期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 10, 页码 3143-3146出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201813048
关键词
amides; collagen; isomerization; pH responsiveness; proline
资金
- ETH Zurich
- European Union
- Swiss National Science Foundation [200020_178805]
- Swiss National Science Foundation (SNF) [200020_178805] Funding Source: Swiss National Science Foundation (SNF)
Proline derivatives bearing substituents at C gamma are valuable tools for biological and materials investigations. However, the stereochemistry at C gamma can produce undesired steric or stereoelectronic interactions. Here, we introduce gamma-azaproline (gamma-azPro), which lacks a stereogenic center at C gamma, 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 gamma-azPro is flexible. Incorporation of gamma-azPro into collagen model peptides (CMPs) produced pH-responsive triples helices and triple helices that can be easily functionalized.
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