Amphiphilic Triazolyl Peptides: Synthesis and Evaluation as Nanostructures

Title:Amphiphilic Triazolyl Peptides: Synthesis and Evaluation as Nanostructures

Volume: 18 Issue: 20

Author(s): Naser Sayeh, Amir N. Shirazi, Donghoon Oh, Jiadong Sun, David Rowley, Antara Banerjee, Arpita Yadav, Rakesh K. Tiwari and Keykavous Parang

Affiliation:

Keywords: Amphiphiles, click chemistry, cyclic peptides, nanoparticles, peptides, triazole.

Abstract: A new class of amphiphilic triazolyl peptides was designed and synthesized from peptide-based building blocks containing alkyne and azide functional groups namely linear (W(pG))₃, cyclic[W(pG)]₃, and Ac-K(N₃)R-NH₂,where W, R, K, and pG represent tryptophan, arginine, lysine, and propargylglycine residues, respectively. The linear (W(pG))₃ and cyclic [W(pG)]₃ peptides containing alkyne residues were conjugated with Ac-K(N₃)R-NH₂ functionalized with azide group through click chemistry in the presence of CuSO₄.5H₂O, Cu (powder), sodium ascorbate, and N,N-disopropylethylamine in methanol:water to afford amphiphilic triazolyl linear-linear (WG(triazole-KR-NH₂))₃ and cyclic-linear [WG(triazole-KR-NH₂)]₃ peptides, respectively. The secondary structures of both peptides were similar to a distorted α-helix as shown by CD spectroscopy. TEM imaging showed that linear-linear (WG(triazole-KR-NH₂))₃ and cyclic-linear [WG(triazole-KR-NH₂)]₃ peptides formed nano-sized structures in the size range of 50-100 nm and 50-80 nm, respectively.

Cite this article as:

Sayeh Naser, Shirazi N. Amir, Oh Donghoon, Sun Jiadong, Rowley David, Banerjee Antara, Yadav Arpita, Tiwari K. Rakesh and Parang Keykavous, Amphiphilic Triazolyl Peptides: Synthesis and Evaluation as Nanostructures, Current Organic Chemistry 2014; 18 (20) . https://dx.doi.org/10.2174/138527281820141028110625