Diphenylacetylene-linked peptide strands induce bidirectional β-sheet formation

Hannah Lingard, Jeongmin T. Han, Amber L. Thompson, Ivanhoe K H Leung, Richard T W Scott, Sam Thompson, Andrew Hamilton

Research output: Contribution to journalArticle

Abstract

In the search for synthetic mimics of protein secondary structures relevant to the mediation of protein-protein interactions, we have synthesized a series of tetrasubstituted diphenylacetylenes that display β-sheet structures in two directions. Extensive X-ray crystallographic and NMR solution phase studies are consistent with these proteomimetics adopting sheet structures, displaying both hydrophobic and hydrophilic amino acid side chains. The importance of β-sheet structures at the interface of protein-protein interactions has prompted the development of a range of synthetic strategies to template and stabilize this secondary structural motif. A tetrasubstituted diphenylacetylene is examined as a central nucleating point for the projection of extended sheet structures in two directions.

Original languageEnglish (US)
Pages (from-to)3650-3653
Number of pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number14
DOIs
StatePublished - Apr 1 2014

Fingerprint

Peptides
Proteins
Amino acids
Nuclear magnetic resonance
biphenylacetylene
Amino Acids
X rays
Direction compound

Keywords

  • beta-sheets
  • peptidomimetics
  • protein surfaces
  • protein-protein interactions
  • secondary structures

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Lingard, H., Han, J. T., Thompson, A. L., Leung, I. K. H., Scott, R. T. W., Thompson, S., & Hamilton, A. (2014). Diphenylacetylene-linked peptide strands induce bidirectional β-sheet formation. Angewandte Chemie - International Edition, 53(14), 3650-3653. https://doi.org/10.1002/anie.201309353

Diphenylacetylene-linked peptide strands induce bidirectional β-sheet formation. / Lingard, Hannah; Han, Jeongmin T.; Thompson, Amber L.; Leung, Ivanhoe K H; Scott, Richard T W; Thompson, Sam; Hamilton, Andrew.

In: Angewandte Chemie - International Edition, Vol. 53, No. 14, 01.04.2014, p. 3650-3653.

Research output: Contribution to journalArticle

Lingard, Hannah ; Han, Jeongmin T. ; Thompson, Amber L. ; Leung, Ivanhoe K H ; Scott, Richard T W ; Thompson, Sam ; Hamilton, Andrew. / Diphenylacetylene-linked peptide strands induce bidirectional β-sheet formation. In: Angewandte Chemie - International Edition. 2014 ; Vol. 53, No. 14. pp. 3650-3653.
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