Why Proline? Influence of Ring-Size on the Collagen Triple Helix

The effect of four- and six-membered ring-size analogs (azetidine- and piperidine-2-carboxylic acid, H-Aze-OH and H-Pip-OH) of proline on the stability of the collagen triple helix was examined. Computational and nuclear magnetic resonance spectroscopic studies with model compounds and thermal denat...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2020-01, Vol.22 (2), p.348-351
Main Authors: Egli, Jasmine, Schnitzer, Tobias, Dietschreit, Johannes C. B, Ochsenfeld, Christian, Wennemers, Helma
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The effect of four- and six-membered ring-size analogs (azetidine- and piperidine-2-carboxylic acid, H-Aze-OH and H-Pip-OH) of proline on the stability of the collagen triple helix was examined. Computational and nuclear magnetic resonance spectroscopic studies with model compounds and thermal denaturation experiments with collagen peptides showed that the ring-size analogs destabilize the triple helix to a similar extent by either mismatching backbone dihedral angles ϕ and ψ (Pip) or by an unfavorable trans/cis amide bond ratio (Aze).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03528