Amphiphilic triazolyl peptides: Synthesis and evaluation as nanostructures

Naser Sayeh, Amir N. Shirazi, Donghoon Oh, Jiadong Sun, David Rowley, Antara Banerjee, Arpita Yadav, Rakesh K. Tiwari, Keykavous Parang

Research output: Contribution to journalArticle

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 _-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.

Original languageEnglish (US)
Pages (from-to)2665-2671
Number of pages7
JournalCurrent Organic Chemistry
Volume18
Issue number20
StatePublished - Mar 1 2014
Externally publishedYes

Fingerprint

Nanostructures
Triazoles
Peptides
Alkynes
Azides
Tryptophan
Powders
Functional groups
Ascorbic Acid
Lysine
Methanol
Arginine
Spectroscopy
Transmission electron microscopy
Imaging techniques
Water

Keywords

  • Amphiphiles
  • Click chemistry
  • Cyclic peptides
  • Nanoparticles
  • Peptides
  • Triazole

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Sayeh, N., Shirazi, A. N., Oh, D., Sun, J., Rowley, D., Banerjee, A., ... Parang, K. (2014). Amphiphilic triazolyl peptides: Synthesis and evaluation as nanostructures. Current Organic Chemistry, 18(20), 2665-2671.

Amphiphilic triazolyl peptides : Synthesis and evaluation as nanostructures. / Sayeh, Naser; Shirazi, Amir N.; Oh, Donghoon; Sun, Jiadong; Rowley, David; Banerjee, Antara; Yadav, Arpita; Tiwari, Rakesh K.; Parang, Keykavous.

In: Current Organic Chemistry, Vol. 18, No. 20, 01.03.2014, p. 2665-2671.

Research output: Contribution to journalArticle

Sayeh, N, Shirazi, AN, Oh, D, Sun, J, Rowley, D, Banerjee, A, Yadav, A, Tiwari, RK & Parang, K 2014, 'Amphiphilic triazolyl peptides: Synthesis and evaluation as nanostructures', Current Organic Chemistry, vol. 18, no. 20, pp. 2665-2671.
Sayeh N, Shirazi AN, Oh D, Sun J, Rowley D, Banerjee A et al. Amphiphilic triazolyl peptides: Synthesis and evaluation as nanostructures. Current Organic Chemistry. 2014 Mar 1;18(20):2665-2671.
Sayeh, Naser ; Shirazi, Amir N. ; Oh, Donghoon ; Sun, Jiadong ; Rowley, David ; Banerjee, Antara ; Yadav, Arpita ; Tiwari, Rakesh K. ; Parang, Keykavous. / Amphiphilic triazolyl peptides : Synthesis and evaluation as nanostructures. In: Current Organic Chemistry. 2014 ; Vol. 18, No. 20. pp. 2665-2671.
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