Hybrid alpha/beta-peptides: for-Met-Leu-Phe-OMe analogues containing geminally disubstituted beta2,2- and beta 3,3-amino acids at the central position.
The two fMLF-OMe analogues For-Met-beta(3)hAc(6)c-Phe-OMe (6) and For-Met-beta(2)hAc(6)c-Phe-OMe (12) and their corresponding N-Boc derivatives 5 and 11 have been synthesized and their biological activity towards human neutrophils evaluated. The N-formyl peptides 6 and 12 exhibit good activity as chemoattractans and 12 is highly active in superoxide anion production. The preferred solution conformation of the two N-formyl derivatives has been discussed.
Dipartimento di Studi Farmaceutici, Università degli Studi di Roma, La Sapienza, Rome, Italy.
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A
Mollica
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Paglialunga Paradisi
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D
Torino
S
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Spisani
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G
Lucente
D000596:Amino Acids / Q000737:chemistry*; D006801:Humans; D008024:Ligands; D015394:Molecular Structure; D009240:N-Formylmethionine Leucyl-Phenylalanine / Q000031:analogs & derivatives / Q000737:chemistry* / Q000494:pharmacology; D009504:Neutrophils / Q000187:drug effects*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D017433:Protein Structure, Secondary; D013329:Structure-Activity Relationship
D000596:Amino Acids; D008024:Ligands; D010455:Peptides; D009240:N-Formylmethionine Leucyl-Phenylalanine