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N-Formyl-Met-Leu-Phe

Name: N-Formyl-Met-Leu-Phe
Brand: SIGMA

≥99.0% (TLC), BioXtra

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₂₁H₃₁N₃O₅S

CAS Number:

59880-97-6

Molecular Weight:

437.55

Beilstein:

2315783

MDL number:

MFCD00036780

UNSPSC Code:

12352209

PubChem Substance ID:

57651094

NACRES:

NA.26

product name

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

product line

BioXtra

Quality Level

100

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)

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Related Categories

Amino Acids

High-Purity Biochemicals and Reagents

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.

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’.

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The synthetic chemoattractant Trp-Lys-Tyr-Met-Val-DMet activates neutrophils preferentially through the lipoxin A(4) receptor.

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

The TLR7/8 agonist CL097 primes N-formyl-methionyl-leucyl-phenylalanine-stimulated NADPH oxidase activation in human neutrophils: critical role of p47phox phosphorylation and the proline isomerase Pin1.

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

Off-pump coronary artery bypass surgery induces prolonged alterations to host neutrophil physiology.

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

Inhibition of mammalian target of rapamycin aggravates the respiratory burst defect of neutrophils from decompensated patients with cirrhosis.

Loïc Rolas et al.

Hepatology (Baltimore, Md.), 57(3), 1163-1171 (2012-10-20)

Cirrhosis is commonly accompanied by impaired defense functions of polymorphonuclear leucocytes (PMNs), increased patient susceptibility to infections, and hepatocellular carcinoma (HCC). PMN antimicrobial activity is dependent on a massive production of reactive oxygen species (ROS) by nicotinamide adenine dinucleotide phosphate

Neutrophil infiltration during inflammation is regulated by PILRα via modulation of integrin activation.

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

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