Cis-trans isomerization of peptoid residues in the collagen triple-helix.
Journal
Nature communications
ISSN: 2041-1723
Titre abrégé: Nat Commun
Pays: England
ID NLM: 101528555
Informations de publication
Date de publication:
21 Nov 2023
21 Nov 2023
Historique:
received:
10
06
2023
accepted:
10
11
2023
medline:
23
11
2023
pubmed:
22
11
2023
entrez:
21
11
2023
Statut:
epublish
Résumé
Cis-peptide bonds are rare in proteins, and building blocks less favorable to the trans-conformer have been considered destabilizing. Although proline tolerates the cis-conformer modestly among all amino acids, for collagen, the most prevalent proline-abundant protein, all peptide bonds must be trans to form its hallmark triple-helix structure. Here, using host-guest collagen mimetic peptides (CMPs), we discover that surprisingly, even the cis-enforcing peptoid residues (N-substituted glycines) form stable triple-helices. Our interrogations establish that these peptoid residues entropically stabilize the triple-helix by pre-organizing individual peptides into a polyproline-II helix. Moreover, noting that the cis-demanding peptoid residues drastically reduce the folding rate, we design a CMP whose triple-helix formation can be controlled by peptoid cis-trans isomerization, enabling direct targeting of fibrotic remodeling in myocardial infarction in vivo. These findings elucidate the principles of peptoid cis-trans isomerization in protein folding and showcase the exploitation of cis-amide-favoring residues in building programmable and functional peptidomimetics.
Identifiants
pubmed: 37989738
doi: 10.1038/s41467-023-43469-8
pii: 10.1038/s41467-023-43469-8
pmc: PMC10663571
doi:
Substances chimiques
Peptoids
0
Peptides
0
Collagen
9007-34-5
Proline
9DLQ4CIU6V
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
7571Subventions
Organisme : National Natural Science Foundation of China (National Science Foundation of China)
ID : 92059104
Organisme : National Natural Science Foundation of China (National Science Foundation of China)
ID : 82071977
Informations de copyright
© 2023. The Author(s).
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