Facile synthesis of stapled, structurally reinforced peptide helices via a photoinduced intramolecular 1,3-dipolar cycloaddition reaction
- 13 August 2009
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 37,p. 5588-5590
- https://doi.org/10.1039/b912094g
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.Keywords
This publication has 34 references indexed in Scilit:
- Fast Alkene Functionalization In Vivo by Photoclick Chemistry: HOMO Lifting of Nitrile Imine DipolesAngewandte Chemie International Edition in English, 2009
- Selective Functionalization of a Genetically Encoded Alkene-Containing Protein via “Photoclick Chemistry” in Bacterial CellsJournal of the American Chemical Society, 2008
- Sequence‐Based Design of α/β‐Peptide Foldamers That Mimic BH3 DomainsAngewandte Chemie International Edition in English, 2008
- A Domino Sequence Consisting of Insertion, Coupling, Isomerization, and Diels–Alder Steps Yields Highly Fluorescent SpirocyclesAngewandte Chemie International Edition in English, 2004
- Activation of Apoptosis in Vivo by a Hydrocarbon-Stapled BH3 HelixScience, 2004
- Effective stabilisation of α-helical structures in short peptides with acetylenic cross-linking agentsChemical Communications, 2004
- Aib-Rich Peptides Containing Lactam-Bridged Side Chains as Models of the 310-HelixJournal of the American Chemical Society, 2001
- Structure of Bcl-x L -Bak Peptide Complex: Recognition Between Regulators of ApoptosisScience, 1997
- The Structure and Energetics of Helix Formation by Short Templated Peptides in Aqueous Solution. 2. Characterization of the Helical Structure of Ac-Hel1-Ala6-OHJournal of the American Chemical Society, 1996
- Circular Dichroism Spectrum of a Peptide 310-HelixJournal of the American Chemical Society, 1996