SYNTHESIS AND CHEMOTACTIC ACTIVITY OF THE FMLP ANALOG HCO-HMB-LEU-PHE-OME

The new fMLP analog HCO-Hmb-Leu-Phe-OMe (1), containing (S)-2-hydroxy- 4-(methylthio)butyric acid (Hmb) in place of L-methionine at the N-ter minal position, has been synthesized and fully characterized. The pept ide 1 has been designed in order to improve the understanding of the r ole exerted by the formamido group in the binding interaction with the formylpeptide chemotactic receptors. Chemotaxis, superoxide anion pro duction, and lysozyme release have been measured for both 1 and its de formylated analog Hmb-Leu-Phe-OMe 2. Results indicate that a strong hy drogen bond of the OH .... O=C type may complement a weak H-bonding in teraction involving the formylic proton as H-bond donor.