Title of article :
The effect of the cyclopropyl group on the conformation of chemotactic formyl tripeptides
Author/Authors :
Headley، نويسنده , , Allan D. and Ganesan، نويسنده , , Rajeswari and Nam، نويسنده , , Jaewook، نويسنده ,
Issue Information :
روزنامه با شماره پیاپی سال 2003
Pages :
10
From page :
99
To page :
108
Abstract :
Certain formyl peptides are powerful chemoattractants towards neutrophils. In this study, several formyl tripeptides were synthesized and used to investigate the effects of different amino acid residues in position 1 on their ability to stimulate neutrophil chemotaxis. Pig neutrophil chemotaxis towards the formyl tripeptide, HCO–Ac3C–Leu–Phe–OMe 1, where Ac3C represents 1-amino-1-cyclopropane carboxylic acid, was observed. Pig neutrophil chemotaxis towards a very similar formyl tripeptide, HCO–Aib–Leu–Phe–OMe 2, where Aib represents α-amino isobutyric acid, was not observed. Compared to the isopropyl group, it was shown that the cyclopropyl group induces a greater percentage of the E conformation about the formamide functionality in these peptides. For 1 and 2, the E isomer distributions in CDCl3 are 36 and 9%, respectively. Since a major difference between these two peptides is the Z/E isomeric distribution, one implication is that the peptide–receptor site interactions involving the E conformer are more effective than those of the Z conformer. No pig neutrophil chemotaxis towards the formyl tripeptides, HCO–Ala–Leu–Phe–OMe 3 and HCO–Gly–Leu–Phe–OMe 4 was observed. These formyl tripeptides exhibit a low percentage of the E isomer, similar to that of peptide 2.
Keywords :
chemotaxis , Conformation , Ab initio calculations , NMR spectroscopy , Formyl peptides , Pig neutrophils
Journal title :
Bioorganic Chemistry: an International Journal
Serial Year :
2003
Journal title :
Bioorganic Chemistry: an International Journal
Record number :
1385702
Link To Document :
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