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Synthesis, conformation, and biological activity of two fMLP‐OMe analogues containing the new 2‐[2′‐(methylthio) ethyl] methionine residue
Author(s) -
Torrini I.,
Paradisi M. Paglialunga,
Zecchini G. Pagani,
Lucente G.,
Gavuzzo E.,
Mazza F.,
Pochetti G.,
Traniello S.,
Spisani S.
Publication year - 1997
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/(sici)1097-0282(19971005)42:4<415::aid-bip5>3.0.co;2-t
Subject(s) - chemistry , tripeptide , residue (chemistry) , methionine , stereochemistry , lysozyme , tetrapeptide , biological activity , amino acid , peptide , biochemistry , in vitro
The new C α ‐tetrasubstituted α‐amino acid residue 2‐[2′‐(methylthio) ethyl]methionine (Dmt) has been introduced into the reference chemotactic tripeptide HCO‐Met‐Leu‐Phe‐OMe (fMLP‐OMe) in place of the leucine or methionine, respectively. The biological activity of the new analogues [Dmt 2 ] fMLP‐OMe (2) and [Dmt 1 ] fMLP‐OMe (3) has been determined; whereas 2 is active toward human neutrophils, stimulating directed migration, superoxide anion generation, and lysozyme release, 3 results practically inactive in all tested assays. A conformational analysis on 2 and 3 has been performed in solution by using ir absorption and 1 H‐nmr. The conformation of 2 was also examined in the crystal by x‐ray diffraction methods. Both 2 and 3 adopt fully extended conformation in correspondence with the Dmt residue. Biological and conformational results are discussed and compared with related previously studied models. © 1997 John Wiley & Sons, Inc. Biopoly 42: 415–426, 1997