subjectacidity
dc.subjectaqueous solution
dc.subjectarticle
dc.subjectbeta sheet
dc.subjectelectrospray mass spectrometry
dc.subjectmolecular model
dc.subjectprecipitation
dc.subjectpriority journal
dc.subjectprotein assembly
dc.subjectprotein structure
dc.subjectpurification
dc.subjectscanning electron microscopy
dc.subjectsolid phase synthesis
dc.titleBidirectional solid phase synthesis of a model oligoglycine bolaamphiphile and purification by rapid self-assembly
dc.typeArticle
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