Inviting Trifluoromethylated Pseudoprolines into Collagen Model Peptides

01 September 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Numerous Collagen Model Peptides (CMPs) have been engineered using proline derivatives substituted at their C(3) and/or C(4) position in order to stabilize or to functionalize collagen triple helix mimics. However, no example has been reported so far with C(5) substitutions. Here, we introduce a fluorinated CMP incorporating trifluoromethyl groups at the C(5) position of pseudoproline residues. In tripeptide models, our NMR and Molecular Dynamics (MD) studies have shown that, when properly arranged, these residues meet the structural requirements for triple helix assembly. A host-guest CMP could be synthesized and its NMR analysis in solution confirmed the presence of structured homotrimers that we interpret as triple helices. MD calculations showed that the triple helix model remained stable throughout the simulation, with all six trifluoromethyl groups pointing outwards from the triple helix. Pseudoprolines substituted at the C(5) positions appeared as valuable tools for the design of new fluorinated collagen mimicking peptides.

Keywords

peptide
collagen model peptide
fluorine
NMR
Molecular dynamics

Supplementary materials

Title
Description
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Title
Supplementary Information: Inviting trifluoromethylated pseudoprolines into collagen model peptides.
Description
Table of content: 1. Material and methods, general considerations 2. Detailed synthetic procedures 3. NMR spectra 4. NMR Analysis 5. MD simulations
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