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W4270

Sigma-Aldrich

WKYMVM trifluoroacetate salt

≥98% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C41H61N9O7S2 · xC2HF3O2
CAS Number:
187986-11-4
Molecular Weight:
856.11 (free base basis)
MDL number:
MFCD19443869
UNSPSC Code:
51111800
PubChem Substance ID:
329830691
NACRES:
NA.32

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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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
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
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

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