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L2023

Sigma-Aldrich

Leupeptin trifluoroacetate salt

≥90% (HPLC), microbial

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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
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

Related Categories

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

Regulatory Information

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Alexandra Weyrich et al.
Biochemistry and cell biology = Biochimie et biologie cellulaire, 86(5), 380-385 (2008-10-17)
It is controversial whether DNA methylation plays a functional role in Drosophila. We have studied testis DNA of Drosophila melanogaster Meigen, 1830 with antisera against 5-methylcytosine (5mC) and found no evidence for the presence of significant amounts of 5mC. Reactions
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Intracellular trafficking through the secretory organelles depends on transient interactions between cargo proteins and transport machinery. Cytosolic coat protein complexes capture specific luminal cargo proteins for incorporation into transport vesicles by interacting with them indirectly through a transmembrane adaptor or
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The regulation of mitochondrial permeability, a key event in the initiation of apoptosis is governed by the opposing actions of the pro- and anti-apoptotic members of the BCL2-family of proteins. The BCL2-family can be classified further based on the number
N Korn et al.
Poultry science, 81(7), 1077-1085 (2002-08-07)
A monoclonal antibody (4C7/2E4) that binds to an antigen located on the midpiece of turkey spermatozoa has been produced and characterized. The antibody was also reactive to antigens on the midpiece of chicken, Japanese quail, and bobwhite quail spermatozoa but
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