Thioamides in the collagen triple helix

Chem Commun (Camb). 2015 Jun 14;51(47):9624-7. doi: 10.1039/c5cc02685g.


To probe noncovalent interactions within the collagen triple helix, backbone amides were replaced with a thioamide isostere. This subtle substitution is the first in the collagen backbone that does not compromise thermostability. A triple helix with a thioamide as a hydrogen bond donor was found to be more stable than triple helices assembled from isomeric thiopeptides.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Circular Dichroism
  • Collagen / chemistry*
  • Entropy
  • Hydrogen Bonding
  • Models, Molecular
  • Protein Structure, Secondary
  • Thioamides / chemistry*


  • Thioamides
  • Collagen