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Merck
CN

L2023

Leupeptin trifluoroacetate salt

powder, ≥90% (HPLC)

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)
UNSPSC Code:
12352202
PubChem Substance ID:
329817397
NACRES:
NA.77
MDL number:
MFCD00133458

Key Documents

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Product Name

Leupeptin trifluoroacetate salt, ≥90% (HPLC), microbial

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

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

Quality Level

200

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.)
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.

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000439786
0000439786
0000401297
0000401297
0000395822

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Javier Manzano-Lopez et al.
PloS one, 17(2), e0263617-e0263617 (2022-02-11)
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
Maryam Amirazodi et al.
Iranian journal of basic medical sciences, 25(2), 254-262 (2022-06-04)
High-intensity interval training (HIIT) is a shape of interval training that provides ameliorated athletic capacity and has a good effect on health. Resveratrol is a natural polyphenol abundant in grapes and red wine and has been demonstrated to apply various
John Cherrington Carmen et al.
Frontiers in microbiology, 2, 1-1 (2011-07-01)
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
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
Cellular expression and antimicrobial function of a phylogenetically conserved novel histone 1x-like protein on mouse cells: a potential new class of pattern recognition receptor.
Evans, D.L., et al.
Journal of Neurochemistry, 86, 133-141 (2009)
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