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P9273

Sigma-Aldrich

Pro-Phe-Arg-7-amido-4-methylcoumarin

≥95%

Synonym(s):

PFR-Nmec

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About This Item

Empirical Formula (Hill Notation):
C30H37N7O5 · C2H4O2
CAS Number:
65147-21-9
Molecular Weight:
635.71
UNSPSC Code:
12352204
PubChem Substance ID:
24899025
NACRES:
NA.32

Quality Level

200

assay

≥95%

form

powder

composition

Peptide content, ≥65%

solubility

methanol: 50 mg/mL, clear, colorless to faintly yellow

storage temp.

−20°C

SMILES string

NC(NCCC[C@@H](C(NC1=CC=C(C(C)=CC(O2)=O)C2=C1)=O)NC([C@H](CC3=CC=CC=C3)NC(C4NCCC4)=O)=O)=N.CC([O-])=O

InChI

1S/C30H37N7O5.ClH/c1-18-15-26(38)42-25-17-20(11-12-21(18)25)35-28(40)23(10-6-14-34-30(31)32)36-29(41)24(16-19-7-3-2-4-8-19)37-27(39)22-9-5-13-33-22;/h2-4,7-8,11-12,15,17,22-24,33H,5-6,9-10,13-14,16H2,1H3,(H,35,40)(H,36,41)(H,37,39)(H4,31,32,34);1H

InChI key

QYFPUTDFLKFOBA-UHFFFAOYSA-N

Application

Pro-Phe-Arg-7-amido-4-methylcoumarin has been used as fluorogenic substrate:
  • in kinetic experiments to measure the enzymatic activity of factor XII
  • to measure the activity of generated plasma kallikrein using Spectramax plate reader
  • to determine the cathepsin A (CatA) inhibitor selectivity against various proteases using Tecan Safire 2 plate reader

Substrates

A fluorogenic substrate for pancreatic and urinary kallikreins.

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)

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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K Uchida et al.
Biochimica et biophysica acta, 614(2), 501-510 (1980-08-07)
Kallikrein (EC 3.4.21.8) was purified from rat stomach by column chromatography on p-aminobenzamidine-Sepharose, DEAE-Sephadex A-50 and Sephadex G-150 and by isoelectric focusing, measuring its activities to hydrolyse L-prolyl-L-phenylalanyl-L-arginine-4-methyl-coumaryl-7-amide and to release kinin from heat-treated rat plasma. the purified stomach kallikrein
S Paul et al.
Journal of immunology (Baltimore, Md. : 1950), 159(3), 1530-1536 (1997-08-01)
Polyreactive and thyroglobulin (Tg)-directed proteolytic activities present in the serum IgG of healthy controls and patients with autoimmune disease were studied by electrophoretic separation of 125I-labeled Tg reaction products and spectrofluorometric measurement of Pro-Phe-Arg-methylcoumarinamide cleavage at the Arg-methylcoumarinamide bond. A
Sven Ruf et al.
Journal of medicinal chemistry, 55(17), 7636-7649 (2012-08-07)
Cathepsin A (CatA) is a serine carboxypeptidase distributed between lysosomes, cell membrane, and extracellular space. Several peptide hormones including bradykinin and angiotensin I have been described as substrates. Therefore, the inhibition of CatA has the potential for beneficial effects in
K Matsuura et al.
Applied biochemistry and biotechnology, 83(1-3), 107-113 (2000-05-29)
Polyclonal Immunoglobulin (Ig) G from patients with rheumatoid arthritis (RA) and healthy subjects hydrolyzed carbobenzoxy-Val-Gly-Arg p-nitroanilide and D-Pro-Phe-Arg p-nitroanilide. RA IgG exhibited higher activity against the former substrate, but not the latter. On the other hand, RA IgG showed reduced
M Hirado et al.
Advances in experimental medicine and biology, 156, 469-479 (1983-01-01)
For the simple purification of porcine pancreas kallikrein, various affinity chromatographies using L-prolyl-L-phenylalanyl-L-arginine (Pro-Phe-Arg-OH), tosyl-L-arginine (Tos-Arg-OH) and acetyl-L-phenylalanyl-L-arginine (Ac-Phe-Arg-OH) as ligands were examined. The purification was performed as follows using the extract from acetone powder of porcine pancreas as starting
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