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γ‐Azaproline Confers pH Responsiveness and Functionalizability on Collagen Triple Helices
Author(s) -
Aronoff Matthew R.,
Egli Jasmine,
Menichelli Massimiliano,
Wennemers Helma
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201813048
Subject(s) - stereocenter , steric effects , imidazolidine , chemistry , proline , triple helix , stereochemistry , ring (chemistry) , nuclear magnetic resonance spectroscopy , amino acid , combinatorial chemistry , catalysis , enantioselective synthesis , organic chemistry , biochemistry
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.