Leupeptin

SIGMA/L2884 - microbial, ≥90% (HPLC)

Synonym: Leupeptin hemisulfate salt; Acetyl-Leu-Leu-Arg-al; N-Acetyl-L-leucyl-L-leucyl-L-argininal hemisulfate salt

CAS Number: 103476-89-7
Empirical Formula (Hill Notation): C₂₀H₃₈N₆O₄ · 0.5H₂O₄S
Molecular Weight: 475.59
MDL Number: MFCD00037012
Linear Formula: C₂₀H₃₈N₆O₄ · 1/2H₂SO₄
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-L2884-.5MG	0.5 mg	$70.40 1/EA	Add To Favorites
45-L2884-1MG	1 mg	$78.50 1/EA	Add To Favorites
45-L2884-5MG	5 mg	$132.00 1/EA	Add To Favorites
45-L2884-10MG	10 mg	$209.00 1/EA	Add To Favorites
45-L2884-25MG	25 mg	$362.00 1/EA	Add To Favorites
45-L2884-50MG	50 mg	$806.00 1/EA	Add To Favorites
45-L2884-100MG	100 mg	$1020.00 1/EA	Add To Favorites
45-L2884-250MG	250 mg	$2510.00 1/EA	Add To Favorites

Leupeptin is a modified tripeptide. HPLC analysis of leupeptin will show multiple peaks due to tautomeric isomers that exist in solution.

Properties
Descriptions
Safety Info.
Basic Data

assay	≥90% (HPLC)
biological source	microbial
form	powder
InChI	1S/2C20H38N6O4.H2O4S/c21-12(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/h211-13,15-17H,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
InChI key	CIPMKIHUGVGQTG-VFFZMTJFSA-N
Quality Level	300
SMILES string	OS(O)(=O)=O.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.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
solubility	H₂O: 10 mM (Solutions are stable for a week at 4 °C. Stock solutions are stable up to 6 months at −20 °C.)
	H₂O: 50 mg/mL
storage temp.	−20°C

Analysis Note:	Leupeptin gives multiple peaks on HPLC because of the formation of tautomeric isomers in solution. Majority of contaminating peptide is racemized leupeptin.
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.
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.)
General description:	Leupeptin, or N-acetyl-L-leucyl-L-leucyl-L-argininal, is a naturally occurring tripeptide that acts particularly as a serine protease inhibitor and as a cysteine protease inhibitor. Its mechanism of action involves structurally similar covalent binding reactions: • In the active site of serine proteases, leupeptin forms a covalent hemiacetal adduct between the aldehyde group of leupeptin and the hydroxyl group of a serine residue in the enzyme active site. • In the active site of cysteine proteases, the electrophilic (aldehyde) carbon of leupeptin forms a comparable bond with the sulfur atom of a cysteine residue in the enzyme active site.
Packaging:	5, 10, 25, 50, 100, 250 mg in glass bottle

RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	≥90% (HPLC)
Storage Temp.	−20°C
UNSPSC	12352202

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