Title: Epoxomicin
CAS Registry Number: 134381-21-8
CAS Name: N-Acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-[(1S)-3-methyl-1[[(2R)-2-methyloxiranyl]carbonyl]butyl]-L-threoninamide
Additional Names: BU-4061T
Molecular Formula: C28H50N4O7
Molecular Weight: 554.72
Percent Composition: C 60.63%, H 9.09%, N 10.10%, O 20.19%
Literature References: a¢,b¢-epoxyketone peptide which specifically inhibits proteasome activity. Isoln from actinomycetes: M. Konishi et al., EP 411660; eidem, US 5071957 (both 1991 to Bristol-Myers); and characterization: M. Hanada et al., J. Antibiot. 45, 1746 (1992). Total synthesis: N. Sin et al., Bioorg. Med. Chem. Lett. 9, 2283 (1999). Proteasome selectivity and antiinflammatory activity: L. Meng et al., Proc. Natl. Acad. Sci. USA 96, 10403 (1999). Crystal structure and mechanism of selectivity: M. Groll et al., J. Am. Chem. Soc. 122, 1237 (2000). Use as inhibitor to modulate antigen presentation: K. Schwarz et al., J. Immunol. 164, 6147 (2000).
Properties: Colorless powder, mp 107-109°. [a]D24.5 -66.1 ± 0.4° (c = 0.5 in MeOH). Readily sol in methanol, methylene chloride and ethyl acetate. Practically insol in water.
Melting point: mp 107-109°
Optical Rotation: [a]D24.5 -66.1 ± 0.4° (c = 0.5 in MeOH)
Use: In studies of proteasome biology. |