Skip to Content
Merck
All Photos(1)

Key Documents

47729

Sigma-Aldrich

N-Formyl-Met-Leu-Phe

≥99.0% (TLC), BioXtra

Synonym(s):

Chemotactic peptide, N-Formyl-L-methionyl-L-leucyl-L-phenylalanine, fMLF, fMLP (misnomer but widely used)

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C21H31N3O5S
CAS Number:
Molecular Weight:
437.55
Beilstein:
2315783
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.26

product name

N-Formyl-Met-Leu-Phe, BioXtra, ≥99.0% (TLC)

product line

BioXtra

Quality Level

Assay

≥99.0% (TLC)

form

powder

color

white

solubility

DMF: 50 mg/mL, clear, colorless

application(s)

cell analysis

storage temp.

2-8°C

SMILES string

CSCC[C@H](NC=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1ccccc1)C(O)=O

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

Gene Information

human ... FPR1(2357)

Looking for similar products? Visit Product Comparison Guide

Amino Acid Sequence

NFor-Met-Leu-Phe

Application

1. 4th and 5th applications do not have access
2. 3rd application is not relevant

Biochem/physiol Actions

N-Formyl-Met-Leu-Phe is a potent chemotactic peptide and formyl peptide receptor (FPR) agonist that induces a metabolic burst in macrophages accompanied by an increase in respiratory rate, secretion of lysosomal enzymes, and production of superoxide anion.
Potent chemotactic peptide. Induces a metabolic burst in macrophages accompanied by an increase in respiratory rate, secretion of lysosomal enzymes, and production of superoxide anion.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

C Dahlgren et al.
Blood, 95(5), 1810-1818 (2000-02-26)
A D-methionine-containing peptide, Trp-Lys-Tyr-Met-Val-D-Met-NH(2) (WKYMVm), featuring a unique receptor specificity was investigated with respect to its ability to activate neutrophil effector functions. The peptide was found to be more potent than the N-formylated peptide N-formyl-Met-Leu-Phe (fMLF) at inducing neutrophil chemotaxis
J James B Edelman et al.
Shock (Augusta, Ga.), 39(2), 149-154 (2013-01-18)
Persistent alteration to host polymorphonuclear cell (PMN) physiology has been demonstrated after cardiac surgery performed with cardiopulmonary bypass (CPB). However, to date, PMN physiology and function beyond the first 24 h have not been investigated after cardiac surgery performed without
Karama Makni-Maalej et al.
Journal of immunology (Baltimore, Md. : 1950), 189(9), 4657-4665 (2012-09-25)
Superoxide anion production by the neutrophil NADPH oxidase plays a key role in host defense; however, excessive superoxide production is believed to participate to inflammatory reactions. Neutrophils express several TLR that recognize a variety of microbial motifs or agonists. The
Isaac M Chiu et al.
Nature, 501(7465), 52-57 (2013-08-24)
Nociceptor sensory neurons are specialized to detect potentially damaging stimuli, protecting the organism by initiating the sensation of pain and eliciting defensive behaviours. Bacterial infections produce pain by unknown molecular mechanisms, although they are presumed to be secondary to immune
Jing Wang et al.
Nature immunology, 14(1), 34-40 (2012-11-13)
Acute inflammatory responses are important in host defense, whereas dysregulated inflammation results in life-threatening complications. Here we found that paired immunoglobulin-like type 2 receptor alpha (PILRα), an inhibitory receptor containing immunoreceptor tyrosine-based inhibitory motifs (ITIMs), negatively regulated neutrophil infiltration during

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service