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A convenient synthetic procedure for the preparation of seven-membered cyclic α,β-dipeptides is described. Following coupling of N-protected α-amino acids with N-substituted β-amino acid tert-butyl esters, that affords linear α,β-dipeptides, the protecting groups at the terminal functionalities were removed and the open-chain dipeptides were cyclized with phenylphosphonic dichloride, PhP(O)Cl ...
The pyrokinin/pheromone biosynthesis activating neuropeptide (PK/PBAN) family plays a significant role in a multifunctional array of important physiological processes in insects. PK/PBAN analogs incorporating β-amino acids were synthesized and evaluated in a pheromonotropic assay in Heliothis peltigera, a melanotropic assay in Spodoptera littoralis, a pupariation assay in Neobellieria bullata, and...
The multifunctional arthropod ‘insect kinins’ share the evolutionarily conserved C-terminal pentapeptide motif Phe-X 1 -X 2 -Trp-Gly-NH 2 , where X 1 =His, Asn, Ser, or Tyr and X 2 =Ser, Pro, or Ala. Eight different analogs of the insect kinin C-terminal pentapeptide active core in which the critical residues Phe 1 , Pro 3 and Trp 4 are...
β 2 -(3,4-Dihydroxybenzyl)-β-alanine [β 2 -Homo-Dopa, 1] is a novel β-amino acid homologue of Dopa, the most successful therapeutic agent in the treatment of Parkinson's disease. Enantioenriched (R)-1 and (S)-1 were obtained via the diastereoselective alkylation of enantiopure pyrimidinone (R)- and (S)-3, chiral derivatives of β-alanine, with veratryl iodide. The major diastereomeric...
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