220563-70-2Relevant academic research and scientific papers
Solid-Phase Synthesis of Peptides Containing Reverse-Turn Mimetic Bicyclic Lactams
Genarri, Cesare,Mielgo, Antonia,Potenza, Donatella,Scolastico, Carlo,Piarulli, Umberto,Manzoni, Leonardo
, p. 379 - 388 (2007/10/03)
The solid-phase synthesis and characterization of a series of peptides (4-15) containing reverse-turn mimetic bicyclic lactams is reported. The bicyclic lactams (1a, 1b) possess high structural similarity to the two central residues of a β-turn. Amino acid conjugates of these bicyclic lactams were synthesized on solid supports following a 9-fluorenylmethoxycarbonyl (FMOC) protection strategy on Wang-Merrifield resin. Coupling between amino acids was accomplished by means of diisopropylcarbodiimide (DIC)/hydroxyazabenzotriazole (HOAt). Coupling between amino acids and the mimics was performed with the potent Carpino's reagent O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU). The final compounds were cleaved from the resin and obtained as N-acetylated methyl esters or benzyl amides.
