Inhibitors of the proteasome Sample Clauses

Inhibitors of the proteasome. The importance of the proteasome for viability was capitalized upon by several micro-organisms, demonstrated by the fact that these organisms produce natural products that are capable of blocking the proteasome. For example, the Streptomyces metabolite lactacystin (1)14 is the precursor of the active proteasome inhibitor clasto-lactacystin β- lactone (2),15 also known as ormulide, which is formed under neutral conditions by lactonization (Figure 3). A structurally related proteasome inhibitor salinosporamide A (3, NPI-0052) is produced by Salinispora tropica, a marine bacterium which is found in ocean sediment.16 The mechanism by which these related compounds inhibit the proteasome is through nucleophilic attack of the N-terminal active site threonine of the proteasome on A O OH OH H S O N NH O OH O O Cl O H2N H H O O O N N O O OH NH O O OH Lactacystin (1) Ormulide (2) NH H O O OH Salinosporamide A (3) Belactosin A (4) B Cl O O H H N OH O O O Cl H3N O H H N OH O O O H2N NH H O O OH H H O O H H N H Figure 3. β-lactone containing natural products.
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