AI Article Synopsis
- Proline derivatives with Cγ substituents are useful in biological and materials research, but their stereochemistry can cause unwanted interactions.
- γ-azaproline (γ-azPro) is introduced as a new proline analogue that is pH-responsive and can be modified, without a stereogenic center at Cγ.
- Studies show that γ-azPro has a flexible imidazolidine ring, and when included in collagen model peptides (CMPs), it creates pH-responsive triple helices that can be easily functionalized.
Article 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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| http://dx.doi.org/10.1002/anie.201813048 | DOI Listing |
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