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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
Pricing and availability is not currently available.

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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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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK3106
BCCH2160
BCCC3535
BCBT6614
BCBQ2757V

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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
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
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
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
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
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Questions

1–3 of 3 Questions  

  1. How long can this product be stored at -20 when reconstituted in DMSO?

    1 answer

    1. The stability of this product in solution is not determined. However, similar product F3506 states that solutions of N-Formyl-Met-Leu-Phe can be stored, in aliquots, at -20°C for at least six months.

      Helpful?

  2. What is the solubility of the product  47729, N-Formyl-Met-Leu-Phe?

    1 answer

    1. Product is soluble in water (partly), methanol, DMSO (4 mg/ml), ethanol (2 mg/ml), and DMF (Dimethylformamide) (50 mg/ml).

      Helpful?

  3. Can this product be dissolved in DMSO?

    1 answer

    1. Yes, this product can be solubilized in DMSO. The exact concentration at which it may be solubilized is not determined. However, several sources state that it is soluble in DMSO at 30 mg/mL.

      Helpful?

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