TY - JOUR
T1 - Amphiphilic triazolyl peptides
T2 - Synthesis and evaluation as nanostructures
AU - Sayeh, Naser
AU - Shirazi, Amir N.
AU - Oh, Donghoon
AU - Sun, Jiadong
AU - Rowley, David
AU - Banerjee, Antara
AU - Yadav, Arpita
AU - Tiwari, Rakesh K.
AU - Parang, Keykavous
PY - 2014/3/1
Y1 - 2014/3/1
N2 - 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 _-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.
AB - 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 _-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.
KW - Amphiphiles
KW - Click chemistry
KW - Cyclic peptides
KW - Nanoparticles
KW - Peptides
KW - Triazole
UR - http://www.scopus.com/inward/record.url?scp=84911486057&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84911486057&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:84911486057
SN - 1385-2728
VL - 18
SP - 2665
EP - 2671
JO - Current Organic Chemistry
JF - Current Organic Chemistry
IS - 20
ER -