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Merck

L0649

Leupeptin hydrochloride

powder, ≥70% (HPLC)

Synonym(s):

Acetyl-Leu-Leu-Arg-al hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C20H38N6O4 · HCl
CAS Number:
24125-16-4
Molecular Weight:
463.01
UNSPSC Code:
12352202
PubChem Substance ID:
24896263
NACRES:
NA.77
MDL number:
MFCD00133457

Product Name

Leupeptin hydrochloride, microbial, ≥70% (HPLC)

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

biological source

microbial

assay

≥70% (HPLC)

form

powder

solubility

water: 50 mg/mL, clear, colorless to yellow

storage temp.

−20°C

Quality Level

200

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Analysis Note

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

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.
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.)

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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Certificates of Analysis (COA)

Lot/Batch Number
0000404429
0000404429
0000334545
0000327302
0000327302

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