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62070

Leupeptin

>4000 U/mg

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
NACRES:
NA.77
PubChem Substance ID:
57651875
UNSPSC Code:
12352202
MDL number:
MFCD00037012
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biological source

synthetic

Quality Segment

100

form

powder

specific activity

>4000 U/mg

input

general use sample(s)

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

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.)

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.

Other Notes

1 U corresponds to the amount of inhibitor which reduces the trypsin activity by 1 BAEE-U. (1 BAEE-U is the amount of enzyme which increases the absorbance at 253 nm by 0.001 per minute at pH 7.6 and 25 °C; BAEE, Cat. No. 12880, as substrate)
Inhibitor of trypsin, plasmin, papain and cathepsin B[1][2][3]

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Leupeptin >4000 U/mg

Sigma-Aldrich

62070

Leupeptin

Leupeptin synthetic, ≥85% (HPLC)

Sigma-Aldrich

L8511

Leupeptin

Leupeptin BioUltra, microbial, ≥95% (HPLC)

Sigma-Aldrich

L5793

Leupeptin

Leupeptin hydrochloride microbial, ≥90% (HPLC)

Sigma-Aldrich

L9783

Leupeptin hydrochloride

description

>4000 U/mg

description

synthetic, ≥85% (HPLC)

description

BioUltra, microbial, ≥95% (HPLC)

description

microbial, ≥90% (HPLC)

biological source

synthetic

biological source

synthetic

biological source

microbial

biological source

microbial

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

form

powder

form

powder

form

powder

form

powder

solubility

H2O: 50 mg/mL

solubility

H2O: 50 mg/mL

solubility

H2O: 50 mg/mL

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

specific activity

>4000 U/mg

specific activity

-

specific activity

-

specific activity

-

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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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