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Merck

A3401

Ala-Ala-Phe-7-amido-4-methylcoumarin

protease substrate

Synonym(s):

H-Ala-Ala-Phe-AMC

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About This Item

Empirical Formula (Hill Notation):
C25H28N4O5
CAS Number:
62037-41-6
Molecular Weight:
464.51
NACRES:
NA.32
PubChem Substance ID:
24890766
UNSPSC Code:
12352204
MDL number:
MFCD00070149

Key Documents

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Quality Level

200

assay

≥98% (TLC)

form

powder

solubility

ethanol: 20 mg/mL, clear, colorless to light yellow

storage temp.

2-8°C

SMILES string

CC(N)C(=O)NC(C)C(=O)NC(Cc1ccccc1)C(=O)Nc2ccc3C(C)=CC(=O)Oc3c2

InChI

1S/C25H28N4O5/c1-14-11-22(30)34-21-13-18(9-10-19(14)21)28-25(33)20(12-17-7-5-4-6-8-17)29-24(32)16(3)27-23(31)15(2)26/h4-11,13,15-16,20H,12,26H2,1-3H3,(H,27,31)(H,28,33)(H,29,32)

InChI key

FVRLYIFIDKXFHU-UHFFFAOYSA-N

General description

Substrate for chymotrypsin and tripeptidyl peptidaseII.
Ala-Ala-Phe-7-amido-4-methylcoumarin is a fluorogenic substrate for the proteolytic activity. It is a positively charged substrate molecule.

Application

Ala-Ala-Phe-7-amido-4-methylcoumarin has been used:
  • in the preparation of the reaction mixture for enzymatic assays
  • to initiate the enzyme reaction in tripeptidyl peptidase-1 (TPP1) enzyme activity assay
  • to initiate the assay reaction in lysosomal hydrolases activity assay

Storage Class

11 - Combustible Solids

wgk

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
BCCM0895
BCCH2161
BCCB1732
BCBW2306
BCBS9222V

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Accumulation of polyubiquitylated proteins in response to Ala-Ala-Phe-chloromethylketone is independent of the inhibition of tripeptidyl peptidase II
Villasevil E M, et al.
Biochimica et Biophysica Acta - Molecular Cell Research, 1803(9), 1094-1105 (2010)
R M Bålöw et al.
The Journal of biological chemistry, 261(5), 2409-2417 (1986-02-15)
An extralysosomal tripeptide-releasing aminopeptidase was recently discovered in rat liver (Bålöw, R.-M., Ragnarsson, U., and Zetterqvist, O. (1983) J. Biol. Chem. 258, 11622-11628). In the present work this tripeptidyl peptidase is shown to occur in several rat tissues and in
Raffaella Di Giacopo et al.
Journal of the neurological sciences, 356(1-2), 65-71 (2015-07-06)
This work investigated the molecular cause responsible for a late-onset parkinsonism-dystonia phenotype in three Italian siblings, and clinically characterize this condition. Extensive neurophysiological and neuroradiological exams were performed on the three sibs. Most frequent late-onset metabolic diseases were ruled out
Effect of interfacial properties on the activation volume of adsorbed enzymes
Schuabb V, et al.
Colloids and Surfaces. B, Biointerfaces, 140, 497-504 (2016)
NADPH oxidase promotes Parkinsonian phenotypes by impairing autophagic flux in an mTORC1-independent fashion in a cellular model of Parkinson?s disease
Pal R, et al.
Scientific reports, 6, 22866-22866 (2016)
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