Leupeptin

SIGMA/62070 - >4000 U/mg

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


45-62070-10MG-F	10 mg	$217.00 1/EA	Add To Favorites
45-62070-50MG-F	50 mg	$858.00 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

biological source	synthetic
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	100
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: 50 mg/mL
specific activity	>4000 U/mg
storage temp.	−20°C

Analysis Note:	Leupeptin gives multiple peaks on HPLC due to equilibria among three forms in solution. Purity determined using three main peaks. 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. 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.)
Other Notes:	Inhibitor of trypsin, plasmin, papain and cathepsin B
Unit Definition:	1 U corresponds to the amount of inhibitor which reduces the trypsin activity by 1 BAEE-U. (1 BAEE-U is the amount of enzyme which increases the absorbance at 253 nm by 0.001 per minute at pH 7.6 and 25 °C; BAEE, Cat. No. 12880, as substrate)

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

activity	specific activity: >4000 U/mg
Storage Temp.	−20°C
UNSPSC	12352202

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