A fluorogenic substrate for the 26S proteasome
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Ac-RLR-AMC (trifluoroacetate salt)

Item No. 26643

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(S)-2-acetamido-5-guanidino-N-((S)-1-(((S)-5-guanidino-1-((4-methyl-2-oxo-2H-chromen-7-yl)amino)-1-oxopentan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)pentanamide, 2,2,2-trifluoroacetate salt
Synonyms
  • Ac-Arg-Leu-Arg-AMC
  • Ac-Arg-Leu-Arg-7-amino-4-Methylcoumarin
Molecular Formula
C30H46N10O6 • XCF3COOH
Formula Weight
642.8
Purity
≥98%
Emission
440-460 nm
Excitation
380 nm
Formulation (Request formulation change)
A lyophilized solid
Solubility(Learn about Variance in Solubility)
Acetic Acid (5%): Soluble
λmax
231, 296, 328 nm
SMILES
CC(C1=CC=C(NC([C@@H](NC([C@H](CC(C)C)NC([C@@H](NC(C)=O)CCCNC(N)=N)=O)=O)CCCNC(N)=N)=O)C=C1O2)=CC2=O.OC(C(F)(F)F)=O
InChi Code
InChI=1S/C30H46N10O6.C2HF3O2/c1-16(2)13-23(40-27(44)21(37-18(4)41)7-5-11-35-29(31)32)28(45)39-22(8-6-12-36-30(33)34)26(43)38-19-9-10-20-17(3)14-25(42)46-24(20)15-19;3-2(4,5)1(6)7/h9-10,14-16,21-23H,5-8,11-13H2,1-4H3,(H,37,41)(H,38,43)(H,39,45)(H,40,44)(H4,31,32,35)(H4,33,34,36);(H,6,7)/t21-,22-,23-;/m0./s1
InChi Key
CEEMPRHZPRGAAK-RGRVRPFLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $69

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    5 mg

    $280

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    Product Description

    Ac-RLR-AMC is a fluorogenic substrate for the 26S proteasome.1,2 Upon cleavage, 7-amino-4-methylcoumarin (AMC) is released and its fluorescence can be used to quantify the trypsin-like activity of 26S proteasomes. AMC displays excitation/emission maxima of 380/440-460 nm, respectively.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kisselev, A.F., and Goldberg, A.L. Monitoring activity and inhibition of 26S proteasomes with fluorogenic peptide substrates. Methods Enzymol. 398, 364-378 (2005).

    2. Vilchez, D., Morantte, I., Liu, Z., et al. RPN-6 determines C. elegans longevity under proteotoxic stress conditions. Nature 489(7415), 263-268 (2012).

    Product Citations

    Rana, P.S., Ignatz-Hoover, J.J., Guo, C., et al. Immunoproteasome activation expands the MHC Class I immunopeptidome, unmasks neoantigens, and enhances T-cell anti-myeloma activity. Mol. Cancer Ther. 23(12), 1743-1760 (2024).