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

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posted on 2017-10-23, 13:06 authored by Sachin S. Burade, Tanmoy Saha, Naresh Bhuma, Navanath Kumbhar, Amol Kotmale, Pattuparambil R. Rajamohanan, Rajesh G. Gonnade, Pinaki Talukdar, Dilip D. Dhavale
Syntheses of fluorinated sugar amino acid derived α,γ-cyclic tetra- and hexapeptides are reported. The IR, NMR, ESI-MS, CD, and molecular modeling studies of cyclic tetra- and hexapeptides showed C2 and C3 symmetric flat oval- and triangular-ring shaped β-strand conformations, respectively, which appear to self-assemble into nanotubes. The α,γ-cyclic hexapeptide (EC50 = 2.14 μM) is found to be a more efficient ion transporter than α,γ-cyclic tetrapeptide (EC50 = 14.75 μM). The anion selectivity and recognition of α,γ-cyclic hexapeptide with NO3 ion is investigated.