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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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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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