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The nucleation of monomeric parallel beta-sheet-like structures and their self-assembly in aqueous solution

Academic Article
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Overview

authors

  • Chitnumsub, P.
  • Fiori, W. R.
  • Lashuel, H. A.
  • Diaz, H.
  • Kelly, Jeffery

publication date

  • January 1999

journal

  • Bioorganic & Medicinal Chemistry  Journal

abstract

  • The aromatic diacid residue 4,6-dibenzofuranbispropionic acid (1) was designed to nucleate a parallel beta-sheet-like structure in small peptides in aqueous solution via a hydrogen-bonded hydrophobic cluster. Even though a 14-membered ring hydrogen bond necessary for parallel beta-sheet formation is favored in simple amides composed of 1, this hydrogen bonding interaction does not appear to be sufficient to nucleate parallel beta-sheet formation in the absence of hydrophobic clustering between the dibenzofuran portion of 1 and the hydrophobic side chains of the flanking alpha-amino acids. The subsequence --hydrophobic residue-1-hydrophobic residue-- is required for folding in the context of a nucleated two-stranded parallel beta-sheet structure. In all cases where the peptidomimetics can fold into two diastereomeric parallel beta-sheet structures having different hydrogen bonding networks, these conformations appear to exchange rapidly. The majority of the parallel beta-sheet structures evaluated herein undergo linked intramolecular folding and self-assembly, affording a fibrillar beta-sheet quaternary structure. To unlink folding and assembly, asymmetric parallel beta-sheet structures incorporating N-methylated alpha-amino acid residues have been synthesized using a new solid phase approach. Residue 1 facilitates the folding of several peptides described within affording a monomeric parallel beta-sheet-like structure in aqueous solution, as ascertained by a variety of spectroscopic and biophysical methods, increasing our understanding of parallel beta-sheet structure.

subject areas

  • Benzofurans
  • Circular Dichroism
  • Furans
  • Hydrogen Bonding
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Peptides
  • Propionates
  • Protein Structure, Secondary
  • Spectroscopy, Fourier Transform Infrared
  • Ultracentrifugation
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Research

keywords

  • 4,6-dibenzofuranbispropionic acid
  • fibril
  • parallel beta-sheet
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Identity

International Standard Serial Number (ISSN)

  • 0968-0896

Digital Object Identifier (DOI)

  • 10.1016/s0968-0896(98)00222-3

PubMed ID

  • 10199655
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Additional Document Info

start page

  • 39

end page

  • 59

volume

  • 7

issue

  • 1

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