Synthetic homo-oligomethionine chemoattractants. Conformation-activity study.
Using solution methods, we have synthesized several series of L-methionine homo-oligopeptides from the dipeptide to the hexapeptide with either a free alpha-carboxyl function or different C-blocking groups (methoxy, benzyloxy, benzylamino) and with N-blocking groups of either the amide type (formyl, pivaloyl) or the urethane type (tert.-butyloxycarbonyl). Compounds were compared to determine the combined effect of main-chain length and presence and nature of N- and C-blocking groups on conformation-activity relationship. Each peptide was tested for its ability to induce rabbit peritoneal polymorphonuclear leukocytes in the presence of cytochalasin B to secrete granule enzymes. In parallel, a conformational analysis was carried out in the solid state and in solution, using infrared absorption and circular dichroism. The biological and conformational data are discussed in relation to a recently proposed model of the chemotactic peptide receptor of rabbit neutrophils.
D000818:Animals; D002630:Chemotactic Factors / Q000138:chemical synthesis* / Q000494:pharmacology; D002634:Chemotaxis, Leukocyte / Q000187:drug effects*; D002942:Circular Dichroism; D066298:In Vitro Techniques; D008715:Methionine; D009504:Neutrophils / Q000187:drug effects / Q000201:enzymology; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000494:pharmacology; D011487:Protein Conformation; D011817:Rabbits; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
D002630:Chemotactic Factors; D009842:Oligopeptides; D008715:Methionine