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Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication. It blocks the cell cycle at early S phase . It is a specific inhibitor of DNA polymerase Alpha and Delta in eukaryotic cells and in some viruses ( vaccinia [ 1 ] [ 2 ] and herpesviruses ) and an apoptosis inducer in HeLa cells.
Aphidicolin is a mycotoxin originally known to be produced by the fungus, Cephalosporium aphidicola. This antiviral compound was isolated in mycelium culture filtrate of N. sphaerica. [11] Epoxyexserophilone is a metabolite similar to the phytotoxin, exserohilone. Fermentation of N. sphaerica led to the production of epoxyexserophilone.
Aphidicolan-16β-ol synthase (EC 4.2.3.42, PbACS) is an enzyme with systematic name 9α-copalyl-diphosphate diphosphate-lyase (aphidicolan-16β-ol-forming). [1] [2] This enzyme catalyses the following chemical reaction
A synthesis of Aphidicolin use methodology around the vinylcyclopropane rearrangement developed in their own laboratory . [40] A key step converts a late stage siloxyvinylcyclopropane into a cyclopentene that contained the [6-6-5]-fused carbon skeleton found within the natural product.
In some experiments, a researcher may want to control and synchronize the time when a group of cells progress to the next phase of the cell cycle. [5] The cells can be induced to arrest as they arrive (at different time points) at a certain phase, so that when the arrest is lifted (for instance, rescuing cell cycle progression by introducing another chemical) all the cells resume cell cycle ...
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Robert Ireland's synthesis of (±)-aphidicolin uses the Wolff rearrangement to do a tandem ring-contraction, and [2 + 2] cycloaddition. [38] Synthesis of (±)-aphidicolin. The Danheiser benzannulation photolyses α-diazo ketones and traps with an alkyne, which undergoes a pericyclic cascade, to ultimately form versatilely substituted phenols. [39]
Holton’s research group has accomplished the total synthesis of several natural products. Most notable are prostaglandin F 2α, narwedine, aphidicolin, taxusin, Taxol and hemibrevetoxin B. Holton is Chief Scientific Officer, a director and co-founder of Taxolog, Inc, and president and founder of MDS Research Foundation and Syncure, Inc.