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E3652

Epoxomicin

Name: Epoxomicin
Brand: SIGMA

≥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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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

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Properties

Quality Level

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

Description

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.

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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