ISSN:
0006-3525
Keywords:
chemotaxis
;
conformation
;
crystal structure
;
Cα-tetrasubstituted amino acids
;
formylpeptides
;
2-[2′-(methylthio)ethyl]methionine
;
Chemistry
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The new Cα-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 [Dmt2] fMLP-OMe (2) and [Dmt1] 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 1H-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
Additional Material:
6 Ill.
Type of Medium:
Electronic Resource
