Amphiphilic Triazolyl Peptides: Synthesis and Evaluation as Nanostructures

作者：Sayeh Naser; Shirazi Amir N; Oh Donghoon; Sun Jiadong; Rowley David; Banerjee Antara; Yadav Arpita; Tiwari Rakesh K^*; Parang Keykavous

来源：Current Organic Chemistry, 2014, 18(20): 2665-2671.

DOI：10.2174/138527281820141028110625

• Amphiphiles
• click chemistry
• cyclic peptides
• nanoparticles
• peptides
• triazole

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(N-3)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(N-3)R-NH2 functionalized with azide group through click chemistry in the presence of CuSO4.5H(2)O, 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 alpha-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.

• 出版日期2014