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L8511

Leupeptin

Name: Leupeptin
Brand: SIGMA

powder, ≥85% (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:

24896498

NACRES:

NA.77

MDL number:

MFCD00037012

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Properties

Product Name

Leupeptin, synthetic, ≥85% (HPLC)

biological source

synthetic

Quality Level

200

assay

≥85% (HPLC)

form

powder

solubility

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

Description

Application

Leupeptin has been used as a protease inhibitor: in ice-cold lysis buffer to harvest cells for western immunoblotting and immunoprecipitation,in chromatin immunoprecipitation (ChIP) lysis buffer for the isolation of fragmented chromatin samples in lysis buffer I to lyse the cells for tandem affinity purification (TAP)

Biochem/physiol Actions

Leupeptin helps to protect motoneurons from apoptosis. It also helps to enhance muscle function following nerve injury. It possesses neurotrophic action and has a growth-stimulating effect.

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 due to equilibria among three forms in solution. Purity determined using three main peaks. Majority of contaminating peptide is racemized leupeptin.

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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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Global Trade Item Number

SKU	GTIN
L8511-250MG	04061833263662
L8511-25MG	04061833263679
L8511-50MG	04061833263686
L8511-100MG	04061833966044
L8511-10MG	04061833621332
L8511-5MG	04061833966051