Issue 37, 2009
From the journal:

Chemical Communications

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

Michael M. Madden,a   Claudia I. Rivera Vera,a   Wenjiao Songa  and  Qing Lin*a  

* Corresponding authors

a Department of Chemistry, State University of New York at Buffalo, Buffalo, New York 14260, USA
E-mail: qinglin@ buffalo.edu
Fax: +1 (716) 645 6963
Tel: +1 (716) 645 4254

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.

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

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Article information

DOI
https://doi.org/10.1039/B912094G
Article type
Communication
Submitted
22 Jun 2009
Accepted
23 Jul 2009
First published
13 Aug 2009

Chem. Commun., 2009, 5588-5590

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

M. M. Madden, C. I. Rivera Vera, W. Song and Q. Lin, Chem. Commun., 2009, 5588 DOI: 10.1039/B912094G

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