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L2023

Leupeptin trifluoroacetate salt

Name: Leupeptin trifluoroacetate salt
Brand: SIGMA

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

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Properties

Product Name

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

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000439786

0000401297

0000395822

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