Merck
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L2884

Sigma-Aldrich

Leupeptin

microbial, ≥90% (HPLC)

Synonym(s):
Leupeptin hemisulfate salt, Acetyl-Leu-Leu-Arg-al, N-Acetyl-L-leucyl-L-leucyl-L-argininal hemisulfate salt
Linear Formula:
C20H38N6O4 · 1/2H2SO4
CAS Number:
Molecular Weight:
475.59
Numer MDL:
Identyfikator substancji w PubChem:
NACRES:
NA.77

pochodzenie biologiczne

microbial

Poziom jakości

300

próba

≥90% (HPLC)

forma

powder

rozpuszczalność

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

temp. przechowywania

−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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Opis ogólny

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.

Opakowanie

5, 10, 25, 50, 100, 250 mg in glass bottle

Działania biochem./fizjol.

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.)

Komentarz do analizy

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.

Kod klasy składowania

11 - Combustible Solids

WGK

WGK 3

Temperatura zapłonu °F

Not applicable

Temperatura zapłonu °C

Not applicable

Środki ochrony indywidualnej

Eyeshields, Gloves, type N95 (US)

Certificate of Analysis

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Certificate of Origin

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