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Open Access Publications from the University of California

Synthesis of amino acid-derived cyclic acyl amidines for use in β-strand peptidomimetics

  • Author(s): Hammond, MC
  • Bartlett, PA
  • et al.

(Chemical Equation Presented) The acyl amidine represented by the 4,5-dihydro-2(3H)-pyrazinone ring system 2 is isosteric to the vinylogous amide of the 1,2-dihydro-3(6H)-pyridinone 1, but its assembly from separate amine and amide components enables ready incorporation of an amino acid side chain with correct regio- and stereochemistry. β-Strand peptidomimetics incorporating amino acid analogues based on 2 have recently been shown to be potent, protease-resistant ligands to a PDZ protein-interaction domain. Two routes to the protected dipeptide analogue 3 are described. © 2007 American Chemical Society.

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