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F0762

Sigma-Aldrich

N-Formyl-Met-Leu-Phe-o-fluorobenzylamide

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About This Item

Empirical Formula (Hill Notation):
C28H37FN4O3S
CAS Number:
112898-02-9
Molecular Weight:
528.68
MDL number:
MFCD00058596
UNSPSC Code:
12352202
PubChem Substance ID:
24894730
NACRES:
NA.26

form

solid

storage temp.

−20°C

SMILES string

CSCCC(NC=O)C(=O)NC(CC(C)C)C(=O)NC(Cc1ccccc1)C(=O)NCc2ccccc2F

InChI

1S/C28H37FN4O4S/c1-19(2)15-24(32-27(36)23(31-18-34)13-14-38-3)28(37)33-25(16-20-9-5-4-6-10-20)26(35)30-17-21-11-7-8-12-22(21)29/h4-12,18-19,23-25H,13-17H2,1-3H3,(H,30,35)(H,31,34)(H,32,36)(H,33,37)

InChI key

LTOZIPKEOGLEJO-UHFFFAOYSA-N

Amino Acid Sequence

NFor-Met-Leu-Phe-O-FBA

Biochem/physiol Actions

N-Formyl-Met-Leu-Phe-o-fluorobenzylamide is a C-terminal blocked derivative of the chemotatic/chemoattractant tripeptide fMLF. N-Formyl-Met-Leu-Phe-o-fluorobenzylamide may be used to probe human formyl peptide receptors and fMLF functions.

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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Fujie Tanaka et al.
Bioorganic & medicinal chemistry letters, 17(7), 1943-1945 (2007-02-13)
Antibodies that selectively bind to N-formylmethionyl leucyl phenylalanine (fMLF, also known as fMLP) have been generated. These antibodies bound to fMLF with higher affinity than to non-formylated peptide MLF: the differences in the binding energies between fMLF and MLF were
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
Wulin Aerbajinai et al.
Journal of leukocyte biology, 90(3), 529-538 (2011-06-10)
Chemotaxis is fundamental to the directional migration of neutrophils toward endogenous and exogenous chemoattractants. Recent studies have demonstrated that ADF/cofilin superfamily members play important roles in reorganizing the actin cytoskeleton by disassembling actin filaments. GMFG, a novel ADF/cofilin superfamily protein
D C Feller et al.
International journal of peptide and protein research, 34(3), 229-234 (1989-09-01)
Conformational energy analyses were carried out on the chemotactic tripeptide fMLF (CHO-Met-Leu-Phe) and three analogs fALF (CHO-Ala-Leu-Phe). fMF (CHO-Met-Phe), and MLF (H-Met-Leu-Phe). A near-folded or puckered conformation predominates in all four peptides. The calculated average end-to-end distance R of each
Hisakazu Fujita et al.
Archives of biochemistry and biophysics, 516(2), 121-127 (2011-10-19)
Calpain inhibitors, including peptide aldehydes (N-acetyl-Leu-Leu-Nle-CHO and N-acetyl-Leu-Leu-Met-CHO) and α-mercapto-acrylic acid derivatives (PD150606 and PD151746), have been shown to stimulate phagocyte functions via activation of human formyl peptide receptor (hFPR) and/or hFPR-like 1 (hFPRL1). Using the homology modeling of the

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