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L2145

Sigma-Aldrich

L-Leucine-7-amido-4-methylcoumarin hydrochloride

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Synonym(s):
H-L-Leu-AMC HCl
Empirical Formula (Hill Notation):
C16H20N2O3 · HCl
CAS Number:
Molecular Weight:
324.80
MDL number:
PubChem Substance ID:
NACRES:
NA.32

assay

≥98% (TLC)

Quality Level

form

powder

solubility

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

fluorescence

λex 327 nm; λem 349 nm (pH 8.0)
λex 380 nm; λem 440 nm (Reaction product)

storage temp.

−20°C

SMILES string

Cl.CC(C)C[C@H](N)C(=O)Nc1ccc2C(C)=CC(=O)Oc2c1

InChI

1S/C16H20N2O3.ClH/c1-9(2)6-13(17)16(20)18-11-4-5-12-10(3)7-15(19)21-14(12)8-11;/h4-5,7-9,13H,6,17H2,1-3H3,(H,18,20);1H/t13-;/m0./s1

InChI key

VCRXITKKWBOQRZ-ZOWNYOTGSA-N

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This Item
A3401B4153L2158
solubility

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

solubility

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

solubility

methanol: 50 mg/mL, clear, colorless

solubility

water: 25 mg/mL

form

powder

form

powder

form

powder

form

powder

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

fluorescence

λex 327 nm; λem 349 nm (pH 8.0)

fluorescence

-

fluorescence

-

fluorescence

-

General description

L-Leucine-7-amido-4-methylcoumarin hydrochloride (Leu-AMC) is a fluorogenic peptidyl substrate for leucine aminopeptidase, an extracellular enzyme found abundantly in natural aquatic systems. This enzyme is one of the various enzymes used by bacteria for protein hydrolysis.

Application

L-Leucine-7-amido-4-methylcoumarin hydrochloride (Leu-AMC) as a substrate analog to determine leucine aminopeptidase activity
L-Leucine-7-amido-4-methylcoumarin hydrochloride has been used:
  • as a substrate in fluorescence-based soil assays
  • to determine leucine aminopeptidase activity of both Plasmodium falciparum M1 (PfA-M1) and PfA-M17 enzymes

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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Penton CR and Newman S
Biogeochemistry, 84, 83-98 (2007)
Jisook Lee et al.
ChemMedChem, 16(1), 234-249 (2020-09-19)
Aminopeptidase N (APN/CD13) is a zinc-dependent ubiquitous transmembrane ectoenzyme that is widely present in different types of cells. APN is one of the most extensively studied metalloaminopeptidases as an anti-cancer target due to its significant role in the regulation of
M17 leucine aminopeptidase of the human malaria parasite Plasmodium vivax
Lee JY, et al.
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Acanthamoeba are a free-living protozoan whose pathogenic strain can cause severe human diseases, such as granulomatous encephalitis and keratitis. As such, the pathogenic mechanism between humans and Acanthamoeba is still unknown. In our previous study, we identified the secreted Acanthamoeba

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