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A3401

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

Name: Ala-Ala-Phe-7-amido-4-methylcoumarin
Brand: SIGMA

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

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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

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

Substrate for chymotrypsin and tripeptidyl peptidaseII.

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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Effect of interfacial properties on the activation volume of adsorbed enzymes

Schuabb V, et al.

Colloids and Surfaces. B, Biointerfaces, 140, 497-504 (2016)

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)

Upregulation of tripeptidyl-peptidase 1 by 3-hydroxy-(2,2)-dimethyl butyrate, a brain endogenous ligand of PPARα: Implications for late-infantile Batten disease therapy.

Sudipta Chakrabarti et al.

Neurobiology of disease, 127, 362-373 (2019-04-01)

The late-infantile Batten disease or late-infantile neuronal ceroid lipofuscinosis (LINCL) is an autosomal recessive lysosomal storage disorder caused by mutations in the Cln2 gene leading to deficiency of lysosomal enzyme tripeptidyl peptidase 1 (TPP1). At present, available options for this

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)

Characteristics of PPT1 and TPP1 enzymes in neuronal ceroid lipofuscinosis (NCL) 1 and 2 by dried blood spots (DBS) and leukocytes and their application to newborn screening.

Rina Itagaki et al.

Molecular genetics and metabolism, 124(1), 64-70 (2018-03-31)

We first characterized PPT1 and TPP1 enzymes in dried blood spots (DBS), plasma/serum, and leukocytes/lymphocytes using neuronal ceroid lipofuscinosis (NCL) 1 and 2 patients and control subjects. PPT1 enzyme had only one acid form in control DBS, plasma/serum, and leukocytes/lymphocytes

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Articles

Chymotrypsin

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

Global Trade Item Number

SKU	GTIN
A3401-25MG	04061832904146

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