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Heterocyclic peptide backbone modifications in an α-helical coiled coil

Academic Article
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Overview

related to degree

  • Yadav, Maneesh, Ph.D. in Chemistry, Scripps Research 2002 - 2006
  • Horne, William Seth, Ph.D. in Chemistry, Scripps Research 2000 - 2005

authors

  • Horne, William Seth
  • Yadav, Maneesh
  • Stout, C. David
  • Ghadiri, M. Reza

publication date

  • December 2004

journal

  • Journal of the American Chemical Society  Journal

abstract

  • In this paper, we present 1,2,3-triazole epsilon2-amino acids incorporated as a dipeptide surrogate at three positions in the sequence of a known alpha-helical coiled coil. Biophysical characterization indicates that the modified peptides retain much of the helical structure of the parent sequence, and that the thermodynamic stability of the coiled coil depends on the position of the incorporation of the epsilon-residue. Crystal structures obtained for each peptide give insight into the chemical behavior and conformational preferences of the non-natural amino acid and show that the triazole ring can participate in the backbone hydrogen bonding of the alpha-helix as well as template an interhelical crossing between chains in the bundle.

subject areas

  • Amino Acid Sequence
  • Amino Acids
  • Crystallography, X-Ray
  • DNA-Binding Proteins
  • Dipeptides
  • Hydrogen Bonding
  • Leucine
  • Models, Molecular
  • Molecular Sequence Data
  • Protein Kinases
  • Protein Structure, Secondary
  • Saccharomyces cerevisiae Proteins
  • Thiazoles
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Identity

PubMed Central ID

  • PMC1868409

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja0450408

PubMed ID

  • 15563148
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Additional Document Info

start page

  • 15366

end page

  • 15367

volume

  • 126

issue

  • 47

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