"@-Tides": The 1,2-dihydro-3(6h)-pyridinone unit as a β-strand mimic

S. T. Phillips, M. Rezac, U. Abel, M. Kossenjans, P. A. Bartlett

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63 Scopus citations

Abstract

The cyclic amino acid surrogate 1 was designed to mimic the extended conformation of a peptide unit and to provide hydrogen bond donor and acceptor functions conducive to β-sheet formation. A convenient synthesis of this unit and solution and solid-phase methods for its incorporation into an oligomer alternating with peptide units have been devised. The resulting "@-tides", as these oligomers have been designated, show a high propensity for self-association in comparison to oligopeptides; insights into the structure and dynamical properties of their antiparallel dimers have been obtained by NMR.

Original languageEnglish (US)
Pages (from-to)58-66
Number of pages9
JournalJournal of the American Chemical Society
Volume124
Issue number1
DOIs
Publication statusPublished - Jan 9 2002

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Phillips, S. T., Rezac, M., Abel, U., Kossenjans, M., & Bartlett, P. A. (2002). "@-Tides": The 1,2-dihydro-3(6h)-pyridinone unit as a β-strand mimic. Journal of the American Chemical Society, 124(1), 58-66. https://doi.org/10.1021/ja0168460