Skip to Content
MilliporeSigma
All Photos(2)

Key Documents

View All Documentation

E3652

Sigma-Aldrich

Epoxomicin

≥95% (HPLC), solid

Synonym(s):

N-Acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-[(1S)-3-methyl-1-[[(2R)-2-methyloxiranyl]carbonyl]butyl]-L-threoninamide

Sign Into View Organizational & Contract Pricing

Select a Size

50 μG
$322.14

$322.14

List price$354.00Save 9%
Web-Only Promotion

Available to ship onApril 08, 2025Details

Request a Bulk Order
All Photos(2)

Select a Size

Change View
50 μG
$322.14

About This Item

CAS Number:
134381-21-8
MDL number:
MFCD03791061
UNSPSC Code:
12352202
PubChem Substance ID:
329799052
NACRES:
NA.77

$322.14

List price$354.00Save 9%
Web-Only Promotion

Available to ship onApril 08, 2025Details

Request a Bulk Order

assay

≥95% (HPLC)

form

solid

Storage temp.

−20°C

SMILES string

CC[C@H](C)[C@H](NC(=O)[C@H]([C@@H](C)CC)N(C)C(C)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(C)C)C(=O)[C@@]1(C)CO1

InChI

1S/C28H50N4O7/c1-11-16(5)21(30-27(38)23(17(6)12-2)32(10)19(8)34)25(36)31-22(18(7)33)26(37)29-20(13-15(3)4)24(35)28(9)14-39-28/h15-18,20-23,33H,11-14H2,1-10H3,(H,29,37)(H,30,38)(H,31,36)/t16-,17-,18+,20-,21-,22-,23-,28+/m0/s1

Inchi Key

DOGIDQKFVLKMLQ-JTHVHQAWSA-N

General description

Epoxomicin is a linear peptide consisting of a threonine or serine residue with α′, β′-epoxyketone derived from leucine or a γ,δ-dehydroleucine.[1] It is a natural product isolated from Actinomyces sp., and is a cell-permeable, potent, selective and irreversible proteasome inhibitor.[2]

Application

Epoxomicin has been used:
  • as an ubiquitin–proteosome system (UPS) inhibitor in pheochromocytoma PC12 cells[3]
  • as a proteasome inhibitor in mammary epithelial MCF-10A cells[4]
  • as a proteasome inhibitor in chymotryptic assay in cardiomyocytes[5]

Biochem/physiol Actions

Epoxomicin binds covalently to the catalytic subunits of proteasome.[2] It forms an adduct with target proteins.[1] It inhibits chymotrypsin-like activity of the proteasome.[6] Epoxomicin also inhibits the nuclear factor κ light chain enhancer of activated B cells (NF-κB) mediated proinflammatory signalling pathway. It is also a potent antitumor and anti-inflammatory agent.[2]
Epoxomicin, a natural product isolated from Actinomyces sp., is a cell-permeable, potent, selective and irreversible proteasome inhibitor.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCV2782
MKCT0881
MKCR3671
MKCQ0771
MKCP8883

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

The selective proteasome inhibitors lactacystin and epoxomicin can be used to either up-or down-regulate antigen presentation at nontoxic doses
Schwarz K, et al.
Journal of Immunology, 164(12), 6147-6157 (2000)
Kyung Bo Kim et al.
Natural product reports, 30(5), 600-604 (2013-04-12)
The initial enthusiasm following the discovery of a pharmacologically active natural product is often fleeting due to the poor prospects for its ultimate clinical application. Despite this, the ever-changing landscape of modern biology has a constant need for molecular probes
Epoxomicin, a potent and selective proteasome inhibitor, exhibits in vivo antiinflammatory activity
Meng L, et al.
Proceedings of the National Academy of Sciences of the USA, 96(18), 10403-10408 (1999)
Differential degradation of full-length and cleaved ataxin-7 fragments in a novel stable inducible SCA7 model
Yu X, et al.
Journal of Molecular Neuroscience, 47(2), 219-233 (2012)
M F Princiotta et al.
Proceedings of the National Academy of Sciences of the United States of America, 98(2), 513-518 (2001-01-10)
The proteasome is the primary protease used by cells for degrading proteins and generating peptide ligands for class I molecules of the major histocompatibility complex. Based on the properties of cells adapted to grow in the presence of the proteasome
View All Related Papers

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service