"@-Tides": the 1,2-dihydro-3(6H)-pyridinone unit as a beta-strand mimic. |
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| Authors: | Scott T Phillips Miroslav Rezac Ulrich Abel Michael Kossenjans Paul A Bartlett |
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| Institution: | Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720-1460, USA. |
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| 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 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. |
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