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Merck

62070

Sigma-Aldrich

Leupeptin

>4000 U/mg

Sinónimos:

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

Fórmula lineal:
C20H38N6O4 · 1/2H2SO4
Número de CAS:
Peso molecular:
475.59
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic

form

powder

specific activity

>4000 U/mg

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

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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.)

Unit Definition

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)

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

Inhibitor of trypsin, plasmin, papain and cathepsin B

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificados de análisis (COA)

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Visite la Librería de documentos

Leupeptins, new protease inhibitors from Actinomycetes.
T Aoyagi et al.
The Journal of antibiotics, 22(6), 283-286 (1969-06-01)
Biological activities of leupeptins.
T Aoyagi et al.
The Journal of antibiotics, 22(11), 558-568 (1969-11-01)
A Kamal et al.
The Journal of cell biology, 142(4), 937-947 (1998-08-29)
Previously we reported that annexin VI is required for the budding of clathrin-coated pits from human fibroblast plasma membranes in vitro. Here we show that annexin VI bound to the NH2-terminal 28-kD portion of membrane spectrin is as effective as
Qianjin Guo et al.
Cell reports, 42(9), 113070-113070 (2023-09-02)
The TMEM127 gene encodes a transmembrane protein of poorly known function that is mutated in pheochromocytomas, neural crest-derived tumors of adrenomedullary cells. Here, we report that, at single-nucleus resolution, TMEM127-mutant tumors share precursor cells and transcription regulatory elements with pheochromocytomas
Structures and activities of protease inhibitors of microbial origin.
H Umezawa
Methods in enzymology, 45, 678-695 (1976-01-01)

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