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A3401

Sigma-Aldrich

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
MDL number:
MFCD00070149
UNSPSC Code:
12352204
PubChem Substance ID:
24890766
NACRES:
NA.32

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.

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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)
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)
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
Ming Li et al.
Ecotoxicology and environmental safety, 135, 24-31 (2016-09-28)
Avermectins (AVMs) are used worldwide in agriculture and veterinary medicine. Residues of avermectin drugs, causing toxicological effects on non-target organisms, have raised great concern. The aim of this study was to investigate the effects of AVM on the expression levels
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Chymotrypsin

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

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