- Total synthesis of (3Z,9Z,6S,7R) and (3Z,9Z,6R,7S)-6,7-epoxy-3,9-octadecadienes
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(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
- Xu, Kai,Zhao, Shuai,Xu, Jia-Kuan,Shan, Ming-Wei,Yu, Jia-Li,Wang, Yu-Bo,Zhang, Cheng-Fang,Chen, Xin
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Read Online
- Identification of a Bromodomain-like Region in 15-Lipoxygenase-1 Explains Its Nuclear Localization
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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.
- Chen, Deng,Xiao, Zhangping,Guo, Hao,Gogishvili, Dea,Setroikromo, Rita,van der Wouden, Petra E.,Dekker, Frank J.
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Read Online
- Pheromone Bouquet of the Dried Bean Beetle, Acanthoscelides obtectus (Col.: Chrysomelidae), Now Complete
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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.
- 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.
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Read Online
- A Systematic Study of Unsaturation in Lipid Nanoparticles Leads to Improved mRNA Transfection In Vivo
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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.
- Lee, Sang M.,Cheng, Qiang,Yu, Xueliang,Liu, Shuai,Johnson, Lindsay T.,Siegwart, Daniel J.
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supporting information
p. 5848 - 5853
(2021/02/05)
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- A Modular, Enantioselective Synthesis of Resolvins D3, E1, and Hybrids
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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.
- Anderson, Edward A.,Elbert, bryony L.,Llaveria, Josep,Streatfeild, penelope E.,Urbitsch, Felix
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supporting information
(2020/02/28)
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- Enantioselective Synthesis of 7(S)-Hydroxydocosahexaenoic Acid, a Possible Endogenous Ligand for PPARα
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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.
- Zhang, Minhao,Sayyad, Ashik A.,Dhesi, Anmol,Orellana, Arturo
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p. 13621 - 13629
(2020/12/15)
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- A tea canker-worm pheromone (Z, Z, Z) - 3, 6, 9 - triene synthetic method of eighteen carbon (by machine translation)
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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)
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Paragraph 0034; 0035; 0036; 0037; 0038
(2018/09/28)
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- Synthesis of Rare Polyunsaturated Fatty Acids: Stearidonic and ω-3 Arachidonic
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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.
- Golovanov,Ivanov,Groza,Myagkova
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p. 1038 - 1041
(2016/02/18)
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- 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)
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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.
- Mori, Kenji
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p. 5589 - 5596
(2015/08/03)
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- METHODS FOR THE SYNTHESIS OF 13C LABELED DHA AND USE AS A REFERENCE STANDARD
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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
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Page/Page column 18
(2013/06/05)
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- First total synthesis of the anti-inflammatory lipid mediator Resolvin D6
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The first total synthesis of Resolvin D6, an endogenous lipid mediator of resolution of inflammation derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C4 and C17 were generated via an asymmetric Noyori transfer hydrogenation and a Sharpless catalytic asymmetric epoxidation, respectively. A mild copper catalyzed coupling of cis-1,4-dibromo-2-butene with TMS-acetylene generated the C7-C14 fragment. Pd0/CuI Sonogashira couplings and Zn(Cu/Ag) reduction completed the synthesis of Resolvin D6.
- Rodriguez, Ana R.,Spur, Bernd W.
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scheme or table
p. 86 - 89
(2012/01/05)
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- Stereoselective total synthesis of (+)-mueggelone, a novel inhibitor of fish development
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An efficient stereoselective total synthesis of (+)-mueggelone, a novel inhibitor of fish development, is described. Highlights of the strategy include the utilization of Sharpless asymmetric epoxidation, Yamaguchi lactonization and an olefin cross-metathesis as the key steps.
- Yadav,Somaiah,Ravindar,Chandraiah
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p. 2848 - 2850
(2008/09/20)
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- Concise synthesis of (8Z,11Z,14Z)-8,11,14-heptadecatrienal, (7Z,10Z,13Z)-7,10,13-hexadecatrienal, and (8Z,11Z)-8,11-heptadecadienal, components of the essential oil of marine green alga Ulva pertusa
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The long-chain aldehydes, (8Z,11Z,14Z)-8,11,14-heptadecatrienal, (7Z,10Z,13Z)-7,10,13-hexadecatrienal, and (8Z,11Z)-8,11-heptadecadienal, were concisely synthesized by using Grignard coupling, catalytic hydrogenation with the Lindlar catalyst, and oxidation with Dess-Martin periodinane as the key steps. Particularly, (8Z,11Z,14Z)-8,11,14-heptadecatrienal and (7Z,10Z, 13Z)-7,10,13-hexadecatrienal both possessed a seaweed-like odor.
- Akakabe, Yoshihiko,Washizu, Kensuke,Matsui, Kenji,Kajiwara, Tadahiko
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p. 1348 - 1352
(2008/02/01)
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- An Efficient Route to Skipped Diynes and Triynes, (Z,Z) Dienes and (Z,Z,Z) Trienes.
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An efficient route to skipped diynes or triynes, (1Z,4Z) dienes or (1Z,4Z,7Z) trienes is described and illustrated by the synthesis of methyl 5Z,8Z,11Z eicosatrienoate.
- Jeffery, Tuyet,Gueugnot, Sylvie,Linstrumelle, Gerard
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p. 5757 - 5760
(2007/10/02)
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- ISOLATION AND TOTAL SYNTHESIS OF THE MAJOR CONSTITUENT OF THE ROOTS OF CENTAUREA INCANA: APLOTAXENE
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The major constituent of the petroleum ether extract of the root of Centaurea incana was identified as (8Z,11Z,14Z)-1,8,11,14-heptadecatetraene (Aplotaxene 1).A convergent and highly stereoselective synthesis of this compound is reported.
- Cossy, J.,Aclinou, P.
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p. 7615 - 7618
(2007/10/02)
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- STEREOSELECTIVE SYNTHESIS OF (9Z,15Z)-(11S,12S,13S)-11-HYDROXY-12,13-EPOXY OCTADECADIENOIC ACID: A CONSTITUENT OF RICE PLANT INFECTED WITH RICE BLAST DISEASE
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An elegant, stereoselective synthesis of (9Z,15Z)-(11S,12S,13S)-11-hydroxy-12,13-epoxy octadecadienoic acid (1) by enantioselective epoxidation is described.
- Rama Rao, A. V.,Radha Krishna, P.,Yadav, J.S.
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p. 1669 - 1670
(2007/10/02)
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- SYNTHESES OF OPTICALLY ACTIVE PHEROMONES WITH AN EPOXY RING, (+)-DISPARLURE AND BOTH THE ENANTIOMERS OF (3Z,6Z)-cis-9,10-EPOXY-3,6-HENEICOSADIENE
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(+)-Disparlure 1 and both the enantiomers of (3Z,6Z)-cis-9,10-epoxy-3,6-heneicosadiene 2 were synthesized in optically pure forms employing the Sharpless asymmetric epoxidation as the key-step.The natural pheromone 2 isolated from Estigmene acrea was shown to possess (9S,10R)-stereochemistry.
- Mori, Kenji,Ebata, Takashi
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p. 3471 - 3478
(2007/10/02)
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- TOTAL SYNTHESIS OF LEUKOTRIENE B5
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A practical, stereocontrolled synthesis of leukotriene B5 is described which makes this substance readily available for the first time.
- Corey, E. J.,Pyne, Stephen G.,Su, Wei-Gou
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p. 4883 - 4886
(2007/10/02)
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