A substrate for proteasomes
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Ac-Nle-Pro-Nle-Asp-AMC (trifluoroacetate salt)

Item No. 21639

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-acetyl-L-norleucyl-L-prolyl-L-norleucyl-N-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)-L-α-asparagine, trifluoroacetate salt
Synonyms
  • Ac-Nle-Pro-Nle-Asp-7-amido-4-Methylcoumarin
  • Ac-nLPnLD-AMC
Molecular Formula
C33H45N5O9 • XCF3COOH
Formula Weight
655.7
Purity
≥98%
Emission
440-460 nm
Excitation
340-360 nm
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2) (1:3): 0.25 mg/ml
SMILES
O=C1C=C(C2=C(O1)C=C(C=C2)NC([C@@H](NC([C@@H](NC([C@@H]3CCCN3C([C@@H](NC(C)=O)CCCC)=O)=O)CCCC)=O)CC(O)=O)=O)C.OC(C(F)(F)F)=O
InChi Code
InChI=1S/C33H45N5O9.C2HF3O2/c1-5-7-10-23(36-32(45)26-12-9-15-38(26)33(46)24(11-8-6-2)34-20(4)39)30(43)37-25(18-28(40)41)31(44)35-21-13-14-22-19(3)16-29(42)47-27(22)17-21;3-2(4,5)1(6)7/h13-14,16-17,23-26H,5-12,15,18H2,1-4H3,(H,34,39)(H,35,44)(H,36,45)(H,37,43)(H,40,41);(H,6,7)/t23-,24-,25-,26-;/m0./s1
InChi Key
XUTUJUTTZZCAAT-KRZJFFIJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $107

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    1 mg

    $203

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    5 mg

    $740

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    Product Description

    Ac-Nle-Pro-Nle-Asp-AMC is a substrate for proteasomes that is cleaved by the caspase-like site, also known as postglutamyl peptide hydrolase (PGPH), with specific activities of 113 and 6.6 nmol/min/mg by the 26S (rabbit muscle) and 20S (yeast) proteasomes, respectively.1 Caspase-like activity can be quantified by fluorescent detection of free AMC (also known as 7-amino-4-methylcoumarin), which is excited at 340-360 nm and emits at 440-460 nm. Ac-Nle-Pro-Nle-Asp-AMC inhibits the chymotrypsin-like activity of the proteasome allosterically when bound to the caspase-like site.1 It has been used to determine L-DOPA’s (Item No. 13248) effects on protein turnover rates.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kisselev, A.F., Garcia-Calvo, M., Overkleeft, H.S., et al. The caspase-like sites of proteasomes, their substrate specificity, new inhibitors and substrates, and allosteric interactions with the trypsin-like sites. The Journal of Biological Chemisty 278(38), 35869-35877 (2003).

    2. Dunlop, R.A., Dean, R.T., and Rodgers, K.J. The impact of specific oxidized amino acids on protein turnover in J774 cells. Biochem J. 410(1), 131-140 (2008).