Synthesis, biological activity and conformational studies of geometrically restricted tripeptide analogues of the chemoattractant HCO-Met-Leu-Phe-OMe.
The formyl tripeptides containing 2-azetidinecarboxylic acid 2, 2-piperidinecarboxylic acid 3 and norvaline 4 in position 2 were synthesized and their biological activity was evaluated. The conformation of peptides was studied by CD and FT-IR techniques. While 2 and 3 do not show either chemotactic activity or superoxide production, 4 retains both activities.
Boggian
M
M
Dipartimento di Scienze Farmaceutiche, Università di Ferrara.
Vertuani
G
G
Cavicchioni
G
G
Pecoraro
R
R
Scatturin
A
A
Spisani
S
S
D002465:Cell Movement; D002630:Chemotactic Factors / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D009240:N-Formylmethionine Leucyl-Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D009504:Neutrophils / Q000187:drug effects* / Q000378:metabolism / Q000502:physiology; D009842:Oligopeptides / Q000737:chemistry* / Q000494:pharmacology; D011487:Protein Conformation; D012996:Solutions; D013481:Superoxides / Q000378:metabolism
D002630:Chemotactic Factors; D009842:Oligopeptides; D012996:Solutions; D013481:Superoxides; D009240:N-Formylmethionine Leucyl-Phenylalanine; C042932:formylmethionyl-leucyl-phenylalanine methyl ester