The proteasome is a multi-subunit enzyme complex responsible for the degradation of damaged and/or unwanted cellular proteins.  Inhibition of the proteasome can affect multiple signaling pathways within the cell. This in turn results in the disruption of normal homeostatic mechanisms and leads to cell death.  Consequently the proteasome inhibitors may act as anti-cancer agents. Substrate controlled stereoselective alkylation of L-threonine oxazole with functionalized allylic acetates and bromides, provides a-arylidenepyroglutamates, and �-arylpyroglutamates respectively.  The corresponding products were borylated with bis(pinacolato)diboron followed by hydrolysis to provide the chiral pyroglutamate boronic acids.  The synthesized compounds were tested for their ability to inhibit the enzyme proteasome and cell viability on multiple myeloma cancer cell lines.  Our synthetic, characterization, and biological evaluation studies will be presented.

Stereoselective synthesis of chiral borono-pyroglutamates

243rd National Meeting (2012)

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