128175-88-2

Upstream product

• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 105990-13-4 t-Boc-Phe-D-Leu-OH 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 5845-53-4 (R)-leucine methyl ester hydrochloride 
• 99597-71-4 methyl-(N-Boc-L-phenylalanine)-D-leucinate 

Relevant academic research and scientific papers

C- and N-terminal residue effect on peptide derivatives' antagonism toward the formyl-peptide receptor

The biological action of several X-Phe-D-Leu-Phe-D-Leu-Z (X = 3′,5′-dimethylphenyl-ureido; Z = Phe, Lys, Glu, Tyr) analogues was analysed on human neutrophils to evaluate their ability to antagonize formyl-peptide receptors. X-Phe-D-Leu-Phe-D-Leu-Phe analogues obtained as C-terminal olo or amido derivatives and T-Phe-D-Leu-Phe-D-Leu-Phe analogues (T = thiazolyl-ureido) were also analysed. The activities of pentapeptide derivatives were compared with those of X-Phe-D-Leu-Phe-D-Leu-Phe chosen as reference antagonist. Our results demonstrate that X-Phe-D-Leu-Phe-D-Leu-Phe-olo, X-Phe-D-Leu-Phe-D-Leu-Glu and X-Phe-D-Leu-Phe-D-Leu-Tyr are more active antagonists than X-Phe-D-Leu-Phe-D-Leu-Phe. The presence of Lys (X-Phe-D-Leu-Phe-D-Leu-Lys) seems, instead, to inhibit the formyl-peptide receptor antagonist properties. The presence of the N-terminal thiazolyl-ureido group seems to considerably contribute to the receptor antagonist properties of T-Phe-D-Leu-Phe-D-Leu-Phe-OH. The introduction of the C-terminal methyl ester (T-Phe-D-Leu-Phe-D-Leu-Phe-OMe) or amido group (X-Phe-D-Leu-Phe-D-Leu-Phe-NH2) appears detrimental for the affinity and formyl-peptide receptor antagonist properties of the Phe-D-Leu-Phe-D-Leu-Phe derivatives. The examined peptides inhibit superoxide anion production and lysozyme release more efficaciously than neutrophil chemotaxis.