N-Formyl-Met-Leu-Phe

N-Formyl-Met-Leu-Phe (fMLP; N-Formyl-MLF) is a chemotactic peptide and a specific ligand of N-formyl peptide receptor (FPR). N-Formyl-Met-Leu-Ph is reported to inhibit TNF-alpha secretion.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
N-Formyl-Met-Leu-Phe(CAS 59880-97-6)

CAT No: R1553

CAS No:59880-97-6

Synonyms/Alias:N-Formyl-Met-Leu-Phe;59880-97-6;FMLP;Chemotactic peptide;fMLF;F-Met-leu-phe;N-Formyl-methionyl-leucyl-phenylalanine;fMetLeuPhe;fMet-Leu-Phe;N-Formyl-L-methionyl-L-leucyl-L-phenylalanine;formyl-Met-Leu-Phe;N-FORMYLMETHIONINE LEUCYL-PHENYLALANINE;(S)-2-((S)-2-((S)-2-Formamido-4-(methylthio)butanamido)-4-methylpentanamido)-3-phenylpropanoic acid;MFCD00036780;CHEMBL267179;CHEBI:53490;(2S)-2-[[(2S)-2-[[(2S)-2-formamido-4-methylsulfanylbutanoyl]amino]-4-methylpentanoyl]amino]-3-phenylpropanoic acid;N-Formyl-MLF;fMLP;N-Formyl-MLF;SMR000857394;LO6AVJ8RCE;Formyl-Met-Leu-Phe-OH;fMLP (misnomer but widely used);NSC-350593;L-Phenylalanine, N-formyl-L-methionyl-L-leucyl-;(2S)-2-(((2S)-2-(((2S)-2-FORMAMIDO-4-METHYLSULFANYLBUTANOYL)AMINO)-4-METHYLPENTANOYL)AMINO)-3-PHENYLPROPANOIC ACID;Formyl met leu phe;Chemotactic peptide?;SCHEMBL39529;MLS001361389;MLS002207097;GTPL1022;DTXSID9041077;GLXC-10556;GLXC-26059;HMS2235B23;HY-P0224;formyl-methionyl-leucyl-phenylalanine;BDBM50050937;F-MET-LEU-PHE L-PHENYLALANINE;AKOS024456858;CS-6489;n-formylmethionine-leucine-phenylalanine;AS-57764;N-Formyl-Met-Leu-Phe, >=97% (HPLC);F1158;D90695;N-(N-(N-FORMYL-L-METHIONYL)-L-LEUCYL);Formyl-Met-Leu-Phe-OH - CAS 59880-97-6;Chemotactic Peptide (For-L-Met-L-Leu-L-Phe-OH);N-Formyl-Met-Leu-Phe, BioXtra, >=99.0% (TLC);Q5090627;(2S)-2-[(2S)-2-[(2S)-2-formamido-4-(methylsulfanyl)butanamido]-4-methylpentanamido]-3-phenylpropanoic acid;(S)-2-((S)-2-((S)-2-Formamido-4-(methylthio)butanamido)-4-methylpentanamido)-3-phenylpropanoicacid;(S)-2-[(S)-2-((S)-2-Formylamino-4-methylsulfanyl-butyrylamino)-4-methyl-pentanoylamino]-3-phenyl-propionic acid;

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cGMP Peptide
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M.F/Formula
C21H31N3O5S
M.W/Mr.
437.6
Sequence
One Letter Code:MLF
Three Letter Code:For-Met-Leu-Phe-OH
Purity
≥98%

N-Formyl-Met-Leu-Phe, also known as fMLF or formyl-methionyl-leucyl-phenylalanine, is a synthetic tripeptide widely recognized for its role as a potent chemoattractant in immunological and cellular signaling studies. Structurally, it mimics the N-formylated oligopeptides produced by bacteria, thereby serving as a prototypical ligand for formyl peptide receptors (FPRs) on mammalian phagocytic cells. Its ability to trigger specific cellular responses has made it an indispensable tool in the investigation of innate immune mechanisms, cell migration, and receptor-mediated signal transduction pathways.

Chemotaxis research: fMLF is extensively utilized in studies of leukocyte chemotaxis, where it acts as a model agonist for human and animal neutrophil migration assays. By binding to FPR1 on the surface of neutrophils and other immune cells, it initiates signaling cascades that result in directed cell movement. Researchers employ this peptide to dissect the molecular mechanisms underlying immune cell navigation toward sites of infection or inflammation, providing insight into host-pathogen interactions and inflammatory processes.

Signal transduction analysis: The tripeptide is a cornerstone in elucidating G protein-coupled receptor (GPCR) signaling, particularly those involving the formyl peptide receptor family. Upon binding to its receptor, fMLF activates downstream pathways such as phospholipase C, calcium mobilization, and MAP kinase signaling. These properties make it valuable for studies seeking to unravel the complexities of GPCR-mediated cellular responses, receptor desensitization, and cross-talk between signaling networks in immune cells.

Oxidative burst assays: In functional studies of phagocyte activation, N-Formyl-Met-Leu-Phe is routinely employed to stimulate the respiratory burst, a rapid production of reactive oxygen species (ROS) essential for microbial killing. Its application enables quantitative assessment of ROS generation in neutrophils and macrophages, serving as a benchmark for evaluating the impact of genetic modifications, pharmacological inhibitors, or disease states on the oxidative capabilities of innate immune cells.

Receptor pharmacology: The peptide serves as a reference ligand in pharmacological profiling of formyl peptide receptors and their subtypes. It is used to characterize receptor binding affinities, agonist potencies, and antagonist selectivity in both recombinant expression systems and native cell models. Such studies are critical for the development and validation of new modulators targeting FPRs, with implications for research into inflammation, immune regulation, and host defense mechanisms.

Cellular signaling modulation: Beyond its role in immune cell activation, fMLF is applied in broader investigations of cellular signaling modulation, including studies on cytoskeletal rearrangement, gene expression, and apoptosis induction. Its capacity to induce well-defined and reproducible cellular responses allows researchers to probe the downstream effects of FPR engagement across various cell types, facilitating a deeper understanding of the interconnected pathways that govern cellular physiology in response to external stimuli.

Long-term Storage Conditions
Soluble to 4.38 mg/ml in DMSO
Shipping Condition
Shipped at room temperature
InChI
InChI=1S/C21H31N3O5S/c1-14(2)11-17(23-19(26)16(22-13-25)9-10-30-3)20(27)24-18(21(28)29)12-15-7-5-4-6-8-15/h4-8,13-14,16-18H,9-12H2,1-3H3,(H,22,25)(H,23,26)(H,24,27)(H,28,29)/t16-,17-,18-/m0/s1
InChI Key
PRQROPMIIGLWRP-BZSNNMDCSA-N
Canonical SMILES
O=C(O)[C@@H](N([H])C([C@@H](N(C([C@@H](N(C=O)[H])CCSC)=O)[H])CC(C)C)=O)CC1=CC=CC=C1

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