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L2023 Sigma-Aldrich

Leupeptin trifluoroacetate salt

≥90% (HPLC), microbial

Synonym: Acetyl-Leu-Leu-Arg-al trifluoroacetate salt

  • CAS Number 147385-61-3

  • Empirical Formula (Hill Notation) C20H38N6O4 · xC2HF3O2

  • Molecular Weight 426.55 (free base basis)

  •  MDL number MFCD00133458

  •  PubChem Substance ID 329817397

  •  NACRES NA.77

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Properties

Related Categories A to C, Aldehydes, Apoptosis Enzymes, Application Index, Biochemicals and Reagents,
Quality Level   200
biological source   microbial
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

Packaging

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

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 due to equilibria among three forms in solution. Purity determined using three main peaks. Majority of contaminating peptide is racemized leupeptin.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Meet Synthia - Retrosynthesis Sofware
Protocols & Articles
Peer-Reviewed Papers
15

References

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