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A3227

Sigma-Aldrich

Ala-Tyr-Pro-Gly-Lys-Phe-NH2 trifluoroacetate salt

≥98% (HPLC), lyophilized powder, PAR4 agonist

Synonym(s):

AYPGKF-NH2, PAR4-AP

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About This Item

Empirical Formula (Hill Notation):
C34H48N8O7 · xC2HF3O2
CAS Number:
1228078-65-6
Molecular Weight:
680.79 (free base basis)
MDL number:
MFCD04974484
UNSPSC Code:
12352202
PubChem Substance ID:
329770819
NACRES:
NA.77
Pricing and availability is not currently available.

Product Name

Ala-Tyr-Pro-Gly-Lys-Phe-NH2 trifluoroacetate salt, ≥98% (HPLC), lyophilized powder

Quality Level

100

assay

≥98% (HPLC)

form

lyophilized powder

color

white

solubility

H2O: >10 mg/mL

storage temp.

−20°C

SMILES string

OC(=O)C(F)(F)F.C[C@H](N)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N2CCCC2C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](Cc3ccccc3)C(N)=O

InChI

1S/C34H48N8O7.C2HF3O2/c1-21(36)31(46)41-27(19-23-12-14-24(43)15-13-23)34(49)42-17-7-11-28(42)33(48)38-20-29(44)39-25(10-5-6-16-35)32(47)40-26(30(37)45)18-22-8-3-2-4-9-22;3-2(4,5)1(6)7/h2-4,8-9,12-15,21,25-28,43H,5-7,10-11,16-20,35-36H2,1H3,(H2,37,45)(H,38,48)(H,39,44)(H,40,47)(H,41,46);(H,6,7)/t21-,25-,26-,27-,28-;/m0./s1

InChI key

BGPJLFVICWHITH-HKJXYENISA-N

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MCE Membrane Filter, 0.8 μm Pore Size MF-Millipore™, filter diam. 47 mm, hydrophilic, white, gridded

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MCE Membrane Filter, 0.8 μm Pore Size MF-Millipore™, filter diam. 25 mm, hydrophilic, white, gridded

AAWG02500

MCE Membrane Filter, 0.8 μm Pore Size

MCE Membrane Filter, 0.8 μm Pore Size MF-Millipore™, filter diam. 13 mm, hydrophilic, white, gridded

AAWG01300

MCE Membrane Filter, 0.8 μm Pore Size

MCE Membrane Filter, 0.8 μm Pore Size MF-Millipore™, filter diam. 13 mm, hydrophilic, black, gridded

AABG01300

MCE Membrane Filter, 0.8 μm Pore Size

pore size

0.8 μm pore size, 82 % porosity

pore size

0.8 μm pore size, 82 % porosity

pore size

0.8 μm pore size, 82 % porosity

pore size

0.8 μm pore size, 82 % porosity

material

gridded , white filter, mixed cellulose esters (MCE) membrane

material

gridded , mixed cellulose esters (MCE) membrane, white filter

material

gridded , mixed cellulose esters (MCE) membrane, white filter

material

black filter, gridded , mixed cellulose esters (MCE) membrane

manufacturer/tradename

MF-Millipore™

manufacturer/tradename

MF-Millipore™

manufacturer/tradename

MF-Millipore™

manufacturer/tradename

MF-Millipore™

parameter

16 L/min-cm2 air flow rate, 75 °C max. temp., 190 mL/min-cm2 water flow rate

parameter

16 L/min-cm2 air flow rate, 190 mL/min-cm2 water flow rate, 75 °C max. temp.

parameter

16 L/min-cm2 air flow rate, 190 mL/min-cm2 water flow rate, 75 °C max. temp.

parameter

16 L/min-cm2 air flow rate, 190 mL/min-cm2 water flow rate, 75 °C max. temp.

sterility

non-sterile

sterility

non-sterile

sterility

-

sterility

non-sterile

feature

hydrophilic

feature

hydrophilic

feature

hydrophilic

feature

hydrophilic

Amino Acid Sequence

Ala-Tyr-Pro-Gly-Lys-Phe-NH2

General description

Ala-Tyr-Pro-Gly-Lys-Phe-NH2 (AYPGKF- NH2) is a selective, specific proteinase-activated receptor 4 (PAR4) agonist peptide. PAR4 is a G-protein-coupled receptor that is expressed on the surface of human platelets and is involved in the thrombin signaling pathway. Cleavage of PAR4 by the protease thrombin stimulates the receptor and results in signaling of platelet aggregation.

Application

4-Androsten-11β-ol-3,17-dione has been used in platelet aggregation.[1]
AYPGKF- NH2 may be used for probing PAR4 signaling in culture systems and in platelets.

Biochem/physiol Actions

AYPGK is a ligand for the PAR4 receptor; binding results in activation of PAR4. AYPGK stimulates platelet aggregation in vitro (EC50 =15 μM) via PAR4. In human platelets treated with the PAR4 agonist, AYPGKF stimulates the production of thromboxane, a potent agent for platelet-aggregation.[2] Additionally, AYPGKF mediates the thrombin-induced release of endostatin from rat platelets.

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)

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Certificates of Analysis (COA)

Lot/Batch Number
036M4719V
055M4706V
123M4724V
013M4749V
082M4726V

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Frederic Lagarrigue et al.
Blood, 136(10), 1180-1190 (2020-06-11)
Ras-related protein 1 (Rap1) is a major convergence point of the platelet-signaling pathways that result in talin-1 binding to the integrin β cytoplasmic domain and consequent integrin activation, platelet aggregation, and effective hemostasis. The nature of the connection between Rap1
Hongyao Xu et al.
The American journal of sports medicine, 48(1), 197-209 (2019-11-26)
Meniscal injury is very common, and injured meniscal tissue has a limited healing ability because of poor vascularity. Platelets contain both pro- and anti-angiogenic factors, which can be released by platelet selective activation. Platelets release a high level of vascular
Seema Bhatlekar et al.
Haematologica, 104(10), 2075-2083 (2019-02-09)
Apoptosis is a recognized limitation to generating large numbers of megakaryocytes in culture. The genes responsible have been rigorously studied in vivo in mice, but are poorly characterized in human culture systems. As CD34-positive (+) cells isolated from human umbilical
Ruth Ann Henriksen et al.
Arteriosclerosis, thrombosis, and vascular biology, 22(5), 861-866 (2002-05-15)
Previous reports have indicated that thrombin-induced thromboxane production by human platelets occurs through two types of interaction between thrombin and the platelet surface. One of these interactions is with protease activated receptor(PAR)-1, the first identified thrombin receptor. These studies were
Matthew T Duvernay et al.
Molecular pharmacology, 91(1), 39-47 (2016-10-28)
Human platelets display a unique dual receptor system for responding to its primary endogenous activator, α-thrombin. Because of the lack of efficacious antagonists, the field has relied on synthetic peptides and pepducins to describe protease-activated receptor PAR1 and PAR4 signaling.
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