Total synthesis and biological activity of lactacystin, omuralide and analogs

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Abstract

Lactacystin (1) and the related β-lactone omuralide (2) are remarkably selective and potent irreversible inhibitors of the 20 S proteasome, a large polymolecular protein machine which is responsible for the degradation of ubiquitin-labeled proteins. Because of this fact 1 and 2 have emerged as important tools in biochemistry and cell biology. The challenge of synthesis has been accepted by several research groups with the result that 1 and 2 and their analogs can now be synthesized by a variety of synthetic approaches. This review summarizes the synthetic processes which have been developed to date for the production of such compounds. The study of biological activity of analogs of 1 and 2 has clearly defined the structural features which are responsible for the potency of 1 and 2, as described in the closing section of this account. It is concluded that 1 and 2 are nearly optimal for the irreversible inactivation of the 20 S proteasome.

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Corey, E. J., & Li, W. D. Z. (1999). Total synthesis and biological activity of lactacystin, omuralide and analogs. Chemical and Pharmaceutical Bulletin. Pharmaceutical Society of Japan. https://doi.org/10.1248/cpb.47.1

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