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E3652

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

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Size/SKUAvailabilityPrice
50 μg
Please contact Customer Service for Availability
$465.00

About This Item

CAS Number:
134381-21-8
NACRES:
NA.77
PubChem Substance ID:
329799052
UNSPSC Code:
12352202
MDL number:
MFCD03791061
Assay:
≥95% (HPLC)
Form:
solid

$465.00

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Quality Segment

100

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. It is a natural product isolated from Actinomyces sp., and is a cell-permeable, potent, selective and irreversible proteasome inhibitor.

Application

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

Biochem/physiol Actions

Epoxomicin, a natural product isolated from Actinomyces sp., is a cell-permeable, potent, selective and irreversible proteasome inhibitor.
Epoxomicin binds covalently to the catalytic subunits of proteasome. It forms an adduct with target proteins. It inhibits chymotrypsin-like activity of the proteasome. 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.

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This Item
EI8E9661E5161
Epoxomicin ≥95% (HPLC), solid

Sigma-Aldrich

E3652

Epoxomicin

Leupeptin

Sigma-Aldrich

EI8

Leupeptin

Enniatin A from Gnomonia errabunda, ≥95% (HPLC)

Sigma-Aldrich

E9661

Enniatin A

Enniatin A1 from Gnomonia errabunda, ≥95% (HPLC)

Sigma-Aldrich

E5161

Enniatin A1

assay

≥95% (HPLC)

assay

-

assay

≥95% (HPLC)

assay

≥95% (HPLC)

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

200

storage temp.

−20°C

storage temp.

-

storage temp.

−20°C

storage temp.

−20°C

form

solid

form

-

form

-

form

-

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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