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47729

Sigma-Aldrich

N-Formyl-Met-Leu-Phe

≥99.0% (TLC), BioXtra

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C21H31N3O5S
Numéro CAS:
59880-97-6
Poids moléculaire :
437.55
Numéro Beilstein :
2315783
Numéro MDL:
MFCD00036780
Code UNSPSC :
12352209
ID de substance PubChem :
57651094
Nomenclature NACRES :
NA.26

product name

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

Gamme de produits

BioXtra

Niveau de qualité

100

Pureté

≥99.0% (TLC)

Forme

powder

Couleur

white

Solubilité

DMF: 50 mg/mL, clear, colorless

Application(s)

cell analysis

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

PRQROPMIIGLWRP-BZSNNMDCSA-N

Informations sur le gène

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

Actions biochimiques/physiologiques

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.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

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
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
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