34626-51-2Relevant articles and documents
Synthesis of (Z)-5-decenol and (Z)-5-decenyl acetate, components of the sex pheromones of a variety of lepidoptera
Tortajada, Amparo,Mestres, Ramon,Iglesias-Arteaga, Martin A.
, p. 1809 - 1814 (2003)
Two simple Wittig procedures for the synthesis of (Z)-5-decenol and (Z)-5-decenyl acetate based on the monoacetylation or monobromination of 1,5-pentanediol were followed.
Synthesis of (R)-japonilure and (4R,9Z)-9-octadecen-4-olide, pheromones of the Japanese beetle and currant stem girdler
Sabitha, Gowravaram,Bhaskar,Yadagiri,Yadav
, p. 2491 - 2500 (2007)
Asymmetric total synthesis of the sex pheromones of Japanese beetle and currant stem girdler, (R)-japonilure (1) and (4R,9Z)-9-octadecen-4-olide (2), has been achieved. Copyright Taylor & Francis Group, LLC.
Chemoproteomic Evaluation of the Polyacetylene Callyspongynic Acid
Nickel, Sabrina,Serwa, Remigiusz A.,Kaschani, Farnusch,Ninck, Sabrina,Zweerink, Susanne,Tate, Edward W.,Kaiser, Markus
, p. 10721 - 10728 (2015)
Polyacetylenes are a class of alkyne-containing natural products. Although potent bioactivities and thus possible applications as chemical probes have already been reported for some polyacetylenes, insights into the biological activities or molecular mode of action are still rather limited in most cases. To overcome this limitation, we describe the application of the polyacetylene callyspongynic acid in the development of an experimental roadmap for characterizing potential protein targets of alkyne-containing natural products. To this end, we undertook the first chemical synthesis of callyspongynic acid. We then used in situ chemical proteomics methods to demonstrate extensive callyspongynic acid-mediated chemical tagging of endoplasmic reticulum-associated lipid-metabolizing and modifying enzymes. We anticipate that an elucidation of protein targets of natural products may serve as an effective guide to the development of subsequent biological assays that aim to identify chemical phenotypes and bioactivities.
Radical Carbonyl Umpolung Arylation via Dual Nickel Catalysis
Huang, Huan-Ming,Bellotti, Peter,Erchinger, Johannes E.,Paulisch, Tiffany O.,Glorius, Frank
supporting information, p. 1899 - 1909 (2022/02/01)
The formation of carbon-carbon bonds lies at the heart of synthetic organic chemistry and is widely applied to construct complex drugs, polymers, and materials. Despite its importance, catalytic carbonyl arylation remains comparatively underdeveloped, due
Chemical proteomic analysis of palmostatin beta-lactone analogs that affect N-Ras palmitoylation
Cravatt, Benjamin F.,Firestone, Ari J.,Hazeen, Akram,Howell, Amy R.,Luvaga, Irungu K.,Richardson, Stewart K.,Shannon, Kevin,Suciu, Radu M.,Weerasooriya, Chulangani
supporting information, (2021/11/09)
S-Palmitoylation is a reversible post-translational lipid modification that regulates protein trafficking and signaling. The enzymatic depalmitoylation of proteins is inhibited by the beta-lactones Palmostatin M and B, which have been found to target several serine hydrolases. In efforts to better understand the mechanism of action of Palmostatin M, we describe herein the synthesis, chemical proteomic analysis, and functional characterization of analogs of this compound. We identify Palmostatin M analogs that maintain inhibitory activity in N-Ras depalmitoylation assays while displaying complementary reactivity across the serine hydrolase class as measured by activity-based protein profiling. Active Palmostatin M analogs inhibit the recently characterized ABHD17 subfamily of depalmitoylating enzymes, while sparing other candidate depalmitoylases such as LYPLA1 and LYPLA2. These findings improve our understanding of the structure–activity relationship of Palmostatin M and refine the set of serine hydrolase targets relevant to the compound's effects on N-Ras palmitoylation dynamics.
Selective Hydroboration–Oxidation of Terminal Alkenes under Flow Conditions
Elsherbini, Mohamed,Huynh, Florence,Dunbabin, Alice,Allemann, Rudolf K.,Wirth, Thomas
supporting information, p. 11423 - 11425 (2020/08/07)
An efficient flow process for the selective hydroboration and oxidation of different alkenes using 9-borabicyclo(3.3.1)nonane (9-BBN) allows facile conversion in high productivity (1.4 g h?1) of amorpha-4,11-diene to the corresponding alcohol, which is an advanced intermediate in the synthesis of the antimalarial drug artemisinin. The in situ reaction of borane and 1,5-cyclooctadiene using a simple flow generator proved to be a cost efficient solution for the generation of 9-BBN.
