Biosynthesis of the salinosporamide A polyketide synthase.
Analysis of S.tropica strains that harbor knockouts of the salinosporamide biosynthetic genes salX and salD, coupled with feeding experiments, revealed that 3-(cyclohex-2-en-1-yl)-2-oxopropanoic acid (60) and 3-(cyclohex-2-en-1-ylidene)-2-oxopropanoic acid (isomers 61 and 62) are important intermediates in the biosynthesis of salinosporamideA, 4, and 8-13.
UC researchers have isolated and characterized one such product, Salinosporamide A (Sal A), which was discovered as a fermentation product from the marine actinomycete Salinispora tropica. By forming an irreversible, covalent adduct with the active site threonine of the 20S subunit of the proteasome, Sal A is able to potently and selectively inhibit all catalytic functions of the proteasome.
Marizomib, also known as ML 858, NPI-0052 and Salinosporamide A, is a potent and selective 20S proteasome inhibitor from natural origin. Marizomib irreversibly inhibits proteasome to overcome compensatory hyperactivation in multiple myeloma and solid tumour patients. Marizomib activity as a single agent in malignant gliomas: ability to cross the blood-brain barrier.
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The second part of this thesis consists of research towards the synthesis of a marine natural product, salinosporamide C, which was discovered in 2002 and has yet to be synthesized. The true activity of the compound is unknown, however its biogenetically related counterpart salinosporamide A is considered a potent 20S proteasome inhibitor.
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