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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)

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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

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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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’.

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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
Lunhua Liu et al.
Molecular biology of the cell, 23(24), 4751-4765 (2012-10-26)
Integrin activation is required to facilitate multiple adhesion-dependent functions of neutrophils, such as chemotaxis, which is critical for inflammatory responses to injury and pathogens. However, little is known about the mechanisms that mediate integrin activation in neutrophils. We show that
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
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