L2023

Leupeptin trifluoroacetate salt

≥90% (HPLC), microbial

• Synonym(s): Acetyl-Leu-Leu-Arg-al trifluoroacetate salt
• Empirical Formula (Hill Notation): C₂₀H₃₈N₆O₄ · xC₂HF₃O₂
• CAS Number: 147385-61-3
• Molecular Weight: 426.55 (free base basis)
• MDL number: MFCD00133458
• UNSPSC Code: 12352202
• PubChem Substance ID: 329817397
• NACRES: NA.77

Properties

• biological source: microbial
• Quality Level: 200
• Assay: ≥90% (HPLC)
• form: powder
• solubility: H₂O: 10 mM (Solutions are stable only a few hours. Stock solutions are stable up to 6 months at −20 °C.)
• storage temp.: −20°C
• SMILES string: OC(=O)C(F)(F)F.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/C20H38N6O4.C2HF3O2/c1-12(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;3-2(4,5)1(6)7/h11-13,15-17H,6-10H2,1-5H3,(H,24,28)(H,25,29)(H,26,30)(H4,21,22,23);(H,6,7)/t15-,16-,17-;/m0./s1
• InChI key: WUHGBZVQELGOMH-FRKSIBALSA-N

Description

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.)

Analysis Note

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

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves