L2884

Leupeptin

powder, ≥90% (HPLC)

• 동의어(들): 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: 103476-89-7
• Molecular Weight: 475.59
• MDL number: MFCD00037012
• UNSPSC 코드: 12352202
• PubChem Substance ID: 24896328
• NACRES: NA.77

속성

• product name: Leupeptin, microbial, ≥90% (HPLC)
• 생물학적 소스: microbial
• Quality Level: 300
• 분석: ≥90% (HPLC)
• 형태: powder
• solubility: 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
• 저장 온도: −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

설명

일반 설명

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.

생화학적/생리학적 작용

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.)

분석 메모

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

안전성 정보

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable
• 개인 보호 장비: Eyeshields, Gloves, type N95 (US)