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L2023

Sigma-Aldrich

Leupeptin trifluoroacetate salt

≥90% (HPLC), microbial

Synonym(s):

Acetyl-Leu-Leu-Arg-al trifluoroacetate salt

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About This Item

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

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

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.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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