Self-Assembly of Fluorinated Sugar Amino Acid Derived α,γ-Cyclic Peptides into Transmembrane Anion Transport

Syntheses of fluorinated sugar amino acid derived <i>α</i>,<i>γ</i>-cyclic tetra- and hexapeptides are reported. The IR, NMR, ESI-MS, CD, and molecular modeling studies of cyclic tetra- and hexapeptides showed <i>C</i>₂ and <i>C</i>₃ symmetric flat oval- and triangular-ring shaped β-strand conformations, respectively, which appear to self-assemble into nanotubes. The <i>α,γ</i>-cyclic hexapeptide (<i>EC</i>₅₀ = 2.14 μM) is found to be a more efficient ion transporter than <i>α</i>,<i>γ</i>-cyclic tetrapeptide (<i>EC</i>₅₀ = 14.75 μM). The anion selectivity and recognition of <i>α</i>,<i>γ</i>-cyclic hexapeptide with NO₃^– ion is investigated

Self-Assembly of Fluorinated Sugar Amino Acid Derived α,γ-Cyclic Peptides into Transmembrane Anion Transport

Syntheses of fluorinated sugar amino acid derived <i>α</i>,<i>γ</i>-cyclic tetra- and hexapeptides are reported. The IR, NMR, ESI-MS, CD, and molecular modeling studies of cyclic tetra- and hexapeptides showed <i>C</i>₂ and <i>C</i>₃ symmetric flat oval- and triangular-ring shaped β-strand conformations, respectively, which appear to self-assemble into nanotubes. The <i>α,γ</i>-cyclic hexapeptide (<i>EC</i>₅₀ = 2.14 μM) is found to be a more efficient ion transporter than <i>α</i>,<i>γ</i>-cyclic tetrapeptide (<i>EC</i>₅₀ = 14.75 μM). The anion selectivity and recognition of <i>α</i>,<i>γ</i>-cyclic hexapeptide with NO₃^– ion is investigated