Leupeptin | CAS 103476-89-7 | Protease Inhibitor | AG Scientific, Inc.

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Leupeptin, Hemisulfate

L-1165
  • CAS: 103476-89-7
  • Formula: C20H38N6O4 • 0.5 H2SO4
  • MW: 475.6 Da
  • Appearance: White powder
  • Purity: >90%

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Leupeptin is a reversible competitive inhibitor of serine and thiol proteases. It has been reported to inhibit calpain, cathepsin B, cathepsins H, L and trypsin. Typical working concentrations are in the range of 10 to 100 µM. Leupeptin appears to be equally effective in any salt form, adjusting for equivalent peptide content. The hemisulfate salts were the first to be commercially available. Of the three salts, the hydrochloride is the least invasive form in biological settings. No problem or preference for the trifluoroacetate (TFA) form has been noted; TFA is volatile, so could possibly be removed by lyophilization.

Microbially produced leupeptin inhibitor was first isolated as a mixture of two very similar forms: acetyl-LeuLeu-Arg-al and propionyl-Leu-Leu-Arg-al. Although the propionyl leupeptin is active as an inhibitor the acetyl form is more commonly used and is available in several different forms. Leupeptin, because of its aldehyde group, may act as a reducing agent and therefore interfere in protein determinations such as Lowry and, to a lesser extent, Bradford.

Leupeptin stock (20 mg/ml): Leupeptin in Methanol. Prepare a stock of 20 mg/ml in methanol, Store at -20°C.

Additional Information

SynonymsAc-Leu-Leu-Arginal; Acetyl-L-leucyl-L-leucyl-L-argininal
Product #L-1165
CAS #103476-89-7
Chemical NameN-acetyl-L-leucyl-N-[4-[(aminoiminomethyl)amino]-1S-formylbutyl]-L-leucinamide, hemisulfate
FormulaC20H38N6O4 • 0.5 H2SO4
MW475.6 Da
AppearanceWhite powder
Purity>90%
SolubilitySoluble in water (50 mg/mL), clear and colorless to faint yellow solution
Storage TempStore desiccated at -20°C

Additional Information

InChIInChI=1S/2C20H38N6O4.H2O4S/c2*1-12(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;1-5(2,3)4/h2*11-13,15-17H,6-10H2,1-5H3,(H,24,28)(H,25,29)(H,26,30)(H4,21,22,23);(H2,1,2,3,4)/t2*15-,16-,17-;/m00./s1
SMILESOS(O)(=O)=O.[H]C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(C)=O.[H]C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(C)=O

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GHS Pictograms
HandlingAvoid contact. Do not get in eyes, on skin, or clothing. Wash thoroughly after handling. Wash contaminated clothing before reuse. Hygroscopic! Protect from light and moisture!

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msds 1L-1165, Leupeptin, SDS, diamond format.pdf
Certificate of Analysis 1L-1165, J1181C.pdf
Certificate of Analysis 2L-1165, J1181B.pdf
Certificate of Analysis 3L-1165, J1181A.pdf
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CitationsKannan, Nivetha, and Vivian W. Tang. "Synaptopodin Couples Epithelial Contractility to a-Actinin-4-Dependent Junction Maturation." The Journal of Cell Biology, vol. 211, no. 2, 26 Oct. 2015, pp. 407-434., doi:10.1083/jcb.201412003.
Tang, Vivian W. "Propagating actomyosin-generated force to intercellular junction." bioRxiv (2017): 191965.
Shneyer, Boris I., Marko Usaj, and Arnon Henn. "Myo19 is an outer mitochondrial membrane motor and effector of starvation-induced filopodia." J Cell Sci. 129.3 (2016): 543-556.\n
Tang, Vivian W., and William M. Brieher. "a-Actinin-4/FSGS1 is required for Arp2/3-dependent actin assembly at the adherens junction." J Cell Biol 196.1 (2012): 115-130.
ReferenceAlpha Actinin-4/FSGS1 is required for Arp2/3-dependent actin assembly at the adherens junction Vivian W. Tang and William M. Brieher
Thermodynamics of A:G mismatch poly(dG) synthesis by human immunodeficiency virus 1 reverse transcriptase.
Soluble HIV Tat Protein Removes the IL-7 Receptor a-Chain from the Surface of Resting CD8 T Cells and Targets It for Degradation
Heat Shock Proteins Regulate Activation-induced Proteasomal Degradation of the Mature Phosphorylated Form of Protein Kinase C. The Journal of Biological Chemistry. Sept. 2013. 288: 27112-27127.
FSGS3/CD2AP is a barbed-end capping protein that stabilizes actin and strengthens adherens junctions. Tang, V. W. and Brieher, W. J. Cell. Biol. Dec 2013. 203: 815-833.
SIGNAL TRANSDUCTION:\n Agonist-induced Down-regulation of Endogenous Protein Kinase C through an Endolysosomal Mechanism\n Michelle A. Lum, Krista E. Pundt, Benjamin E. Paluch, Adrian R. Black, and Jennifer D. Black\n J. Biol. Chem., May 2013; 288: 13093 - 13109.

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