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. 2009 Oct 7:(37):5588-90.
doi: 10.1039/b912094g. Epub 2009 Aug 13.

Facile synthesis of stapled, structurally reinforced peptide helices via a photoinduced intramolecular 1,3-dipolar cycloaddition reaction

Michael M Madden  1 , Claudia I Rivera Vera, Wenjiao Song, Qing Lin
Affiliations

Facile synthesis of stapled, structurally reinforced peptide helices via a photoinduced intramolecular 1,3-dipolar cycloaddition reaction

Michael M Madden et al. Chem Commun (Camb). .

Abstract

We report the first use of a photoinduced 1,3-dipolar cycloaddition reaction in "stapling" peptide sidechains to reinforce a model peptide helical structure with moderate to excellent yields; the resulting pyrazoline "staplers" exhibit unique fluorescence useful in a cell permeability study.

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Figures

Fig. 1
Fig. 1
(a) CD spectra of the stapled peptides 9-16 and the linear peptide 17 at 25 °C. Peptides were dissolved in TFE to derive 100 μM solutions. The calculated percent helicity values were listed in the table. (b) Thermal melting curves of peptides 16 and 17. 100 μM peptide solutions in 20% TFE/H2O were used in the CD scans.
Fig. 2
Fig. 2
UV-Vis and fluorescence spectra of the stapled peptides: (a) 9; (b) 10; (c) 11; (d) 12; (e) 13; (f) 14; (g) 15; (h) 16. Dashed lines represent the UV absorbance spectra while solid lines represent the fluorescence emission spectra. The absorption and emission maxima were marked on top of the spectra.
Fig. 3
Fig. 3
Fluorescent images of fixed HeLa cells overlaid on the DIC images after treatment of 100 μM of (a) peptide 13 or (b) linear control peptide 18.
See this image and copyright information in PMC

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