title: Bidirectional solid phase synthesis of a model oligoglycine bolaamphiphile and purification by rapid self-assembly.
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 24 h, nanotubes grew from these macrostructures and eventually combined to formed microtubes, which we isolated after 5-7 days.
authors.affiliation: UNESCO Associated Centre for Macromolecules and Materials, Division of Polymer Science, Department of Chemistry, University of Stellenbosch, Private Bag X1, Matieland, 7600, South Africa.
authors.forename: Venthan B
authors.initials: VB
authors.lastname: Naidoo
authors.forename: Marina
authors.initials: M
authors.lastname: Rautenbach
mesh_terms: D005663:Furans / Q000737:chemistry*; D008855:Microscopy, Electron, Scanning; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D011728:Pyridones / Q000737:chemistry*; D060327:Solid-Phase Synthesis Techniques / Q000379:methods*; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D005663:Furans; D009842:Oligopeptides; D011728:Pyridones; C543575:bolaamphiphile