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Search for "fatty acid" in Full Text gives 113 result(s) in Beilstein Journal of Organic Chemistry.
Recent progress in the synthesis of homotropane alkaloids adaline, euphococcinine and N-methyleuphococcinine
Beilstein J. Org. Chem. 2021, 17, 28–41, doi:10.3762/bjoc.17.4
- this precursor in (−)-adaline, supporting fatty acid origin for this alkaloid. Reflex bleeding is costly due to energy expended in chemical synthesis and fluid loss. Therefore, it is only deployed when other strategies have failed, and the ladybird is in severe danger [35][36]. A massive discrepancy in
Selected peptide-based fluorescent probes for biological applications
Beilstein J. Org. Chem. 2020, 16, 2971–2982, doi:10.3762/bjoc.16.247
- in nature as it contains minimum six fatty acid chains. It is toxic at higher concentration and has been identified in sepsis or septic shock in humans [58]. It induces a strong immune response in normal mammalian cells. Schmuck et al. reported cationic peptide-based polydiacetylene (PDA) liposomes
On the mass spectrometric fragmentations of the bacterial sesterterpenes sestermobaraenes A–C
Beilstein J. Org. Chem. 2020, 16, 2807–2819, doi:10.3762/bjoc.16.231
- reaction proceeds in reverse order of a thermal reaction promoted by the thermal conditions of the gaschromatographic analysis) [14]. The fragmentation reactions of structurally simple compounds such as fatty acid methyl esters have been well investigated by isotopic labelling experiments [15][16] and the
3-Acetoxy-fatty acid isoprenyl esters from androconia of the ithomiine butterfly Ithomia salapia
Beilstein J. Org. Chem. 2020, 16, 2776–2787, doi:10.3762/bjoc.16.228
- (Nymphalidae: Danainae) have hairpencils on the forewings (i.e., androconia) that disseminate semiochemicals during courtship. While most ithomiines are known to contain derivatives of pyrrolizidine alkaloids, dihydropyrrolizines, or γ-lactones in these androconia, here we report on a new class of fatty acid
- species in regions where they co-occur. Furthermore, the occurrence of positional isomers of unsaturated fatty acid derivatives indicates activity of two different desaturases within these butterflies, Δ9 and Δ11, which has not been reported before in male Lepidoptera. Keywords: fatty acid esters; mass
- -6-nonenoic acid and derivatives including dimers and fatty acid conjugates as major constituents of the androconia of Oleria onega [18]. Here we report on the chemical composition of the androconia of Ithomia salapia aquinia and I. s. derasa. A new type of butterfly scent gland constituents
Synthesis of monophosphorylated lipid A precursors using 2-naphthylmethyl ether as a protecting group
Beilstein J. Org. Chem. 2020, 16, 1955–1962, doi:10.3762/bjoc.16.162
- - and 3,3′-O-acylation (Figure 1). The associated fatty acid acyl chains may be conserved within a species but can vary significantly in terms of the chain number and length for lipid A of different bacterial origins [3][4]. Lipid A represents a particularly important subject to research given the
- might harness these immunostimulatory effects are particularly valuable as they can provide basis for the development of vaccines and adjuvants. For example, recent studies have disclosed that both the fatty acid structure and the phosphorylation degree can affect the activity and endotoxic effects [7
- by treatment with triethylamine, and the resulting amine again was immediately acylated with (R)-3-(2-naphthylmethoxy)tetradecanoic acid (7) to afford disaccharide 28 with four fatty acid chains. After cleavage of the anomeric TBS moiety employing HF in pyridine, the resulting anomeric hydroxy group
Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore
Beilstein J. Org. Chem. 2020, 16, 1111–1123, doi:10.3762/bjoc.16.98
- in the last few years due to the discovery that truxillic acid derivatives are inhibitors of FABP (fatty acid binding proteins), which are responsible for the cellular reuptake of anandamide, an endocannabinoid neurotransmitter, and that they can be involved in a very efficient treatment for chronic
Fabclavine diversity in Xenorhabdus bacteria
Beilstein J. Org. Chem. 2020, 16, 956–965, doi:10.3762/bjoc.16.84
- for bioactive compounds are required, such as the bacterial genera Xenorhabdus or Photorhabdus. In these strains, fabclavines are widely distributed SMs with a broad-spectrum bioactivity. Fabclavines are hybrid SMs derived from nonribosomal peptide synthetases (NRPS), polyunsaturated fatty acid (PUFA
- ]. Fabclavines are hexapeptide/polyketide hybrids derived from nonribosomal peptide synthetases (NRPS) and a polyketide synthase (PKS), which are connected to an unusual polyamine derived from polyunsaturated fatty acid (PUFA) synthases [20]. Beside full-length fabclavines, also shortened derivatives were
Two antibacterial and PPARα/γ-agonistic unsaturated keto fatty acids from a coral-associated actinomycete of the genus Micrococcus
Beilstein J. Org. Chem. 2020, 16, 297–304, doi:10.3762/bjoc.16.29
- preference that 1 is more effective to the former strain while 2 is so to the latter. In addition, compounds 1 and 2 displayed agonistic activity against peroxisome proliferator-activated receptors (PPARs) with an isoform specificity towards PPARα and PPARγ. Keywords: antibacterial; coral; keto fatty acid
- ongoing screening program to discover new natural products from coral-associated bacteria, we have recently reported a catecholate siderophore, labrenzbactin, from an alphaproteobacterium Labrenzia [17] and an unsaturated fatty acid with unique methylation pattern from a gammaproteobacterium Microbulbifer
- exhibit pharmaceutically important activity. (9E,11E)-13-Oxooctadecadienoic acid is a PPARα activator found in tomato juice. This keto fatty acid decreases plasma and hepatic triglyceride in obese diabetic mice by activating PPARα transcription [32]. (10E,12E)-9-Oxooctadecadienoic acid isolated from
Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis
Beilstein J. Org. Chem. 2019, 15, 2631–2643, doi:10.3762/bjoc.15.256
- side chains present in the (iso)nanangenines could be derived either from a fatty acid synthase (FAS) or polyketide synthase (PKS). For example, in aflatoxin biosynthesis, the hexanoyl started unit is supplied by a FAS [31], while in the meroterpenoid fumagillin biosynthesis, the unsaturated acyl chain
Current understanding and biotechnological application of the bacterial diterpene synthase CotB2
Beilstein J. Org. Chem. 2019, 15, 2355–2368, doi:10.3762/bjoc.15.228
- hydrolysis of the fatty acid ester bonds of lysophospholipids [31][41]. Moreover, cyclooctatin (5) was shown to be effective against Plasmodium falciparum with an IC50 of 7.14 µg/mL along with very low cytotoxicity [42]. CotB2 belongs to the class of cyclopentane-forming diterpene synthases [46], a class of
Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp.
Beilstein J. Org. Chem. 2019, 15, 2327–2332, doi:10.3762/bjoc.15.225
- analysis revealed that 1 is an unsaturated fatty acid in which a methyl group is located in an uncommon position as a natural product. Feeding experiments of 13C-labeled precursors clarified that ʟ-methionine-derived methylation takes place at the carbon which is derived from the carbonyl carbon of acetate
- . Compound 1 showed weak growth inhibition against Saccharomyces cerevisiae. Keywords: biosynthesis; fatty acid; marine bacteria; methylation; Microbulbifer; Introduction Marine microbial symbionts are currently recognized as a reservoir of new bioactive compounds [1]. The most well-studied host animal is
- corroborated by 3JHH vicinal coupling constant (JH4,H5 = 15.8 Hz). In fungi and certain kinds of bacteria, methyl substituents in the fatty acid carbon chain or the polyketide chain are derived from the methyl group of S-adenosylmethionine (SAM) (Figure 3A) [13][14]. This methylation reaction usually occurs at
Diastereo- and enantioselective preparation of cyclopropanol derivatives
Beilstein J. Org. Chem. 2019, 15, 752–760, doi:10.3762/bjoc.15.71
- transformations [1]. The cyclopropane subunit is also present in many biologically important compounds such as pheromones, fatty acid metabolites, unusual amino acids and possess interesting herbicidal, insecticidal, antibiotic, antibacterial, antifungal, antiviral and antitumor activities [2]. For these reasons
Chemical structure of cichorinotoxin, a cyclic lipodepsipeptide that is produced by Pseudomonas cichorii and causes varnish spots on lettuce
Beilstein J. Org. Chem. 2019, 15, 299–309, doi:10.3762/bjoc.15.27
- structurally distinct from the cichopeptins. The structural differences are as follows: four of the amino acid residues are different, and the lipophilic fatty acid also differs between the two toxins. Moreover, one of 22 amino acids was not definitively identified. Thus, cichopeptins A and B are different
- of the fragment ions in the FABMS spectrum of cichorinotoxin (Figure 1) showed the presence of the following peptide segment: Pro-Ala-Ala-Ala-Val-Ala-dhThr-Ala-Val (Figure 2). As described below, this toxin has a 3-hydroxydecanoic acid moiety as a fatty acid. Furthermore, the amino group at the N
- this fatty acid moiety, cichorinotoxin (2.0 mg) was hydrolyzed at 120 °C for 90 min with 1.0 mL of 6 N aqueous HCl. EtOAc (1.5 mL) was added to the hydrolysate, and then the fatty acid was extracted. The extract was dried over anhydrous MgSO4 and concentrated in vacuo. A mixture (1.0 mL) of
An overview on recent advances in the synthesis of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials and their catalytic applications in chemical processes
Beilstein J. Org. Chem. 2018, 14, 2745–2770, doi:10.3762/bjoc.14.253
- , triazolo[1,2-a]indazoletrione derivatives, tetrasubstituted imidazole derivatives, aromatic/aliphatic sulfide derivatives, and N-substituted pyrrole derivatives. These catalysts were used in cellulose hydrolysis, cellobiose hydrolysis, production of fatty acid ethyl ester, the transesterification of
- triglycerides with methanol, the etherification of isopentene with methanol, the esterification of palm fatty acid distillate with methanol, the dehydration of D-xylose into furfural, the production of ethyl acetate from ethanol and acetic acid, and the transesterification of palm oil with methanol into biodiesel
- the next example, sulfonated multi-walled carbon nanotubes were reported as a catalyst to produce fatty acid ethyl ester (biodiesel production). In this case, triglycerides 108 and ethanol were absorbed through the interaction between the acid sites on MWCNTs and the oxygen atom of substrates. The
Targeting the Pseudomonas quinolone signal quorum sensing system for the discovery of novel anti-infective pathoblockers
Beilstein J. Org. Chem. 2018, 14, 2627–2645, doi:10.3762/bjoc.14.241
- -CoA) is then transferred to an active-site cysteine of the β-ketoacyl-ACP synthase III (FabH)-type enzyme PqsD [26][27]. Subsequently, another CoA-activated substrate comes into play. In analogy to fatty acid synthesis, malonyl-CoA is reacted with the enzyme-bound thioester to yield 2
- formed by action of the heterodimeric complex PqsBC. This time, CoA-activated octanoic acid is used to preload an active-site cysteine of PqsC with the fatty acid via a thioester linkage [30][31]. The previously produced 2-ABA is then consumed to from HHQ under decarboxylative condensation [30]. Finally
Comparative cell biological study of in vitro antitumor and antimetastatic activity on melanoma cells of GnRH-III-containing conjugates modified with short-chain fatty acids
Beilstein J. Org. Chem. 2018, 14, 2495–2509, doi:10.3762/bjoc.14.226
- most potent one in all different assays (enzymatic stability, cellular uptake, and in vitro antitumor activity) on HT-29 colon carcinoma cell lines [19]. The different hydrophobicity of conjugates having a short, fatty acid side chain (2–6 carbon atoms) could be excluded as an explanation for their
- , cellular uptake and weaker antitumor activity [17][19]. The increased cytostatic activity of Dau–GnRH-III conjugates acylated by a short-chain fatty acid as a “second drug” can be due to the known potential of short-chain fatty acids – especially butyric acid – to induce apoptosis in various tumor cell
- development. Conclusion In the present study, GnRH-III or its analog substituted with a short-chain fatty acid containing Lys in position 4 was applied as a targeting unit to deliver Dau to melanoma cells. By reading their complex cell physiological activities these conjugates, in which Dau was linked via an
Acyl-group specificity of AHL synthases involved in quorum-sensing in Roseobacter group bacteria
Beilstein J. Org. Chem. 2018, 14, 1309–1316, doi:10.3762/bjoc.14.112
- Phaeobacter inhibens strains, revealing strain-specific mixtures. Although large differences were present between the species, the fatty acid profiles, the pool for the acyl precursors for AHL biosynthesis, were very similar. To test the acyl-chain selectivity, the three enzymes LuxI1 and LuxI2 from D. shibae
- ; fatty acid composition; N-acylhomoserine lactones; quorum sensing; Phaeobacter inhibens; Introduction The Roseobacter group, a subgroup of the Rhodobacteraceae family, constitutes an important class of Gram-negative marine bacteria, occurring in many different habitats [1][2], in fresh water as well as
- . gallaeciensis BS107 produced eight different AHLs [8]. The biosynthesis of AHLs is mediated by the enzyme LuxI or its homologs, and often accompanied by a regulator protein, LuxR [18][19]. An ACP-bound fatty acid acyl group 1 is transferred onto the amino group of S-adenosylmethionine (SAM, 2) that is followed
Volatiles from three genome sequenced fungi from the genus Aspergillus
Beilstein J. Org. Chem. 2018, 14, 900–910, doi:10.3762/bjoc.14.77
- encoded terpene synthases for each strain. Besides terpenes, a series of aromatic compounds and volatiles derived from fatty acid and branched amino acid metabolism were identified. Some of these compounds have not been described as fungal metabolites before. For the compound ethyl (E)-hept-4-enoate known
- unusual, because many ethyl esters and esters derived from carboxylic acids with an odd number of carbons were found. Since the carboxylic acid portion usually derives from fatty acid biosynthesis, a process in which the C2 starter acetyl-CoA is elongated with C2 units, esters from carboxylic acids with
Volatiles from the tropical ascomycete Daldinia clavata (Hypoxylaceae, Xylariales)
Beilstein J. Org. Chem. 2018, 14, 135–147, doi:10.3762/bjoc.14.9
- different compound classes including fatty acid derivatives and polyketides, aromatic compounds, terpenes, sulfur and nitrogen compounds, and halogenated compounds is produced by ascomycete fungi [1]. Possibly the most widespread volatile secondary metabolite from fungi is (R)-oct-1-en-3-ol (1, Scheme 1), a
Aminosugar-based immunomodulator lipid A: synthetic approaches
Beilstein J. Org. Chem. 2018, 14, 25–53, doi:10.3762/bjoc.14.3
- the azido function with zinc in acetic acid followed by acylation of the liberated amino group with the long-chain acyloxyacyl fatty acid furnished fully acylated 16. In the next steps, the isopropylidene acetal and anomeric TDS ether were removed by treatment with aqueous TFA and the anomeric
- in AcOH which reductively cleaved the N-Troc group (Scheme 3). After N-acylation by (R)-3 acyloxyacyl fatty acid and hydrolytic cleavage of 4’,6’-O-benzylidene acetal group with 90% aqueous TFA, the liberated 6’-hydroxy group was regioselectively protected as TBDMS ether to furnish 20. 1H-Tetrazole
- the corresponding fatty acid using 2-methyl-6-nitrobenzoic anhydride (MNBA) as activating reagent in the presence of the nucleophilic catalysts 4-(dimethylamino)pyridine N-oxide (DMAPO) [89]. Next, the 2-N-Alloc group was cleaved by treatment with Pd(PPh3)4 and dimethylaminotrimethylsilane (TMSDMA
The chemistry and biology of mycolactones
Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159
- of the mycolactone core Currently, all mycolactone partial and total syntheses share the (projected) final esterification of the C5-hydroxy group of the appropriately protected extended mycolactone core with the respective polyunsaturated fatty acid under Yamaguchi conditions (Figure 7). Two
Chemical systems, chemical contiguity and the emergence of life
Beilstein J. Org. Chem. 2017, 13, 1551–1563, doi:10.3762/bjoc.13.155
- chemicals with fatty acid vesicles demonstrates that chemical systems, even simple ones, could have spawned such a selection by conditioning the interactions between their molecular constituents. For instance, canonical nucleobases interact more extensively with the vesicles structures than some of their
- derivatives and even stabilize them [63]. The same observation was made for ribose over other sugars. Moreover, when the permeability of fatty acid vesicle bilayers towards sugars was examined, ribose was determined to have the highest diffusion rates among aldopentoses or hexoses [64], a fact that could also
- authors surmised that the product length (up 29 monomer units compared to 9 in aqueous set-ups) was possible due to solubilization of the products within the hydrophobic core of the vesicle bilayers. Recent investigations with potentially prebiotic fatty acid structures have confirmed these observations
A new member of the fusaricidin family – structure elucidation and synthesis of fusaricidin E
Beilstein J. Org. Chem. 2017, 13, 1430–1438, doi:10.3762/bjoc.13.140
- most likely shows similarity to the fatty acid synthesis pathway [2]. All fusaricidins have three amino acids (L-Thr, D-allo-Thr, and D-Ala) in common and are mostly isolated in pairs which differ in a single amino acid (asparagine vs glutamine). There are several known members of the fusaricidin
- bound to a guanidine β-hydroxy fatty acid as a key correlation was observed between the signal of its α-methine proton at δ 4.46 and the resonance of a carbonyl at δ 171.9. This carbonyl showed HMBC correlation with α-methylene protons at δ 2.35 and the β-methine proton at δ 3.77. Additionally
Framing major prebiotic transitions as stages of protocell development: three challenges for origins-of-life research
Beilstein J. Org. Chem. 2017, 13, 1388–1395, doi:10.3762/bjoc.13.135
- functional capacities (see [15] for a review). In particular, fatty acid vesicles have become the standard protocell model, not just because of their prebiotic plausibility [27][28], but also because of their remarkable stability as compartments [29][30]; their rapid self-assembly kinetics and amenability to
- process of protocell division, as well as developing mechanisms of heredity (i.e., control of trans-generational variation) [60][64]. A possible – though still tentative – narrative would proceed as follows: initially, (Figure 1a) fatty acid vesicles could self-maintain and grow through the acquisition of
- . Protocells as the main units of prebiotic evolution: three hypothetical stages of development toward LUCA, with the correlation between protocell organisation and evolutionary potential depicted at each stage. Adapted from [43]. (a) Self-assembled (poly-disperse and likely multilamellar) fatty acid vesicles
Biomimetic molecular design tools that learn, evolve, and adapt
Beilstein J. Org. Chem. 2017, 13, 1288–1302, doi:10.3762/bjoc.13.125
- the sterol and fatty acid biosynthetic pathways were activated in the MSCs, and subsequent experiments validated the model predictions of increased levels of proteins in these pathways and the formation of lipid rafts on the cell membranes. In silico sparse feature selection thus revealed a hitherto
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