“@-Tides”:  The 1,2-Dihydro-3(6H)-pyridinone Unit as a β-Strand Mimic [J. Am. Chem. Soc. 2002, 124, 58−66].

Beta-Strand Mimetics

“…A further variation has included the use of the 1,2dihydro-3(6H)-pyridinone unit (or azacyclohexenone unit and termed Ach or @) as a β-strand mimetic. [260][261][262] Alternating oligomers that contain the cyclic amino acid replacement were termed @-tides. NMR studies of the penta-@-tide 96 261 supported a β-sheet model of dimerization that indicated the ability of 96 to mimic a β-strand.…”

Update 1 of: Beta-Strand Mimetics

“…314 A mimetic was sought to replace the P3-P2 Val-Ala dipeptide segment of the native substrate but maintain the P3 carbonyl and NH, to ensure integrity of this -sheet hydrogen-bonding motif. [330][331][332] Alternating oligomers that contain the cyclic amino acid replacement were termed @-tides. Use of the pyridone ring as a scaffold has led to the recent development of compounds targeting uropathic E. coli, prolyl oligopeptidase, thrombin, and falcipain2/3.…”

“…[326][327][328][329] A further variation has included the use of the 1,2-dihydro-3(6H)-pyridinone unit (or azacyclohexenone unit and termed Ach or @) as a β-strand mimetic. [330][331][332] Alternating oligomers that contain the cyclic amino acid replacement were termed @-tides. NMR studies of the penta-@-tide 131 331 supported a β-sheet model of dimerization that indicated the ability of 131 to mimic a β-strand.…”

Bispidine as a β-strand nucleator: from a β-arch to self-assembled cages and vesicles

“…Nucleation of secondary structure is achieved by the introduction of a rigid unit that favors the initial hydrogen-bonding pattern of α-helix or β-strand as per the nucleating preference of the scaffold. [6][7][8][9][16][17][18] However, there are limited examples of isolated β-strands. Most of the designed scaffolds act by facilitating initial hydrogen bonding to form a sheet that further propagates the β-sheet structure.…”