Inspired by the effect of norrisolide on the Golgi complex, we synthesized norrisolide probes that contain: the perhydroindane core of the parent natural product for Golgi localization, a crosslinking unit (aryl azide or epoxide) for covalent binding to the target, and a tag (biotin or iodine) for subsequent target purification. We found that biotin-containing probes 14, 20 and 24 induced inefficient Golgi vesiculation. However, the iodinated probe 25 induced extensive and irreversible Golgi fragmentation. This probe can be used for the isolation of the cellular target of norrisolide.
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| http://dx.doi.org/10.1016/j.bmcl.2006.10.101 | DOI Listing |
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Trifunctional norrisolide probes for the study of Golgi vesiculation.
Bioorg Med Chem Lett
January 2007
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0358, USA.
Inspired by the effect of norrisolide on the Golgi complex, we synthesized norrisolide probes that contain: the perhydroindane core of the parent natural product for Golgi localization, a crosslinking unit (aryl azide or epoxide) for covalent binding to the target, and a tag (biotin or iodine) for subsequent target purification. We found that biotin-containing probes 14, 20 and 24 induced inefficient Golgi vesiculation. However, the iodinated probe 25 induced extensive and irreversible Golgi fragmentation.
View Article and Find Full Text PDFChemical analysis of norrisolide-induced Golgi vesiculation.
J Am Chem Soc
April 2006
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, 92093-0358, USA.
The chemical origin of the norrisolide-induced irreversible Golgi vesiculation was studied using a variety of norrisolide probes. This natural product was found to bind to a receptor on the Golgi membranes using the perhydroindane core fragment as the recognition element. The acetylated gamma-lactol-gamma-lactone side chain of norrisolide is essential for the irreversible Golgi vesiculation and can be replaced by other electrophilic motifs without loss of biological function.
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