35378-76-8Relevant articles and documents
Total synthesis of (3Z,9Z,6S,7R) and (3Z,9Z,6R,7S)-6,7-epoxy-3,9-octadecadienes
Xu, Kai,Zhao, Shuai,Xu, Jia-Kuan,Shan, Ming-Wei,Yu, Jia-Li,Wang, Yu-Bo,Zhang, Cheng-Fang,Chen, Xin
, p. 1848 - 1853 (2017)
(3Z,9Z,6S,7R)-6,7-epoxy-3,9-octadecadiene (1) and (3Z,9Z,6R,7S)-6,7-epoxy-3,9-octadecadiene (2) have been stereoselectively synthesized in eight steps from 2-pentyn-1-ol with an overall yield of 8%. The key steps involved the Sharpless asymmetric dihydrox
Identification of a Bromodomain-like Region in 15-Lipoxygenase-1 Explains Its Nuclear Localization
Chen, Deng,Xiao, Zhangping,Guo, Hao,Gogishvili, Dea,Setroikromo, Rita,van der Wouden, Petra E.,Dekker, Frank J.
, p. 21875 - 21883 (2021)
Lipoxygenase (LOX) activity provides oxidative lipid metabolites, which are involved in inflammatory disorders and tumorigenesis. Activity-based probes to detect the activity of LOX enzymes in their cellular context provide opportunities to explore LOX biology and LOX inhibition. Here, we developed Labelox B as a potent covalent LOX inhibitor for one-step activity-based labeling of proteins with LOX activity. Labelox B was used to establish an ELISA-based assay for affinity capture and antibody-based detection of specific LOX isoenzymes. Moreover, Labelox B enabled efficient activity-based labeling of endogenous LOXs in living cells. LOX proved to localize in the nucleus, which was rationalized by identification of a functional bromodomain-like consensus motif in 15-LOX-1. This indicates that 15-LOX-1 is not only involved in oxidative lipid metabolism, but also in chromatin binding, which suggests a potential role in chromatin modifications.
Pheromone Bouquet of the Dried Bean Beetle, Acanthoscelides obtectus (Col.: Chrysomelidae), Now Complete
Vuts, J?zsef,Francke, Wittko,Mori, Kenji,Zarbin, Paulo H. G.,Hooper, Antony M.,Millar, Jocelyn G.,Pickett, John A.,T?th, Mikl?s,Chamberlain, Keith,Caulfield, John C.,Woodcock, Christine M.,Tr?ger, Armin G.,Csonka, éva Bálintné,Birkett, Michael A.
, p. 4843 - 4846 (2015)
Male-specific volatile components, released by the dried bean beetle, Acanthoscelides obtectus, were identified as methyl (E,R)-2,4,5-tetradecatrienoate, methyl (2E,4Z,7Z)-2,4,7-decatrienoate, methyl (2E,4Z)-2,4-decadienoate, octadecanal and the sesquiterpenes (3Z,6E)- and (3E,6E)-α-farnesene. In olfactometer bioassays, pure methyl (E,R)-2,4,5-tetradecatrienoate was only weakly attractive to unmated females. However, a blend of the six identified compounds released in physiologically relevant ratios and doses proved to be as active as headspace odours collected from live males.
A Systematic Study of Unsaturation in Lipid Nanoparticles Leads to Improved mRNA Transfection In Vivo
Lee, Sang M.,Cheng, Qiang,Yu, Xueliang,Liu, Shuai,Johnson, Lindsay T.,Siegwart, Daniel J.
supporting information, p. 5848 - 5853 (2021/02/05)
Lipid nanoparticles (LNPs) represent the leading concept for mRNA delivery. Unsaturated lipids play important roles in nature with potential for mRNA therapeutics, but are difficult to access through chemical synthesis. To systematically study the role of unsaturation, modular reactions were utilized to access a library of 91 amino lipids, enabled by the synthesis of unsaturated thiols. An ionizable lipid series (4A3) emerged from in vitro and in vivo screening, where the 4A3 core with a citronellol-based (Cit) periphery emerged as best. We studied the interaction between LNPs and a model endosomal membrane where 4A3-Cit demonstrated superior lipid fusion over saturated lipids, suggesting its unsaturated tail promotes endosomal escape. Furthermore, 4A3-Cit significantly improved mRNA delivery efficacy in vivo through Selective ORgan Targeting (SORT), resulting in 18-fold increased protein expression over parent LNPs. These findings provide insight into how lipid unsaturation promotes mRNA delivery and demonstrate how lipid mixing can enhance efficacy.
A Modular, Enantioselective Synthesis of Resolvins D3, E1, and Hybrids
Anderson, Edward A.,Elbert, bryony L.,Llaveria, Josep,Streatfeild, penelope E.,Urbitsch, Felix
, (2020/02/28)
Resolvins D3 and E1 are important signaling molecules in the resolution of inflammation. Here, we report a convergent and flexible strategy to prepare these natural products using Hiyama-Denmark coupling of five- and six-membered cyclic alkenylsiloxanes to connect three resolvin fragments, and control the stereochemistry of the natural product (Z)-alkenes. The modular nature of this approach enables the synthesis of novel resolvin hybrids, opening up opportunities for more-extensive investigations of resolvin biology.
Enantioselective Synthesis of 7(S)-Hydroxydocosahexaenoic Acid, a Possible Endogenous Ligand for PPARα
Zhang, Minhao,Sayyad, Ashik A.,Dhesi, Anmol,Orellana, Arturo
, p. 13621 - 13629 (2020/12/15)
We report the first total synthesis of the polyunsaturated fatty acid 7-hydroxydocosahexaenoic acid (7-HDHA) in racemic form and the enantioselective synthesis of 7-(S)-HDHA. Both syntheses follow a convergent approach that unites the C1-C9 and C10-C22 fragments using Sonogashira coupling and Boland reduction as key steps. These syntheses enabled the unambiguous characterization of this natural product for the first time and helped establish 7(S)-HDHA as a possible endogenous ligand for peroxisome proliferator-activated receptor alpha.
A tea canker-worm pheromone (Z, Z, Z) - 3, 6, 9 - triene synthetic method of eighteen carbon (by machine translation)
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, (2018/09/28)
The invention relates to a natural [...] pheromone component novel synthesis method, in particular relates to a tea canker-worm pheromone (Z, Z, Z) - 3, 6, 9 - eighteen carbon triene synthetic method, it has [...], is non-toxic and harmless, which belongs to the field of drug synthesis. The invention uses inexpensive and easily obtained a halopropynyl alcohol as the reaction of the starting material, in order to iodo reagent catalytic coupling reaction as a key step, after six-step reaction, smooth synthetic tea canker-worm pheromone (Z, Z, Z) - 3, 6, 9 - eighteen carbon triene, the operation is simple, low cost, easily obtained and cheap materials, mild reaction conditions, high yield, the large scale preparation. (by machine translation)
Pheromone synthesis. Part 257: Synthesis of methyl (2E,4Z,7Z)-2,4,7-decatrienoate and methyl (E)-2,4,5-tetradecatrienoate, the pheromone components of the male dried bean beetle, Acanthoscelides obtectus (Say)
Mori, Kenji
, p. 5589 - 5596 (2015/08/03)
Tandem Dess-Martin oxidation/Wittig reaction of (2Z,5Z)-2,5-octadien-1-ol yielded methyl (2E,4Z,7Z)-2,4,7-decatrienoate, a newly discovered pheromone component of the male dried bean beetle, while that of (±)-2,3-dodecadien-1-ol gave (±)-methyl (E)-2,4,5-tetradecatrienoate, the racemate of the known and major pheromone component. Methyl (2E,4E,7Z)-2,4,7-decatrienoate was also synthesized, which is the methyl ester of an acid metabolite of a green alga. Reduction of 2,5-octadiyn-1-ol with Zn-Cu/EtOH cleanly gave (2Z,5Z)-2,5-octadien-1-ol.
Synthesis of Rare Polyunsaturated Fatty Acids: Stearidonic and ω-3 Arachidonic
Golovanov,Ivanov,Groza,Myagkova
, p. 1038 - 1041 (2016/02/18)
Total chemical syntheses of the rare natural ω-3 C18 and C20 fatty acids, which possess potential antiinflammatory activity, were elaborated for subsequent studies of their biological activity.
METHODS FOR THE SYNTHESIS OF 13C LABELED DHA AND USE AS A REFERENCE STANDARD
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, (2013/06/05)
A method for preparing 13C labeled docosahexaenoic acid (DHA) represented by Formula A: The method comprises the conversion of 2-pentyn-l-ol to 13C labeled DHA by reaction with propargyl alcohol, 13C labeled propargyl alco
