1470-50-4Relevant articles and documents
Mining the Cinnabaramide Biosynthetic Pathway to Generate Novel Proteasome Inhibitors
Rachid, Shwan,Huo, Liujie,Herrmann, Jennifer,Stadler, Marc,Koepcke, Baerbel,Bitzer, Jens,Mueller, Rolf
, p. 922 - 931 (2011)
The cinnabaramides and salinosporamides are mixed PKS/NRPS natural products isolated from a terrestrial streptomycete and a marine actinomycete, respectively. They interfere with the proteasome and thus potentially inhibit the growth of cancer cells. The compounds exhibit a γ-lactam-β-lactone bicyclic ring structure attached to a cyclohexenyl unit and a PKS side chain. As a first step towards improving anticancer activity and permitting genetic approaches to novel analogues, we have cloned and characterized the cinnabaramide biosynthetic genes from Streptomyces sp. JS360. In addition to the expected PKS and NRPS genes, the cluster encodes functionalities for the assembly of the hexyl side chain precursor. The corresponding enzymes exhibit relaxed substrate specificities towards a number of synthesized precursors, enabling production of novel chlorinated cinnabaramides. These were isolated and analyzed for activity, revealing that derivatives bearing a chlorine atom in the PKS side chain show higher inhibitory potentials towards the proteasome's proteolytic subunits (especially the trypsin and chymotrypsin units) and higher cytotoxicities towards human tumor cell lines than the parent cinnabaramide A. Although their activities towards the proteasome were weaker than that of salinosporamide A, the cinnabaramides were found to inhibit the growth of various fungi with greater potency. Copyright
Alpha, beta-unsaturated carbonyl compound production method
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, (2016/11/21)
The present invention relates to an alpha, beta-unsaturated carbonyl compound production method comprising the following steps: (1) oxidizing reaction of a primary alcohol with 3-20 carbon atoms under the effect of an oxidase for selective oxidation of a terminal alcoholic hydroxyl group into an aldehyde group to obtain an aldehyde group compound; (2) Reformatsky reaction of the aldehyde group compound and a halide under the catalytic effect of a metal to produce a corresponding alpha, beta-unsaturated carbonyl compound, the alpha, beta-unsaturated carbonyl compound production method is low-cost, less in environmental pollution, moreover, by alcohol oxidizing reaction by use of the oxidase, the quantitative and high selectivity corresponding alpha, beta-unsaturated carbonyl compound can be obtained, and the after processing is convenient.
Selective heterogeneous palladium-catalyzed hydrogenations of watersoluble alkenes and alkynes
Tour, James M.,Pendalwar, Shekhar L.
, p. 4719 - 4722 (2007/10/02)
Treatment of water-soluble alkenes or alkynes with palladium(II) acetate and triethoxysilane at room temperature afforded the corresponding hydrogenated products in high yields. Simple introduction of a stoichiometric amount of hydrogen is accomplished by using triethoxysilane as the hydrogen source.