- LIPIDS FROM THE BROWN ALGA CYSTOSEIRA BARBATA
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Two new diunsaturated lipids, related to palmitic acid, were isolated from the brown alga Cystoseira barbata, one of which is toxic to mice during P388 lymphocytic leukemia tests. Key Word Index - Cystoseira barbata; Phaeophyceae; brown alga, ethyl-(Z),(Z)-hexadec-10,13-dienate; (Z),(Z)-hexadec-10,13-dienal.
- Banaigs, Bernard,Francisco, Christian,Gonzales, Emmanuel,Codomier, Louis
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- Photoaffinity probes for nematode pheromone receptor identification
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Identification of pheromone receptors plays a central role for uncovering signaling pathways that underlie chemical communication in animals. Here, we describe the synthesis and bioactivity of photoaffinity probes for the ascaroside ascrNo.8, a sex-pheromone of the model nematode, Caenorhabditis elegans. Structure-activity studies guided incorporation of alkyne- and diazirine-moieties and revealed that addition of functionality in the sidechain of ascrNo.8 was well tolerated, whereas modifications to the ascarylose moiety resulted in loss of biological activity. Our study will guide future probe design and provides a basis for pheromone receptor identification via photoaffinity labeling in C. elegans.
- Zhang, Ying K.,Reilly, Douglas K.,Yu, Jingfang,Srinivasan, Jagan,Schroeder, Frank C.
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- Silica-Mediated Monohydrolysis of Dicarboxylic Esters
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A new method for the monohydrolysis of dicarboxylic esters is presented, involving as key step a silanolysis at elevated temperatures at the silica gel surface. In the second step, the surface bound silyl esters are cleaved off under mild conditions, giving a straightforward and fast access to half esters. Based on recovered starting material generally yields well above 70 % are achieved, both, with stiff aromatic as well as flexible aliphatic substrates, as long as the ester groups involved are remote enough from each other. Otherwise competing reactions are becoming determinative, anhydride formation in the case of phthalates and decarbonylative fragmentation in the case of malonates. The new method was also successfully tested on a multigram scale with a minimalistic apparatus setup.
- Dyker, Gerald
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supporting information
p. 6773 - 6776
(2021/12/31)
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- Synthetic method of acid compound
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The invention belongs to the field of organic synthesis, and particularly relates to a synthetic method of an acid compound. An acid anhydride compound and an alkyl bromide or a functionalized alkyl bromide are subjected to a cross-electrophilic coupling reaction to synthesize an acid compound, so that the application of the alkyl bromide in the cross-electrophilic coupling reaction is expanded, and a novel non-traditional method for chemically and selectively constructing a carbon-carbon bond through a decarburization process is provided. The synthesis method is simple, economic, green and environment-friendly, and has wider applicability or is suitable for large-scale production.
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Paragraph 0028-0032; 0054
(2020/08/25)
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- CATIONIC LIPID
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The present invention provides a cationic lipid which can be utilized for nucleic acid delivery into the cytoplasm. The cationic lipid of the present invention is, for example, a compound represented by the following Formula (1) or a pharmaceutically acceptable salt thereof.
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Paragraph 0058; 0059
(2017/11/17)
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- Synthesis of fluorescent carboxylic acid ligands for construction of monolayers on nanostructures
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Two new long-chain carboxylic acids (1, 2) bearing strong fluorescent group pyrene as ligands for Self-Assembled Monolayers (SAMs) have been synthesized. The multistep targeted synthesis is accomplished by use of Pyren-1-yl methylamine hydrochloride and employing simplified synthetic protocols. Compound 2 contains a chiral center purposely introduced along the atom chain in order to make it suitable for chiro-optical studies of the resulting SAMs.
- Jadhav, Sushilkumar A.
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p. 1640 - 1646,7
(2020/09/09)
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- Influence of positional isomers on the macroscale and nanoscale architectures of aggregates of racemic hydroxyoctadecanoic acids in their molecular gel, dispersion, and solid states
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Inter/intramolecular hydrogen bonding of a series of hydroxystearic acids (HSAs) are investigated. Self-assembly of molecular gels obtained from these fatty acids with isomeric hydroxyl groups is influenced by the position of the secondary hydroxyl group. 2-Hydroxystearic acid (2HSA) does not form a molecular dimer, as indicated by FT-IR, and growth along the secondary axis is inhibited because the secondary hydroxyl group is unable to form intermolecular H-bonds. As well, the XRD long spacing is shorter than the dimer length of hydroxystearic acid. 3-Hydroxystearic acid (3HSA) forms an acyclic dimer, and the hydroxyl groups are unable to hydrogen bond, preventing the crystal structure from growing along the secondary axis. Finally, isomers 6HSA, 8HSA, 10HSA, 12HSA, and 14HSA have similar XRD and FT-IR patterns, suggesting that these molecules all self-assemble in a similar fashion. The monomers form a carboxylic cyclic dimer, and the secondary hydroxyl group promotes growth along the secondary axis.
- Abraham, Shibu,Lan, Yaqi,Lam, Ricky S. H.,Grahame, Douglas A. S.,Kim, Jennifer Jae Hee,Weiss, Richard G.,Rogers, Michael A.
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experimental part
p. 4955 - 4964
(2012/07/13)
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- Synthesis and anti-cancer activity of C-ring-functionalized prodigiosin analogues
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Prodigiosin is the parent member of the 4-methoxypyrrolyldipyrromethene family of natural products and is known for its anti-cancer activity. A new series of analogues was synthesized, incorporating pendent functional esters and β-carbonyl substituents on the C-ring. The β-carbonyl group allowed for the facile isolation of the prodigiosenes, and the pendent esters allow for further derivatization. The novel prodigiosenes generally retain the anti-cancer activity of prodigiosin in 60 human cell lines derived from nine cancer cell types, with neither the conjugated /3-carbonyl group, as either ketone or ester, nor the pendent ester significantly reducing the anti-cancer activity of the core skeleton.
- Regourd, Jasmine,Ali, Adeeb Al-Sheikh,Thompson, Alison
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p. 1528 - 1536
(2008/02/02)
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- Process for producing ferrocenoyl derivatives
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Disclosed is a process for producing a ferrocenoyl derivative comprising the reaction of ferrocene derivative with monocarboxylic acid or dicarboxylic acid in the presence of a catalyst. The ferrocenoyl derivative obtained by said process is very useful as the intermediate product for various functional materials, among all, for the micelle forming agents (surfactants) in so-called Micellar Disruption Method or the intermediate product of it.
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- SYNTHESE BIOLOGISCH AKTIVER UNGESAETTIGTER AMIDE
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The synthesis of seven naturally occurring unsaturated amides is described.
- Bohlmann, Ferdinand,Ganzer, Michael,Krueger, Martin,Nordhoff, Erhard
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p. 123 - 128
(2007/10/02)
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- Liposomal Membranes. 2. Synthesis of a Novel Pyrene-Labeled Lecithin and Structural Studies on Liposomal Bilayers
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A novel pyrene-labeled phosphatidylcholine, 1,2-bis-sn-glycero-3-phosphorylcholine (DPDL), was synthesized for use in structural studies on the liposomal bilayers.From the fluorescence measurements on DPDL incorporated into the phospholipid bilayers as well as in organic solvents and aqueous buffered solutions, the following interesting information was obtained. (1) The probe DPDL is intercalated in a well-ordered fashion in the very hydrophobic domain of egg and dipalmitoylphosphatidylcholine bilayers. (2) Without cholesterol and /or below the phase-transition temperature, DPDL is arranged with the lipid-separated conformation in the shrunk liposomal bilayers (Figure 9d). (3) Increasing the mobility of lipid molecules by the addition of cholesterol and/or by elevating temperatures causes a conformational change of DPDL in the bilayers from the lipid-separated conformation to the intimate one (Figure 9c).
- Sunamoto, Junzo,Kondo, Hiroki,Nomura, Tadashi,Okamoto, Hiroshi
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p. 1146 - 1152
(2007/10/02)
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