"@-Tides": the 1,2-dihydro-3(6H)-pyridinone unit as a beta-strand mimic.
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 beta-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.
Phillips
Scott T
ST
Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720-1460, USA.
Rezac
Miroslav
M
Abel
Ulrich
U
Kossenjans
Michael
M
Bartlett
Paul A
PA
D007700:Kinetics; D018716:Molecular Mimicry; D019906:Nuclear Magnetic Resonance, Biomolecular; D009842:Oligopeptides / Q000737:chemistry*; D017433:Protein Structure, Secondary; D011728:Pyridones / Q000138:chemical synthesis / Q000737:chemistry*; D013696:Temperature
D009842:Oligopeptides; D011728:Pyridones