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The pseudopeptide Gly-m-ABA (m-ABA = m-amino benzoic acid) has been chosen to study the formation of supramolecular structures through self-assembly. Single crystal X-ray diffraction studies reveal that the pseudopeptide Boc-Gly-m-ABA-OMe (1), where both N- and C-terminus are protected, self-assembles to a supramolecular helical structure, whereas the pseudopeptide Boc-Gly-m-ABA-OH (2) with free –CO2H at the C-terminus produces molecular staircase through self-assembly. Again the terminally unprotected pseudopeptide + NH3-Gly-m-ABA-CO2 (3) aggregates to a water mediated supramolecular β-sheet structure stabilized by intermolecular hydrogen bonds and π-π interactions. The study reveals that the terminally modified Gly-m-ABA generates various kinds of self-assembling building blocks that can fabricate different types of supramolecular architectures such as helix, β-sheet and staircase.

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A terminally modified pseudopeptide (Gly-m-aminobenzoic acid) produces supramolecular helix, staircase and water-mediated β-sheet through self-assembly