Synthesis, conformation, and activity of HCO-Met-delta Z Leu-Phe-OMe, an active analogue of chemotactic N-formyltripeptides

Biopolymers
G Pagani ZecchiniA Di Nola

Abstract

In order to induce a beta-turn conformation into the chemotactic linear tripeptide N-formyl-L-methionyl-L-leucyl-L-phenylalanine (fMLP), the new analogue N-formyl-L-methionyl-delta Z leucyl-L-phenylalanine methyl ester [delta Z Leu]2fMLP-OMe (1) has been synthesized. The conformational and biochemical consequences of this chemical modification have been determined. Analogue 1 has been synthesized by using N-carboxy-(Z)-alpha,beta-didehydroleucine anhydride as key compound to introduce the unsaturated residue at the central position of the tripeptide 1. The x-ray analysis shows that 1 adopts in the crystal a type II beta-turn conformation in which the new residue occupies the (i + 2) position, and an intramolecular H bond is formed between the formylic oxygen and the Phe NH. 1H-nmr analysis based on nuclear Overhauser effect measurements suggests that the same folded conformation is preferred in CDCl3 solution; this finding is also supported by molecular dynamics simulation. The biological activity of 1 has been determined on human neutrophils (polymorphonuclear leukocytes) and compared to that shown by fMLP-OMe. Chemotactic activity, granule enzyme release, and superoxide anion production have been determined. Analogue 1 is pra...Continue Reading

References

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Citations

Jan 1, 1996·Biopolymers·O PieroniV S Chauhan
Jan 1, 1996·Journal of Peptide Science : an Official Publication of the European Peptide Society·A TuziO Pieroni
Aug 22, 2006·Bioorganic Chemistry·Giorgio CavicchioniSusanna Spisani
Mar 7, 2006·European Journal of Pharmacology·Rita SelvaticiSusanna Spisani
Nov 16, 2019·The Journal of Organic Chemistry·Daniel JoaquinSteven L Castle
Jan 1, 1996·Progress in Biophysics and Molecular Biology·T P Singh, P Kaur

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