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Updated: Jan 30, 2026

Imaging Denatured Collagen Strands In vivo and Ex vivo via Photo-triggered Hybridization of Caged Collagen Mimetic Peptides
Published on: January 31, 2014
γ-Azaproline Confers pH Responsiveness and Functionalizability on Collagen Triple Helices
Matthew R Aronoff1, Jasmine Egli1, Massimiliano Menichelli1
1Laboratory of Organic Chemistry, ETH Zürich, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland.
Abstract:
Proline derivatives bearing substituents at Cγ are valuable tools for biological and materials investigations. However, the stereochemistry at Cγ can produce undesired steric or stereoelectronic interactions. Here, we introduce γ-azaproline (γ-azPro), which lacks a stereogenic center at Cγ, as a pH-responsive and functionalizable proline analogue that can adapt to its environment. Conformational analyses by NMR spectroscopy and DFT calculations revealed that the imidazolidine ring of γ-azPro is flexible. Incorporation of γ-azPro into collagen model peptides (CMPs) produced pH-responsive triples helices and triple helices that can be easily functionalized.
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