Synthesis, conformation, and biological activity of two fMLP-OMe analogues containing the new 2-[2′-(methylthio) ethyl] methionine residue
✍ Scribed by I. Torrini; M. Paglialunga Paradisi; G. Pagani Zecchini; G. Lucente; E. Gavuzzo; F. Mazza; G. Pochetti; S. Traniello; S. Spisani
- Publisher
- Wiley (John Wiley & Sons)
- Year
- 1997
- Tongue
- English
- Weight
- 196 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0006-3525
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✦ Synopsis
The new C a -tetrasubstituted a-amino acid residue 2- [2-(methylthio)ethyl]methionine (Dmt) has been introduced into the reference chemotactic tripeptide HCO-Met-Leu-Phe-OMe ( f MLP-OMe) in place of the leucine or methionine, respectively. The biological activity of the new analogues [Dmt 2 ] f MLP-OMe ( 2) and [Dmt 1 ] f MLP-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.