3 years ago

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

Self-Assembly of Fluorinated Sugar Amino Acid Derived α,γ-Cyclic Peptides into Transmembrane Anion Transport
Sachin S. Burade, Rajesh G. Gonnade, Naresh Bhuma, Amol Kotmale, Tanmoy Saha, Dilip D. Dhavale, Pinaki Talukdar, Pattuparambil R. Rajamohanan, Navanath Kumbhar
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02942

DOI: 10.1021/acs.orglett.7b02942

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