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L2884

Leupeptin

Name: Leupeptin
Brand: SIGMA

powder, ≥90% (HPLC)

Synonym(s):

Leupeptin hemisulfate salt, Acetyl-Leu-Leu-Arg-al, N-Acetyl-L-leucyl-L-leucyl-L-argininal hemisulfate salt

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About This Item

Linear Formula:

C₂₀H₃₈N₆O₄ · 1/2H₂SO₄

CAS Number:

103476-89-7

Molecular Weight:

475.59

UNSPSC Code:

12352202

PubChem Substance ID:

24896328

NACRES:

NA.77

MDL number:

MFCD00037012

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Product Name

Leupeptin, microbial, ≥90% (HPLC)

biological source

microbial

Quality Level

300

assay

≥90% (HPLC)

form

powder

solubility

H₂O: 10 mM (Solutions are stable for a week at 4 °C. Stock solutions are stable up to 6 months at −20 °C.), H₂O: 50 mg/mL

storage temp.

−20°C

SMILES string

OS(O)(=O)=O.CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C=O.CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C=O

InChI

1S/2C20H38N6O4.H2O4S/c2*1-12(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;1-5(2,3)4/h2*11-13,15-17H,6-10H2,1-5H3,(H,24,28)(H,25,29)(H,26,30)(H4,21,22,23);(H2,1,2,3,4)/t2*15-,16-,17-;/m00./s1

InChI key

CIPMKIHUGVGQTG-VFFZMTJFSA-N

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General description

Leupeptin, or N-acetyl-L-leucyl-L-leucyl-L-argininal, is a naturally occurring tripeptide that acts particularly as a serine protease inhibitor and as a cysteine protease inhibitor. Its mechanism of action involves structurally similar covalent binding reactions:

In the active site of serine proteases, leupeptin forms a covalent hemiacetal adduct between the aldehyde group of leupeptin and the hydroxyl group of a serine residue in the enzyme active site.
In the active site of cysteine proteases, the electrophilic (aldehyde) carbon of leupeptin forms a comparable bond with the sulfur atom of a cysteine residue in the enzyme active site.

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.

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number

0000526511

0000438976

0000453303

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ReadyShield Phosphatase and Protease Inhibitor Cocktail FAQ

ReadyShield^® phosphatase and protease inhibitor cocktail FAQ for sample protection in a variety of cell types and tissue extracts, including mammalian, plant, and microbial samples. Our ReadyShield^® Protease Inhibitor Cocktail is a non-freezing solution that contains inhibitors with a broad specificity for serine, cysteine, acid proteases and aminopeptidases.

Global Trade Item Number

SKU	GTIN
L2884-25MG	04061835512683
L2884-.5MG	04061835557486
L2884-10MG	04061835545988
L2884-50MG	04061835557509
L2884-100MG	04061833950487
L2884-1MG	04061835557493
L2884-250MG	04061833950494
L2884-5MG	04061835557516

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