Active ion transporters from readily accessible acyclic octapeptides containing 3-aminobenzoic acid and alanine

Abstract

Ion transporters have been developed from acyclic octapeptides comprising L/D alanine and m-aminobenzoic acid. These octapeptides transport cations up to 3 times faster than their cyclic analog through lipid vesicles. Preliminary CD, XRD and computational studies allude to a 6-9 Å wide tetrameric ion channel as the active ion transporter.

Aminobenzoic acid incorporated octapeptides for cation transport

“…Microscopy studies with peptide 1 also showed that it self-assembles to form nanotubes. 20 The TEM image of octapeptide 2 indicated that it also self-assembles to form bundles of nanotubes (Fig. 5).…”

“…Octapeptide 1 was synthesized as reported earlier. 20 Peptide 2 was synthesized in solution as outlined in Scheme 1. Peptides 3-5 were also synthesized in solution, following a slightly modified synthetic route.…”

“…We have recently demonstrated that acyclic octapeptides synthesized from L/D alanine and m-aminobenzoic acid (ABA) transport ions across the lipid bilayer more efficiently than their cyclic analog. 20 Herein, we report the ion transport activity of octapeptides incorporated with aromatic aminobenzoic acid units (Fig. 1).…”

Low Molecular Weight Di‐ to Tetrapeptide Transmembrane Cation Transporters

“…We have previously reported octapeptides and amphiphilic tetrapeptides for cation transport (Figure 1b). [ 20 ]…”

Sugar Derived Oxazolone Pseudotetrapeptide as γ-Turn Inducer and Anion-Selective Transporter

“…Anydysfunction in these processes led to various diseases such as cystic fibrosis, Dent disease, Bartter syndrome, and epilepsy [34][35][36][37][38][39][40][41]. In order to mimic the regulatory functions in living systems, a wide range of anion transporters have been investigated that include peptides [42][43][44][45][46][47][48][49][50][51], oligoureas [52][53], anion-π slides [54][55][56][57],steroids [58][59][60][61], calixpyrroles [62][63][64],calixarenes [65][66][67], and other scaffolds [68][69][70]. In particular, peptide based transmembrane anion transporters have attracted great interest.…”