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Key Documents

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W4270

Sigma-Aldrich

WKYMVM trifluoroacetate salt

≥98% (HPLC)

Sinónimos:

Trp-Lys-Tyr-Met-Val-L-Met NH2 trifluoroacetate salt

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About This Item

Fórmula empírica (notación de Hill):
C41H61N9O7S2 · xC2HF3O2
Número de CAS:
187986-11-4
Peso molecular:
856.11 (free base basis)
MDL number:
MFCD19443869
UNSPSC Code:
51111800
PubChem Substance ID:
329830691
NACRES:
NA.32

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

H2O: >2 mg/mL

shipped in

wet ice

storage temp.

−20°C

SMILES string

OC(=O)C(F)(F)F.CSCC[C@H](NC(=O)[C@@H](NC(=O)[C@H](CCSC)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)Cc2c[nH]c3ccccc23)C(C)C)C(N)=O

InChI

1S/C41H61N9O7S2.C2HF3O2/c1-24(2)35(41(57)46-31(36(44)52)16-19-58-3)50-39(55)33(17-20-59-4)48-40(56)34(21-25-12-14-27(51)15-13-25)49-38(54)32(11-7-8-18-42)47-37(53)29(43)22-26-23-45-30-10-6-5-9-28(26)30;3-2(4,5)1(6)7/h5-6,9-10,12-15,23-24,29,31-35,45,51H,7-8,11,16-22,42-43H2,1-4H3,(H2,44,52)(H,46,57)(H,47,53)(H,48,56)(H,49,54)(H,50,55);(H,6,7)/t29-,31-,32-,33-,34-,35-;/m0./s1

InChI key

MYVYQWVNXDVTBW-CZPFDPCBSA-N

Amino Acid Sequence

Trp-Lys-Tyr-Met-Val-L-Met NH2

Application

WKYMVM trifluoroacetate salt was used as a test compound for investigating the mechanism of regulation of lipoprotein-associated phospholipase A2 (Lp-PLA2).

Biochem/physiol Actions

WKYMVM is a peptide agonist of formyl peptide receptors. WKYMVM binds to and stimulates FPRL family members 1, 2 with EC50 values of 2 and 80 nM, respectively. The peptide is a potent activator of neutrophils.
WKYMVM is an agonist and potent activator of Formyl peptide receptor like-1 (FPRL1). WKYMVM stimulates FPRL1 and hence attenuates the function of the chemokine receptors CCR5 and CXCR4. WKYMVM activates human eosinophils to induce superoxide production through Phosphoinositide 3-Kinase-Mediated ERK1/2 pathway.

Preparation Note

WKYMVM trifluoroacetate salt dissolves in water at a concentration >2 mg/mL to yield a clear solution.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Myeong Heon Shin et al.
International archives of allergy and immunology, 137 Suppl 1, 21-26 (2005-06-11)
Eosinophils play a key role in allergic inflammation and parasitic infections. The synthetic peptide, Trp-Lys-Tyr-Met-Val-D-Met (WKYMVm), has been previously shown to activate eosinophils and thus to enhance respiratory burst through the formyl peptide receptors. This study was undertaken to determine
Bo Li et al.
Atherosclerosis, 228(2), 370-379 (2013-04-30)
Although lipoprotein-associated phospholipase A2 (Lp-PLA2) has been regarded as a biomarker and a causative agent for acute coronary events recently, the mechanism of the regulation of Lp-PLA2 has not been fully elucidated yet. This study was aimed to investigate the
B Q Li et al.
Blood, 97(10), 2941-2947 (2001-05-09)
The G protein-coupled 7 transmembrane (STM) chemoattractant receptors can be inactivated by heterologous desensitization. Earlier work showed that formly peptide receptor-like 1 (FPRL1), an STM receptor with low affinity for the bacterial chemotactic peptide formyl-methionyl-leucyl-phenylalamine (fMLF), is activated by peptide

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