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L9783

Sigma-Aldrich

Leupeptin hydrochloride

microbial, ≥90% (HPLC)

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Synonym(s):
Acetyl-Leu-Leu-Arg-al hydrochloride
Empirical Formula (Hill Notation):
C20H38N6O4 · HCl
CAS Number:
24125-16-4
Molecular Weight:
463.01
MDL number:
MFCD00133457
UNSPSC Code:
12352202
PubChem Substance ID:
24896529
NACRES:
NA.77

biological source

microbial

Quality Level

200

Assay

≥90% (HPLC)

form

powder

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

Cl.CC(C)CC(NC(C)=O)C(=O)NC(CC(C)C)C(=O)NC(CCCNC(N)=N)C=O

InChI

1S/C20H38N6O4.ClH/c1-12(2)9-16(24-14(5)28)19(30)26-17(10-13(3)4)18(29)25-15(11-27)7-6-8-23-20(21)22;/h11-13,15-17H,6-10H2,1-5H3,(H,24,28)(H,25,29)(H,26,30)(H4,21,22,23);1H

InChI key

OQQYPQNFLLAILR-UHFFFAOYSA-N

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Biochem/physiol Actions

Inhibitor of serine and cysteine proteases. Inhibits plasmin, trypsin, papain, calpain, and cathepsin B. Does not inhibit pepsin, cathepsins A and D, thrombin, or α-chymotrypsin. Effective concentration 10-100 μM. There have been numerous studies using leupeptin to protect against hearing loss caused by acoustic overstimulation or the ototoxic antibiotic gentamicin. (Loss of cochlear hair cells is believed to be mediated by calpain.)

Analysis Note

Leupeptin gives multiple peaks on HPLC because of the formation of tautomeric isomers in solution. Majority of contaminating peptide is racemized leupeptin.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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