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Search for "fatty acids" in Full Text gives 77 result(s) in Beilstein Journal of Organic Chemistry.

Synthesis and in vitro biochemical evaluation of oxime bond-linked daunorubicin–GnRH-III conjugates developed for targeted drug delivery

  • Sabine Schuster,
  • Beáta Biri-Kovács,
  • Bálint Szeder,
  • Viktor Farkas,
  • László Buday,
  • Zsuzsanna Szabó,
  • Gábor Halmos and
  • Gábor Mező

Beilstein J. Org. Chem. 2018, 14, 756–771, doi:10.3762/bjoc.14.64

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  • breast adenocarcinoma cancer cells (MCF-7) and on hormone independent human colon carcinoma cells (HT-29) were analyzed [22][25][27][28]. Thereby, it has been exposed, that an exchange of 4Ser by 4Lys followed by acylation of the ε-amino group with short chain fatty acids (SCFA) improved the cellular
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Published 04 Apr 2018

Latest development in the synthesis of ursodeoxycholic acid (UDCA): a critical review

  • Fabio Tonin and
  • Isabel W. C. E. Arends

Beilstein J. Org. Chem. 2018, 14, 470–483, doi:10.3762/bjoc.14.33

Graphical Abstract
  • ]. In order to extract and purify the different bile acids, bile is frozen and lyophilized: from 100 mL of bile 8 g of dry powder can be obtained. From these about 6.9 g of 90% pure bile acids can be obtained [27]. Cholesterol, cholesterol esters, triglycerides and free fatty acids are selectively
  • used for the hydrogenation of fatty acids). In comparison to the Wolff–Kishner reaction, the use of hydrazine is replaced by the use of hydrogen gas, which can be seen as a double-bladed knife. The reduction step can also be performed with NaBH4 or other reductants. At the moment, a complete and clear
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Published 20 Feb 2018

Aminosugar-based immunomodulator lipid A: synthetic approaches

  • Alla Zamyatina

Beilstein J. Org. Chem. 2018, 14, 25–53, doi:10.3762/bjoc.14.3

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  • chemical structure of lipid A is based on the β(1→6)-linked 1-,4′-bisphosphorylated diglucosamine backbone which is typically tetra- till heptaacylated at the amino groups (positions 2 and 2’) and hydroxyl groups (positions 3 and 3’) by (R)-3-hydroxy- or/and (R)-3-acyloxyacyl fatty acids of variable
  • chain β-hydroxy fatty acids, anomeric phosphorylation and the synthesis of binary glycosyl phosphodiesters involving two amino sugars. Explicit structure–activity relationships data obtained with synthetic lipid A derivatives would also help to design novel therapeutic approaches for sepsis and
  • permanent benzyl/benzylidene acetal protections for hydroxyl groups and application of 9-fluorenylmethoxycarbamate (Fmoc) and azido protecting groups for masking the NH2 functionalities allowed for the stepwise instalment of functional groups (phosphates and fatty acids) into the diglucosamine 44. For the
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Published 04 Jan 2018

Chemical systems, chemical contiguity and the emergence of life

  • Terrence P. Kee and
  • Pierre-Alain Monnard

Beilstein J. Org. Chem. 2017, 13, 1551–1563, doi:10.3762/bjoc.13.155

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  • “processes” that led to the selection. While the selection of fatty acids is undisputed as they are the main constituents of the hydrophobic core of modern membranes, their involvement in forming protocell compartments as the only type of amphiphiles can be disputed. Indeed, other amphiphiles or co
  • catalysis was demonstrated yet, amino acid and peptide-derivatized fatty acids (synthesized via a prebiotically plausible route) have been shown to associate with fatty acid vesicles. Vesicles with arginine-derivatized fatty acids could even electrostatically recruit RNA from the surrounding medium [70
  • ]. Such vesicles with associated ribozymes could eventually prove to be novel functional chemical systems. The production of fatty acids from non-amphiphilic picolylesters performed using a photochemical reaction involving a ruthenium tris(bipyridine), functioning as photosensitizer and redox catalyst
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Published 07 Aug 2017

From chemical metabolism to life: the origin of the genetic coding process

  • Antoine Danchin

Beilstein J. Org. Chem. 2017, 13, 1119–1135, doi:10.3762/bjoc.13.111

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  • , essential for compartmentalisation [29]), a variety of (iso)peptides as in the synthesis of fatty acids today, non-ribosomal peptides and polyketides [30]. The involvement of thioesters in a primitive metabolism, predating the systematic input of phosphate has been documented by Segré and co-workers in a
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Published 12 Jun 2017

Lipids: fatty acids and derivatives, polyketides and isoprenoids

  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2017, 13, 793–794, doi:10.3762/bjoc.13.78

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  • Jeroen S. Dickschat Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Straße 1, D-53121 Bonn, Germany 10.3762/bjoc.13.78 Keywords: fatty acids; isoprenoids; polyketides; Lipids fulfill various functions in life as membrane
  • brain dysfunctions, especially if the sphingolipid metabolism is affected, which can often be related to a specific genetic mutation. Sensu stricto, lipids are defined as apolar natural products that can be classified as fatty acids, whose derivatives are waxes, triacylglycerides, phospholipids
  • fundamentally different biosynthetic origin from fatty acids since they are made via terpene biosynthetic pathways. Nevertheless, steroids are highly apolar yet may contain a polar headgroup such as a 3-hydroxy function (as in lanosterol). Besides membrane formation, the highly apolar character of lipids has
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Published 27 Apr 2017

Polyketide stereocontrol: a study in chemical biology

  • Kira J. Weissman

Beilstein J. Org. Chem. 2017, 13, 348–371, doi:10.3762/bjoc.13.39

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  • biosynthesis, full reduction to the fatty acyl group occurs systematically), and polyketides are most typically released in cyclic form, whereas fatty acids are liberated as carboxylic acids. The much more complicated biosynthetic control in PKSs is achieved by successive action of multiple FAS-like modules
  • stereochemistry can be introduced at several points within the pathways. For example, although fatty acids are constructed primarily from malonyl-CoA units, the AT domains of cis-AT PKSs exhibit specificity towards a number of branched extender units (including methylmalonyl-CoA, ethylmalonyl-CoA, hydroxymalonyl
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Published 24 Feb 2017

Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

  • Naganna Narra,
  • Shiva Shanker Kaki,
  • Rachapudi Badari Narayana Prasad,
  • Sunil Misra,
  • Koude Dhevendar,
  • Venkateshwarlu Kontham and
  • Padmaja V. Korlipara

Beilstein J. Org. Chem. 2017, 13, 26–32, doi:10.3762/bjoc.13.4

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  • phenolics and the lipid involved in one chemical entity [4][5]. Lipids, especially fatty acids and their derivatives are known for their broad spectrum of activity which expands their application in developing new hybrid biomolecules which help in host defenses against potential pathogenic microbes
  • transesterified with different oils or triglycerides [6]. Apart from these structured phenolipids, different fatty acids were esterified with phenolic compounds to produce novel esters which were evaluated for anti-oxidant and antimicrobial activities [7][8]. However, there are very few reports where the phenolic
  • acids have been derivatized with other functionalities apart from esters. The reported compounds other than esters were amides where bioconjugates of fatty acids and amino acids were prepared and evaluated for their anti-oxidant activity by a DPPH radical assay [9]. In view of developing new conjugates
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Published 04 Jan 2017

Synthesis of acylhydrazino-peptomers, a new class of peptidomimetics, by consecutive Ugi and hydrazino-Ugi reactions

  • Angélica de Fátima S. Barreto,
  • Veronica Alves dos Santos and
  • Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2016, 12, 2865–2872, doi:10.3762/bjoc.12.285

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  • aldehydes, ketones and carboxylic acids succeeded in the hydrazino-Ugi reaction, except for paraformaldehyde, fatty acids and aromatic substrates, which led to formation of a complex mixture. These results limited the obtention of a greater variety of acylhydrazino-peptomers by this method. The choice of
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Published 27 Dec 2016

Chemical probes for competitive profiling of the quorum sensing signal synthase PqsD of Pseudomonas aeruginosa

  • Michaela Prothiwa,
  • Dávid Szamosvári,
  • Sandra Glasmacher and
  • Thomas Böttcher

Beilstein J. Org. Chem. 2016, 12, 2784–2792, doi:10.3762/bjoc.12.277

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  • catalyzes the condensation with malonyl-CoA to form 2-aminobenzoylacetyl-CoA. The thioesterase PqsE hydrolyses the thioester to produce 2-aminobenzoylacetate (2-ABA) [13]. The PqsBC complex finally generates HHQ or other AQs in a decarboxylative condensation reaction of 2-ABA with fatty acids loaded on PqsC
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Published 20 Dec 2016

Benzothiadiazole oligoene fatty acids: fluorescent dyes with large Stokes shifts

  • Lukas J. Patalag and
  • Daniel B. Werz

Beilstein J. Org. Chem. 2016, 12, 2739–2747, doi:10.3762/bjoc.12.270

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  • Lukas J. Patalag Daniel B. Werz Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany 10.3762/bjoc.12.270 Abstract Herein, we report on the synthesis and characterization of novel fluorescent fatty acids with large Stokes shifts. Three
  • -dipyrromethene) [11][12], BOIMPY- (bis(borondifluoride)-8-imidazodipyrromethene) [13] and pyrene-labeled fatty acids [14]. Of course, all these alterations might also affect the membrane structure and its dynamics. While the NBD-fluorophore suffers from unsuitable polarity, a pyrene motif disrupts the unpolar
  • membrane core with high bulkiness. BODIPY and BOIMPY scaffolds on the other hand expose fluoride residues which might be able to interact with polarized H–X bonds. Therefore, we synthesized pentaene and hexaene fatty acids which bear five or six double bonds at the terminus or in the middle of the acyl
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Published 14 Dec 2016

Electron-transfer-initiated benzoin- and Stetter-like reactions in packed-bed reactors for process intensification

  • Anna Zaghi,
  • Daniele Ragno,
  • Graziano Di Carmine,
  • Carmela De Risi,
  • Olga Bortolini,
  • Pier Paolo Giovannini,
  • Giancarlo Fantin and
  • Alessandro Massi

Beilstein J. Org. Chem. 2016, 12, 2719–2730, doi:10.3762/bjoc.12.268

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  • reaction setup [22][23][24]. An integrated flow system for the synthesis of biodiesel employing an uninterrupted sequence of two fixed-bed reactors packed with a supported acid for esterification of free fatty acids and with an immobilized imidazolidene catalyst for transesterification has been recently
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Published 13 Dec 2016

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

  • Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

Graphical Abstract
  • view, they can be divided into eight categories: fatty acids (and their derivatives: mono-, di- and triglycerides and phospholipids), acylglycerols, phosphoglycerides, sphingolipids, glycolipids and polyketides, which result from the condensation of ketoacyl groups, sterols (e.g., cholesterol) and
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Published 07 Dec 2016

Selective synthesis of thioethers in the presence of a transition-metal-free solid Lewis acid

  • Federica Santoro,
  • Matteo Mariani,
  • Federica Zaccheria,
  • Rinaldo Psaro and
  • Nicoletta Ravasio

Beilstein J. Org. Chem. 2016, 12, 2627–2635, doi:10.3762/bjoc.12.259

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  • agreement with the acidic character of these materials, often shown by our group. In particular we reported on the relevant activity and robustness of SiZr 4.7 in the esterification of fatty acids with methanol [24] or with polyols [25][26]. However, significant differences were found among the four solids
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Published 06 Dec 2016

The direct oxidative diene cyclization and related reactions in natural product synthesis

  • Juliane Adrian,
  • Leona J. Gross and
  • Christian B. W. Stark

Beilstein J. Org. Chem. 2016, 12, 2104–2123, doi:10.3762/bjoc.12.200

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  • , polyketides, amino acids, fatty acids as well as acetogenins and terpenoids) are summarized in this review article. Putative structures of geraniol 1a (R = H) or 1b (R = H) (in 1924), their expected dihydroxylation products 2a or 2b and the true structure 3 as determined by Klein and Rojahn in 1965 [8
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Published 30 Sep 2016

Ionic liquids as transesterification catalysts: applications for the synthesis of linear and cyclic organic carbonates

  • Maurizio Selva,
  • Alvise Perosa,
  • Sandro Guidi and
  • Lisa Cattelan

Beilstein J. Org. Chem. 2016, 12, 1911–1924, doi:10.3762/bjoc.12.181

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  • noted that for such reactions, acidic IL-based catalysts are preferred over basic ones due to the presence of significant amounts of free fatty acids in the bio-oils used as feedstocks for biodiesel. Li et al. for example designed an innovative combination of imidazolium ILs and metal sulfates acting as
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Published 26 Aug 2016

Rearrangements of organic peroxides and related processes

  • Ivan A. Yaremenko,
  • Vera A. Vil’,
  • Dmitry V. Demchuk and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

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Published 03 Aug 2016

Organic chemistry meets polymers, nanoscience, therapeutics and diagnostics

  • Vincent M. Rotello

Beilstein J. Org. Chem. 2016, 12, 1638–1646, doi:10.3762/bjoc.12.161

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  • used to "pin" arginine-capped nanoparticles to oil droplets comprised of fatty acids. This trick worked remarkably well, providing ~150 nm nanocapsules. These capsules were unstable in serum however. Reaching back to our nanocomposite work, we were able to use bricks and mortar assembly of anionic
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Published 02 Aug 2016

Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides

  • Franziska Hemmerling and
  • Frank Hahn

Beilstein J. Org. Chem. 2016, 12, 1512–1550, doi:10.3762/bjoc.12.148

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  • (3HAD). Enzymes of this family catalyse the dehydration of L-3-hydroxyacyl-CoA during β-oxidation of fatty acids. In this case, it acts as a ketoreductase that installs the secondary hydroxy group in 39. The catalytic mechanism has been proposed using a homologous 3HAD from the human heart as a model
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Published 20 Jul 2016

Muraymycin nucleoside-peptide antibiotics: uridine-derived natural products as lead structures for the development of novel antibacterial agents

  • Daniel Wiegmann,
  • Stefan Koppermann,
  • Marius Wirth,
  • Giuliana Niro,
  • Kristin Leyerer and
  • Christian Ducho

Beilstein J. Org. Chem. 2016, 12, 769–795, doi:10.3762/bjoc.12.77

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  • a semisynthetic approach for modifications of muraymycin C1 as starting point of their SAR studies (Figure 7) [86]. In accordance with the results reported by McDonald et al., their work was based on the assumption that the cellular uptake required for MraY inhibition is mainly dependent on fatty
  • acids connected to the hydroxyleucine moiety. The attachment of lipophilic groups on either the primary or both the primary and secondary amino function was supposed to have similar effects. The muraymycin derivatives 72–86 were thus evaluated against the target in a coupled MraY–MurG in vitro assay
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Published 22 Apr 2016

From steroids to aqueous supramolecular chemistry: an autobiographical career review

  • Bruce C. Gibb

Beilstein J. Org. Chem. 2016, 12, 684–701, doi:10.3762/bjoc.12.69

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  • the guest must adopt a J- or U-shape within the cavity; a motif that is sometimes seen when fatty acids bind to fatty-acid transport proteins. Finally, the third and highest energy guest motif within the capsule can be observed with guests such as C26H54. This guest packs with each methyl terminus in
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Published 12 Apr 2016

Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins

  • Guozheng Huang,
  • Simon Schramm,
  • Jörg Heilmann,
  • David Biedermann,
  • Vladimír Křen and
  • Michael Decker

Beilstein J. Org. Chem. 2016, 12, 662–669, doi:10.3762/bjoc.12.66

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  • (kernels) of H. wightiana, contains besides hydnocarpin mainly cyclopentenoic fatty acids [16], which show pronounced antibiotic activity and inhibit multiplication of mycobacteria [17]. Combination of these antibiotics together with hydnocarpin (MDR inhibitor) helped to treat such a persistent disease
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Published 08 Apr 2016

Biosynthesis of α-pyrones

  • Till F. Schäberle

Beilstein J. Org. Chem. 2016, 12, 571–588, doi:10.3762/bjoc.12.56

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  • following polymerization to fatty acids [34]. Now, it is generally accepted that most α-pyrones are synthesized via the polyketide pathway. Solely for plant-derived ellagitannins another biosynthetic origin was described. Via the shikimate pathway gallic acid is generated, which represents the precursor in
  • biosynthesis: The mechanisms of chain elongation resemble each other, and simple building blocks, e.g., acetyl-CoA and malonyl-CoA, are used to build up the molecule [74]. In general both, polyketides and fatty acids are assembled by repeating Claisen-condensations between an activated acyl-starter unit and
  • -oxohexanoyl thioester and different thioesters of straight-chain and iso-branched chain fatty acids [14]. The mechanism proposal also includes the catalytic cysteine. The first chain, i.e., thioester-activated 9-methyldecanoic acid, gets covalently tethered to that important residue within the active site
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Published 24 Mar 2016

Thermal and oxidative stability of Atlantic salmon oil (Salmo salar L.) and complexation with β-cyclodextrin

  • Daniel I. Hădărugă,
  • Mustafa Ünlüsayin,
  • Alexandra T. Gruia,
  • Cristina Birău (Mitroi),
  • Gerlinde Rusu and
  • Nicoleta G. Hădărugă

Beilstein J. Org. Chem. 2016, 12, 179–191, doi:10.3762/bjoc.12.20

Graphical Abstract
  • first time. The main omega-3 fatty acids, EPA and DHA, were significantly degraded, even at 50 °C. Their relative concentrations decrease from 6.1% for EPA and 4.1% for DHA to 1.7% and 1.5% after degradation at 150 °C, respectively. On the other hand, the relative concentrations of monounsaturated and
  • saturated fatty acids remained constant or slightly increased by a few percent after degradation (e.g., from 10.7% to 12.9% for palmitic acid). Co-crystallization of ASO with β-CD at a host–guest ratio of 1:1 and 3:1 from an ethanol–water mixture and kneading methods has been used for the preparation of β
  • had a total concentration of 25.4% and the main FAMEs were linoleic acid methyl ester (11.2%), EPA methyl ester (6.1%) and DHA methyl ester (4.1%). Myristic, palmitic and stearic acid methyl esters were the most important saturated fatty acids (SFAs) (3.5%, 10.7% and 2.7%, respectively). Some of the
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Published 02 Feb 2016

Synthesis of Xenia diterpenoids and related metabolites isolated from marine organisms

  • Tatjana Huber,
  • Lara Weisheit and
  • Thomas Magauer

Beilstein J. Org. Chem. 2015, 11, 2521–2539, doi:10.3762/bjoc.11.273

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  • cyclononene framework (Figure 3). For example, a class of bicyclic sesquiterpenes, caryophyllenes [21], exhibit the same bicyclo[7.2.0]undecane skeleton as xeniaphyllanes. Furthermore, while monocyclic azamilides [22] are seco-A-ring diterpenoids that are acylated with fatty acids, Dictyota diterpenes [23][24
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Published 10 Dec 2015
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