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Merck
CN

47729

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)

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About This Item

Empirical Formula (Hill Notation):
C21H31N3O5S
CAS Number:
59880-97-6
Molecular Weight:
437.55
NACRES:
NA.26
PubChem Substance ID:
57651094
UNSPSC Code:
12352209
MDL number:
MFCD00036780
Beilstein/REAXYS Number:
2315783

Key Documents

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Product Name

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

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

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 key

PRQROPMIIGLWRP-BZSNNMDCSA-N

product line

BioXtra

assay

≥99.0% (TLC)

form

powder

color

white

solubility

DMF: 50 mg/mL, clear, colorless

application(s)

cell analysis

storage temp.

2-8°C

Quality Level

100

Gene Information

human ... FPR1(2357)

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Related Categories

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN0534
BCCK3106
BCCH2160
BCCC3535
BCBT6614

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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
Astrid L Voskamp et al.
The journal of allergy and clinical immunology. In practice, 3(2), 192-199 (2015-02-03)
Allergic bronchopulmonary aspergillosis (ABPA) often presents with persistently uncontrolled asthma despite the use of corticosteroids and antifungal therapy. Omalizumab is a humanized anti-IgE monoclonal antibody currently used to treat severe asthma. The aim was to assess the clinical and immunologic
Alexandra F Santos et al.
The Journal of allergy and clinical immunology, 134(3), 645-652 (2014-07-30)
Most of the peanut-sensitized children do not have clinical peanut allergy. In equivocal cases, oral food challenges (OFCs) are required. However, OFCs are laborious and not without risk; thus, a test that could accurately diagnose peanut allergy and reduce the
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
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