Peptide bond isosteres: ester or (E)-alkene in the backbone of the collagen triple helix - PubMed (original) (raw)

. 2005 Jun 23;7(13):2619-22.

doi: 10.1021/ol050780m.

Affiliations

• PMID: 15957905
• DOI: 10.1021/ol050780m

Peptide bond isosteres: ester or (E)-alkene in the backbone of the collagen triple helix

Cara L Jenkins et al. Org Lett. 2005.

Abstract

[structure: see text] Collagen is the most abundant protein in animals. Interstrand N-H...O=C hydrogen bonds between backbone amide groups form a ladder in the middle of the collagen triple helix. Isosteric replacement of the hydrogen-bond-donating amide with an ester or (E)-alkene markedly decreases the conformational stability of the triple helix. Thus, this recurring hydrogen bond is critical to the structural integrity of collagen. In this context, an ester isostere confers more stability than does an (E)-alkene.

PubMed Disclaimer

Similar articles

• The effect of a trans-locked Gly-Pro alkene isostere on collagen triple helix stability.
  Dai N, Wang XJ, Etzkorn FA. Dai N, et al. J Am Chem Soc. 2008 Apr 23;130(16):5396-7. doi: 10.1021/ja711021m. Epub 2008 Mar 26. J Am Chem Soc. 2008. PMID: 18366169
• Macrocyclic scaffold for the collagen triple helix.
  Horng JC, Hawk AJ, Zhao Q, Benedict ES, Burke SD, Raines RT. Horng JC, et al. Org Lett. 2006 Oct 12;8(21):4735-8. doi: 10.1021/ol061771w. Org Lett. 2006. PMID: 17020290
• Cis-trans proline isomerization effects on collagen triple-helix stability are limited.
  Dai N, Etzkorn FA. Dai N, et al. J Am Chem Soc. 2009 Sep 30;131(38):13728-32. doi: 10.1021/ja904177k. J Am Chem Soc. 2009. PMID: 19725497
• Triple-helical peptides: an approach to collagen conformation, stability, and self-association.
  Brodsky B, Thiagarajan G, Madhan B, Kar K. Brodsky B, et al. Biopolymers. 2008 May;89(5):345-53. doi: 10.1002/bip.20958. Biopolymers. 2008. PMID: 18275087 Review.
• Collagen structure: the Madras triple helix and the current scenario.
  Bhattacharjee A, Bansal M. Bhattacharjee A, et al. IUBMB Life. 2005 Mar;57(3):161-72. doi: 10.1080/15216540500090710. IUBMB Life. 2005. PMID: 16036578 Review.

Cited by

• The Chemistry and Biology of Collagen Hybridization.
  Li X, Zhang Q, Yu SM, Li Y. Li X, et al. J Am Chem Soc. 2023 May 24;145(20):10901-10916. doi: 10.1021/jacs.3c00713. Epub 2023 May 9. J Am Chem Soc. 2023. PMID: 37158802 Free PMC article. Review.
• Terminal repeats impact collagen triple-helix stability through hydrogen bonding.
  Qi Y, Zhou D, Kessler JL, Qiu R, Yu SM, Li G, Qin Z, Li Y. Qi Y, et al. Chem Sci. 2022 Oct 20;13(42):12567-12576. doi: 10.1039/d2sc03666e. eCollection 2022 Nov 2. Chem Sci. 2022. PMID: 36382282 Free PMC article.
• Disrupting Effects of Osteogenesis Imperfecta Mutations Could Be Predicted by Local Hydrogen Bonding Energy.
  Qiang S, Lu C, Xu F. Qiang S, et al. Biomolecules. 2022 Aug 11;12(8):1104. doi: 10.3390/biom12081104. Biomolecules. 2022. PMID: 36008998 Free PMC article.
• Bifunctional Peptide that Anneals to Damaged Collagen and Clusters TGF-β Receptors Enhances Wound Healing.
  Chattopadhyay S, Teixeira LBC, Kiessling LL, McAnulty JF, Raines RT. Chattopadhyay S, et al. ACS Chem Biol. 2022 Feb 18;17(2):314-321. doi: 10.1021/acschembio.1c00745. Epub 2022 Jan 27. ACS Chem Biol. 2022. PMID: 35084170 Free PMC article.
• A substrate protection approach to applying the calcium ion for improving the proteolysis resistance of the collagen.
  Gao M, Tian Y, Zhang X, Zhang C, Peng B. Gao M, et al. Appl Microbiol Biotechnol. 2021 Dec;105(24):9191-9209. doi: 10.1007/s00253-021-11704-1. Epub 2021 Nov 29. Appl Microbiol Biotechnol. 2021. PMID: 34841465

Publication types

MeSH terms

Substances

LinkOut - more resources

• Full Text Sources

  • American Chemical Society

• Other Literature Sources

  • The Lens - Patent Citations