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September 29, 2011 |
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Frank Rossi
SUNY Cortland, Department of Chemistry
Cortland, NY
“Click/Unclick”: A Modular Synthesis of
Photocleavable Peptide Conjugates
Photocleavable groups allow for the experimental alteration of biological and chemical activity with spatial and temporal control. Unfortunately, simple, modular methods for the synthesis of photocleavable bioactive peptides are lacking. We have developed a novel alkyne that serves as a traceless photocleavable linker for the modular preparation of peptides by copper catalyzed "click chemistry". The linker is prepared in two high-yielding steps from commercially available starting materials and can be reacted with amines to give urethanes. Solid phase peptide synthesis was used to attach the linker to the amino terminus of several bioactive peptides and the resulting compounds were conjugated to azide-modified peptides using click chemistry. The linked peptides were "unclicked" upon exposure to UV-light.
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