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Chemotactic Peptide Analogues. Synthesis and Chemotactic Activity of N‐Formyl‐Met‐Leu‐Phe Analogues Containing (S)‐Phenylalaninol Derivatives

Giampiero Pagani Zecchini, Mario Paglialunga Paradisi, Ines Torrini, Susanna Spisani

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Abstract

The synthesis and the biological activity towards human neutrophils of some N-formyl-Met-Leu-Phe-OMe analogues containing (S)-phenylalaninol (Pheol) or its derivatives in place of the native phenylalanine are reported. While the analogue containing Pheol (4) was found to be devoid of significant biological activity, its esters 3 and 5, although inactive as chemoattractants, are able to strongly stimulate superoxide production and are active with a lower efficacy in the lysozyme release.

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The synthesis and the biological activity towards human neutrophils of some N-formyl-Met-Leu-Phe-OMe analogues containing (S)-phenylalaninol (Pheol) or its derivatives in place of the native phenylalanine are reported. While the analogue containing Pheol (4) was found to be devoid of significant biological activity, its esters 3 and 5, although inactive as chemoattractants, are able to strongly stimulate superoxide production and are active with a lower efficacy in the lysozyme release.

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Available abstract

The synthesis and the biological activity towards human neutrophils of some N-formyl-Met-Leu-Phe-OMe analogues containing (S)-phenylalaninol (Pheol) or its derivatives in place of the native phenylalanine are reported. While the analogue containing Pheol (4) was found to be devoid of significant biological activity, its esters 3 and 5, although inactive as chemoattractants, are able to strongly stimulate superoxide production and are active with a lower efficacy in the lysozyme release.

Key concepts: Chemotaxis, Chemistry, Biological activity, Superoxide, Chemical synthesis, Peptide, Formyl peptide receptor, Lysozyme

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Chemotactic Peptide Analogues. Synthesis and Chemotactic Activity of N‐Formyl‐Met‐Leu‐Phe Analogues Containing (S)‐Phenylalaninol Derivatives — Research Paper | ScholarLens