Boc-D-FMK

• CAT Number: R061596
• CAS Number: 187389-53-3
• Molecular Formula: C11H18FNO5
• Molecular Weight: 263.265
• Purity: ≥95%
• Synonyms: (3S)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-5-fluoro-4-oxo-pentanoic acid methyl ester; (S)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-5-fluoro-4-oxo-pentanoic acid methyl ester; BAF; Boc-Asp(OMe)-FMK; Boc-Asp(OMe)-fluoromethylketone; BocD.fmk
• Storage: -20°C
• IUPAC Name: methyl (3S)-5-fluoro-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxopentanoate
• InChI: InChI=1S/C11H18FNO5/c1-11(2,3)18-10(16)13-7(8(14)6-12)5-9(15)17-4/h7H,5-6H2,1-4H3,(H,13,16)/t7-/m0/s1
• InChIKey: MXOOUCRHWJYCAL-ZETCQYMHSA-N
• SMILES: CC(C)(C)OC(=O)NC(CC(=O)OC)C(=O)CF

Boc-<wbr></wbr>D-<wbr></wbr>FMK is a cell-<wbr></wbr>permeable, irreversible pan-<wbr></wbr>caspase inhibitor. Also known as Boc-<wbr></wbr>D(OMe)-<wbr></wbr>FMK, this compound contains a methyl ester group, which facilitates uptake by cells and subsequently is removed by cytoplasmic esterases, leaving the functional inhibitor. Boc-<wbr></wbr>D-<wbr></wbr>FMK blocks apoptosis stimulated by TNF-<wbr></wbr>α in neutrophils (IC50 = 39 µM), by bile duct ligation in hepatocytes, and by TNF-<wbr></wbr>α in renal endothelial cells. The FMK pharmacophore is known to interact with non-<wbr></wbr>caspase cysteine proteases, presumably explaining why Boc-<wbr></wbr>D-<wbr></wbr>FMK also inhibits cathepsins H and L.