Bidirectional solid phase synthesis of a model oligoglycine bolaamphiphile and purification by rapid self-assembly
Date
2012
Authors
Naidoo V.B.
Rautenbach, Marina
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Abstract
We 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.
Description
Keywords
amphophile, cyanamide, glycine derivative, oligomer, trifluoroacetic acid, acidity, aqueous solution, article, beta sheet, electrospray mass spectrometry, molecular model, precipitation, priority journal, protein assembly, protein structure, purification, scanning electron microscopy, solid phase synthesis
Citation
Journal of Peptide Science
18
5
317
325
18
5
317
325