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For‐Met‐Lys‐Phe‐ For‐Met‐Lys‐Phe‐: A new cyclic analogue of the chemotactic formylpeptides
Author(s) -
Torrini I.,
Zecchini G. Pagani,
Paradisi M. Paglialunga,
Lucente G.,
Gavuzzo E.,
Mazza F.,
Pochetti G.,
Traniello S.,
Spisani S.
Publication year - 1995
Publication title -
biopolymers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.360350402
Subject(s) - chemistry , chemotaxis , stereochemistry , moiety , cyclic peptide , ligand (biochemistry) , ring (chemistry) , sequence (biology) , superoxide , receptor , peptide , biochemistry , enzyme , organic chemistry
As a continuation of the studies on chemotactic N ‐formylpeptides, we report here the synthesis and activity of a new cyclic analogue of the prototypical ligand For‐Met‐Leu‐Phe‐OMe. The new compound contains a 20‐membered cyclic moiety made up of a dimeric‐Lys‐Phe‐sequence in which For‐Met is attached to each Lys α‐NH 2 ‐and hence remains outside the ring. The conformation in the crystal of the cyclic precursor of 4 , namely and the activity of the structurally related linear analogue For‐Met‐Lys(Z)‐Phe‐OBzl ( 6 ), have also been examined. The new analogues 4 and 6 are active as chemoattractants, secretagogues and superoxide anion generating agents, when tested on human neutrophils. The structure‐activity relationship is discussed and related to that of a previously studied cyclic model. © 1995 John Wiley & Sons, Inc.