Modified chemotactic peptides: synthesis and activity of an azaTic-containing fMLP-OMe analogue.
The synthesis and the biological activity of a pseudopeptide analogue of the chemotactic N-formyltripeptide fMLP-OMe, containing the azaTic (3,4-dihydro-2(1H)-phthalazinecarboxylic acid) residue replacing the native phenylalanine, is described. Whereas pseudopeptides containing linear alpha-azaamino acids are currently studied, data on the new group of analogues containing cyclic alpha-aza residues capable of limiting the rotameric distribution of the side chains (topological control) are just emerging in the literature. At our best knowledge, the here described [azaTic3]fMLP-OMe represents the first example of the introduction of this new type of alpha-aza residue into a natural bioactive peptide.
Pagani Zecchini
G
G
Dipartimento di Studi Farmaceutici, Università La Sapienza, Roma, Italy.
Torrini
I
I
Paglialunga Paradisi
M
M
Lucente
G
G
Mastropietro
G
G
Spisani
S
S
D002264:Carboxylic Acids / Q000737:chemistry*; D002634:Chemotaxis, Leukocyte; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009240:N-Formylmethionine Leucyl-Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D010793:Phthalazines / Q000737:chemistry*
C116873:3,4-dihydro-2(H)-phthalazine carboxylic acid; D002264:Carboxylic Acids; D010793:Phthalazines; D009240:N-Formylmethionine Leucyl-Phenylalanine; C042932:formylmethionyl-leucyl-phenylalanine methyl ester