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A3401

Sigma-Aldrich

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

protease substrate

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Synonym(s):
H-Ala-Ala-Phe-AMC
Empirical Formula (Hill Notation):
C25H28N4O5
CAS Number:
Molecular Weight:
464.51
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

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

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This Item
M9771S9761B4153
assay

≥98% (TLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

~95%

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

form

powder

form

powder

form

powder

form

powder

General description

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

Substrates

Substrate for chymotrypsin and tripeptidyl peptidaseII.

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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Effect of interfacial properties on the activation volume of adsorbed enzymes
Schuabb V, et al.
Colloids and Surfaces. B, Biointerfaces, 140, 497-504 (2016)
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
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
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)
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)

Articles

Analytical Enzyme Chymotrypsin: Chymotrypsin is produced in the acinar cells of the pancreas as the inactive precursor, chymotrypsinogen.

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