L2884

Leupeptin

powder, ≥90% (HPLC)

• Szinonimák: Leupeptin hemisulfate salt, Acetyl-Leu-Leu-Arg-al, N-Acetyl-L-leucyl-L-leucyl-L-argininal hemisulfate salt
• Lineáris képlet: C₂₀H₃₈N₆O₄ · 1/2H₂SO₄
• CAS-szám: 103476-89-7
• Molekulatömeg: 475.59
• MDL-szám: MFCD00037012
• UNSPSC kód: 12352202
• PubChem Substance ID: 24896328
• NACRES: NA.77

Tulajdonságok

• product name: Leupeptin, microbial, ≥90% (HPLC)
• biológiai forrás: microbial
• Minőségi szint: 300
• Teszt: ≥90% (HPLC)
• form: powder
• oldhatóság: 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
• tárolási hőmérséklet: −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
• Nemzetközi kémiai azonosító kulcs: CIPMKIHUGVGQTG-VFFZMTJFSA-N

Leírás

Általános leírás

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.

Biokémiai/fiziológiai hatások

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.)

Analízis megjegyzés

Leupeptin gives multiple peaks on HPLC because of the formation of tautomeric isomers in solution. Majority of contaminating peptide is racemized leupeptin.

Biztonsági adatok

• Tárolási osztály kódja: 11 - Combustible Solids
• WGK: WGK 3
• Lobbanási pont (F): Not applicable
• Lobbanási pont (C): Not applicable
• Egyéni védőeszköz: Eyeshields, Gloves, type N95 (US)