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Journal articles on the topic 'Synthesis of iron acyl'

Author: Grafiati

Published: 4 June 2021

Last updated: 7 February 2022

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1

Liu, Jin-Biao, Miaofeng Ren, Xiaojing Lai, and Guanyinsheng Qiu. "Iron-catalyzed stereoselective haloamidation of amide-tethered alkynes." Chemical Communications 57, no. 35 (2021): 4259–62. http://dx.doi.org/10.1039/d1cc00870f.

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In this work, by using N-methoxybenzamides as efficient acyl nitrene precursors, an iron-catalyzed acyl nitrene/alkyne metalation-based chloramidation is reported for the synthesis of isoindol-5-ones.

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2

Lai, Xiaojing, Jin-Biao Liu, Yu-Chao Wang, and Guanyinsheng Qiu. "Iron-catalyzed intramolecular acyl nitrene/alkyne metalation for the synthesis of pyrrolo[2,1-a]isoindol-5-ones." Chemical Communications 57, no. 16 (2021): 2077–80. http://dx.doi.org/10.1039/d0cc08039j.

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3

Zhao, Da-Wei, Xia-Li Liu, Xiao-Yan Zhang, and Liang-Fu Tang. "Synthesis of acyl iron complexes based on bis(heteroaryl)methanes." Journal of Organometallic Chemistry 780 (March 2015): 56–62. http://dx.doi.org/10.1016/j.jorganchem.2014.12.039.

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4

Zhao, Da-Wei, Yi Xu, Yao-Wei Guo, Hai-Bin Song, and Liang-Fu Tang. "Synthesis and reactivity of (pyrazol-1-yl)acyl iron complexes." Journal of Organometallic Chemistry 791 (August 2015): 303–10. http://dx.doi.org/10.1016/j.jorganchem.2015.06.008.

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5

Xiao, Fuhong, Chao Liu, Dahan Wang, Huawen Huang, and Guo-Jun Deng. "Concise synthesis of ketoallyl sulfones through an iron-catalyzed sequential four-component assembly." Green Chemistry 20, no. 5 (2018): 973–77. http://dx.doi.org/10.1039/c7gc03719h.

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A three starting material four component reaction (3SM-4CR) strategy is described to prepare β-acyl allylic sulfones from methyl ketones, sodium sulfinates and dimethylacetamide (DMA) in an iron-catalyzed oxidative system.

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6

Yang, Tonghao, Yajun Lin, Chaoqun Yang, and Wei Yu. "Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds." Green Chemistry 21, no. 22 (2019): 6097–102. http://dx.doi.org/10.1039/c9gc02085c.

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7

Bisz, Elwira, and Michal Szostak. "Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling of Aryl Chlorobenzoates with Alkyl Grignard Reagents." Molecules 25, no. 1 (January 6, 2020): 230. http://dx.doi.org/10.3390/molecules25010230.

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Aryl benzoates are compounds of high importance in organic synthesis. Herein, we report the iron-catalyzed C(sp2)–C(sp3) Kumada cross-coupling of aryl chlorobenzoates with alkyl Grignard reagents. The method is characterized by the use of environmentally benign and sustainable iron salts for cross-coupling in the catalytic system, employing benign urea ligands in the place of reprotoxic NMP (NMP = N-methyl-2-pyrrolidone). It is notable that high selectivity for the cross-coupling is achieved in the presence of hydrolytically-labile and prone to nucleophilic addition phenolic ester C(acyl)–O bonds. The reaction provides access to alkyl-functionalized aryl benzoates. The examination of various O-coordinating ligands demonstrates the high activity of urea ligands in promoting the cross-coupling versus nucleophilic addition to the ester C(acyl)–O bond. The method showcases the functional group tolerance of iron-catalyzed Kumada cross-couplings.

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8

Thomas, Susan E., Gary J. Tustin, and Arthur Ibbotson. "Synthesis and reactivity of iron carbonyl complexes of α,β-unsaturated acyl silanes." Tetrahedron 48, no. 36 (September 1992): 7629–40. http://dx.doi.org/10.1016/s0040-4020(01)90375-8.

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9

Rück-Braun, Karola, and Jörg Kühn. "Synthesis of Novel Alkynyl-substituted Iron Acyl and Carbene Complexes via Mixed Anhydrides." Synlett 1995, no. 11 (November 1995): 1194–96. http://dx.doi.org/10.1055/s-1995-5204.

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10

Chen, Dafa, Rosario Scopelliti, and Xile Hu. "Synthesis and Reactivity of Iron Acyl Complexes Modeling the Active Site of [Fe]-Hydrogenase." Journal of the American Chemical Society 132, no. 3 (January 27, 2010): 928–29. http://dx.doi.org/10.1021/ja9100485.

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11

Ge, Liang, Yajun Li, and Hongli Bao. "Iron-Catalyzed Radical Acyl-Azidation of Alkenes with Aldehydes: Synthesis of Unsymmetrical β-Azido Ketones." Organic Letters 21, no. 1 (December 24, 2018): 256–60. http://dx.doi.org/10.1021/acs.orglett.8b03688.

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12

Ehlenz, Richard, Martin Nieger, Karri Airola, and Karl Heinz Dötza. "Sugar Acyl Iron Complexes: Synthesis and Conformational Studies in Solution and in the Solid State." Journal of Carbohydrate Chemistry 16, no. 9 (December 1, 1997): 1305–18. http://dx.doi.org/10.1080/07328309708005751.

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13

RUECK-BRAUN, K., and J. KUEHN. "ChemInform Abstract: Synthesis of Novel Alkynyl-Substituted Iron Acyl and Carbene Complexes via Mixed Anhydrides." ChemInform 27, no. 16 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199616207.

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14

THOMAS, S. E., G. J. TUSTIN, and A. IBBOTSON. "ChemInform Abstract: Synthesis and Reactivity of Iron Carbonyl Complexes of α,β- Unsaturated Acyl Silanes." ChemInform 24, no. 1 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199301232.

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15

Bian, Qilong, Cunluo Wu, Jiangpei Yuan, Zuodong Shi, Tao Ding, Yongwei Huang, Hao Xu, and Yuanqing Xu. "Iron Nitrate-Mediated Selective Synthesis of 3-Acyl-1,2,4-oxadiazoles from Alkynes and Nitriles: The Dual Roles of Iron Nitrate." Journal of Organic Chemistry 85, no. 6 (January 29, 2020): 4058–66. http://dx.doi.org/10.1021/acs.joc.9b03070.

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16

Filho, Juvenal C. S., Antonio G. Ferreira, Maria Carolina A. F. Gotardo, and Marilda das Dores Assis. "Mono-crowned substituded iron porphyrin: synthesis, analytical properties and catalytic activity." Journal of Porphyrins and Phthalocyanines 09, no. 09 (September 2005): 637–45. http://dx.doi.org/10.1142/s1088424605000745.

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A substituted porphyrin bearing a crown ether unit, H 2( M 18 C 6 P ), was synthesized from the reaction between (5-mono(o-aminophenyl)10,15,20-triphenylporphyrin) and the acyl derivative of the ether (4-carboxy-18-crown-6). The corresponding iron porphyrin, Fe ( M 18 C 6 P ) Cl , was obtained through iron insertion into H 2( M 18 C 6 P ). The new free-base porphyrin was analyzed by C , N , and H elemental analysis, UV-vis and IR spectroscopies, electrospray mass spectrometry (MS) and 1 H NMR. It selectively extracts 18% of the K + ions present in aqueous medium to the organic phase (chloroform). UV-vis spectroscopy studies showed that H 2( M 18 C 6 P ) is also capable of forming aggregates with K +, probably the 1:1 complex, in methanol. This happens because the ionic radius of the potassium ion is appropriate for its accommodation inside the cavity of the crown ether, and also because of the associative effect between the porphyrin and the crown ether unit. The iron porphyrin Fe ( M 18 C 6 P ) Cl was used as catalyst for the epoxidation of cyclooctene by iodosylbenzene or sodium hypochlorite, in methanol or biphasic water/dichloroethane system, respectively. The results obtained with sodium hypochlorite show that Fe ( M 18 C 6 P ) Cl is a potential catalyst for selective oxidations, because the crown ether unit can select or orient substrates. This iron porphyrin can also be employed as a catalyst in a biphasic water/organic solvent system, with no need of a phase transfer agent.

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17

Cho, Inha, Zhi-Jun Jia, and Frances H. Arnold. "Site-selective enzymatic C‒H amidation for synthesis of diverse lactams." Science 364, no. 6440 (May 9, 2019): 575–78. http://dx.doi.org/10.1126/science.aaw9068.

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A major challenge in carbon‒hydrogen (C‒H) bond functionalization is to have the catalyst control precisely where a reaction takes place. In this study, we report engineered cytochrome P450 enzymes that perform unprecedented enantioselective C‒H amidation reactions and control the site selectivity to divergently construct β-, γ-, and δ-lactams, completely overruling the inherent reactivities of the C‒H bonds. The enzymes, expressed in Escherichia coli cells, accomplish this abiological carbon‒nitrogen bond formation via reactive iron-bound carbonyl nitrenes generated from nature-inspired acyl-protected hydroxamate precursors. This transformation is exceptionally efficient (up to 1,020,000 total turnovers) and selective (up to 25:1 regioselectivity and 97%, please refer to compound 2v enantiomeric excess), and can be performed easily on preparative scale.

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18

Gein, Vladimir L., and Evgenia V. Pastukhova. "Synthesis of 5-aryl-4-acyl-3-hydroxy- 1-carboxymethyl-3-pyrrolin-2-ones." Butlerov Communications 64, no. 11 (November 30, 2020): 9–12. http://dx.doi.org/10.37952/roi-jbc-01/20-64-11-9.

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5-Aryl-1,4-disubstituted terahydropyrrole-2,3-diones are five-membered nitrogen heterocycles containing in the first alkyl position or an aryl functionalized substituent and in the fourth position in another state of nature an acyl residue. Trahydropyrrole-2,3-diones constitute a significant class of available and stable substances. Along with this, they easily enter into reactions with various nucleophilic reagents due to the highly reactive carbonyl group in the third position of the heterocycle. The presence of the latter, as well as the carbonyl group of the side chain, makes it possible to form various condensed systems from heterocycles in reactions with binucleophilic reagents. The synthesis of biologically active substances based on 1,4,5-trisubstituted tetrahydropyrrole-2,3-diones is one of the promising ways of using this class of compounds. Previously, it was found that 1,4,5-trisubstituted 3-hydroxy-3-pyrin-2-ones have anti-inflammatory, analgesic, antimicrobial, nootropic, antiplatelet and antiviral activity. We set the task to obtain 5-aryl-4-acyl-3-hydroxy-3-pyrrolin-2-ones, in the first position of the heterocycle there is a carboxymethyl substituent. By setting up a three-component reaction of acylpyruvic acid ether with aromatic aldehydes and glycine in dioxane in dioxane. The structure of the compound was established on the basis of IR and 1H NMR spectroscopy data. Based on the data of 1H NMR spectroscopy and a positive reaction with an alcoholic solution of iron(III) chloride, the predominant presence of compounds in the enol form was established. The article presents the proposed mechanism and schemes of the formula for the synthesis of 5-aryl-4-acyl-3-hydroxy-1-carboxymethyl-3-pyrrolin-2-ones, their physicochemical and spectral characteristics, as well as the yields of the reaction products.

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19

Hungate, R. W., F. Miller, and M. S. Goodman. "Convenient synthesis of optically active iron acyls." Tetrahedron Letters 29, no. 34 (January 1988): 4273–76. http://dx.doi.org/10.1016/s0040-4039(00)80472-4.

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20

Qin, Suni, Chao Zu, Zilu Chen, Wanyun Huang, Jiangke Qin, and Fupei Liang. "Synthesis, crystal structure and magnetic property of an iron(III) coordination polymer with N-acyl-salicylhydrazide ligand." Inorganic Chemistry Communications 14, no. 6 (June 2011): 1036–38. http://dx.doi.org/10.1016/j.inoche.2011.03.066.

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21

Karamanoli, Katerina, and Steven E. Lindow. "Disruption of N-Αcyl Homoserine Lactone-Mediated Cell Signaling and Iron Acquisition in Epiphytic Bacteria by Leaf Surface Compounds." Applied and Environmental Microbiology 72, no. 12 (September 22, 2006): 7678–86. http://dx.doi.org/10.1128/aem.01260-06.

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ABSTRACT Since N-acyl homoserine lactones (AHLs) are key mediators of cell density-dependent regulation of traits involved in virulence and epiphytic fitness in gram-negative bacteria such as Pseudomonas syringae, a variety of plant species were examined to determine their production of leaf surface compounds that could interact with these signaling systems. Leaf washings of 17 of 52 plant species tested stimulated or inhibited AHL-dependent traits in at least one of the bacterial reporter strains used. The active compounds from most plants could be distinguished from known AHLs due to different patterns of mobility during C8 and C18 reverse-phase thin-layer chromatography (TLC) and normal-phase TLC compared to the patterns for authentic bacterial AHLs. All plant extracts were also tested to determine their abilities to sequester iron and trigger bacterial siderophore synthesis on a medium containing abundant iron. Leaf washings from 16 of the 52 plant species, as well as tannic acid solutions, stimulated pyoverdine synthesis in P. syringae in a high-iron medium. These preparations also inhibited the growth of a P. syringae mutant unable to produce pyoverdine siderophores but not the growth of the wild-type bacterium. The stimulation of siderophore production and the growth inhibition by plant extracts and purified tannins were both reversed by addition of ferric chloride to culture media, indicating that iron was made unavailable by the compounds released onto the leaf surface.

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22

Kidman, Clinton J., Cyril D. S. Mamotte, M. Adrien Eynaud, Juliane Reinhardt, Jitraporn Vongsvivut, Mark J. Tobin, Mark J. Hackett, and Ross M. Graham. "Tracking biochemical changes induced by iron loading in AML12 cells with synchrotron live cell, time-lapse infrared microscopy." Biochemical Journal 478, no. 6 (March 19, 2021): 1227–39. http://dx.doi.org/10.1042/bcj20200653.

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Hepatocytes are essential for maintaining the homeostasis of iron and lipid metabolism in mammals. Dysregulation of either iron or lipids has been linked with serious health consequences, including non-alcoholic fatty liver disease (NAFLD). Considered the hepatic manifestation of metabolic syndrome, NAFLD is characterised by dysregulated lipid metabolism leading to a lipid storage phenotype. Mild to moderate increases in hepatic iron have been observed in ∼30% of individuals with NAFLD; however, direct observation of the mechanism behind this increase has remained elusive. To address this issue, we sought to determine the metabolic consequences of iron loading on cellular metabolism using live cell, time-lapse Fourier transform infrared (FTIR) microscopy utilising a synchrotron radiation source to track biochemical changes. The use of synchrotron FTIR is non-destructive and label-free, and allowed observation of spatially resolved, sub-cellular biochemical changes over a period of 8 h. Using this approach, we have demonstrated that iron loading in AML12 cells induced perturbation of lipid metabolism congruent with steatosis development. Iron-loaded cells had approximately three times higher relative ester carbonyl concentration compared with controls, indicating an accumulation of triglycerides. The methylene/methyl ratio qualitatively suggests the acyl chain length of fatty acids in iron-loaded cells increased over the 8 h period of monitoring compared with a reduction observed in the control cells. Our findings provide direct evidence that mild to moderate iron loading in hepatocytes drives de novo lipid synthesis, consistent with a role for iron in the initial hepatic lipid accumulation that leads to the development of hepatic steatosis.

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23

LaMarca, B. Babbette D., Wenming Zhu, Jean E. L. Arceneaux, B. Rowe Byers, and Michael D. Lundrigan. "Participation of fad and mbt Genes in Synthesis of Mycobactin in Mycobacterium smegmatis." Journal of Bacteriology 186, no. 2 (January 15, 2004): 374–82. http://dx.doi.org/10.1128/jb.186.2.374-382.2004.

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ABSTRACT Colonies of Mycobacterium smegmatis LR222 on iron-limiting (0.1 μM Fe) minimal medium agar fluoresce under UV light due to the accumulation in the cells of the deferri form of the siderophore mycobactin. Two mutants with little or no fluorescence, designated LUN8 and LUN9, were isolated by screening colonies of transposon (Tn611)-mutagenized M. smegmatis. Ferrimycobactin prepared from iron-restricted cells of the wild type had an R f of 0.62 on high-performance thin-layer chromatography (HPTLC) and a characteristic visible absorption spectrum with a peak near 450 nm. Similar extracts from LUN8 cells contained a small amount of ferrimycobactin with an R f of 0.58 on HPTLC and an absorption spectrum with the peak shifted to a wavelength lower than that of the wild-type ferrimycobactin. Nuclear magnetic resonance spectroscopy studies suggested that the LUN8 mycobactin may have an altered fatty acid side chain. Mutant strain LUN9 produced no detectable mycobactin. Neither mutant strain produced measurable amounts of excreted mycobactin, although both excreted exochelin (the mycobacterial peptido-hydroxamate siderophore), and both mutants were more sensitive than the wild-type strain to growth inhibition by the iron chelator ethylenediamine-di(o-hydroxyphenylacetic acid). The transposon insertion sites were identified, and sequence analyses of the cloned flanking chromosome regions showed that the mutated gene in LUN9 was an orthologue of the Mycobacterium tuberculosis mycobactin biosynthetic gene mbtE. The mutated gene in LUN8 had homology with M. tuberculosis fadD33 (Rv1345), a gene that may encode an acyl-coenzyme A synthase and which previously was not known to participate in synthesis of mycobactin.

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24

Courtois, F., I. Suc, C. Garofalo, M. Ledoux, E. Seidman, and E. Levy. "Iron-ascorbate alters the efficiency of Caco-2 cells to assemble and secrete lipoproteins." American Journal of Physiology-Gastrointestinal and Liver Physiology 279, no. 1 (July 1, 2000): G12—G19. http://dx.doi.org/10.1152/ajpgi.2000.279.1.g12.

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Although oxidative stress has been implicated in development of gut pathologies, its role in intestinal fat transport has not been investigated. We assessed the effect of Fe2+-ascorbate-mediated lipid peroxidation on lipid synthesis, apolipoprotein biogenesis, and lipoprotein assembly and secretion. Incubation of postconfluent Caco-2 cells with iron(II)-ascorbate (0.2 mM/2 mM) in the apical compartment significantly promoted malondialdehyde formation without affecting sucrase activity, transepithelial resistance, DNA and protein content, and cell viability. However, addition of the oxygen radical-generating system reduced 1) [14C]oleic acid incorporation into cellular triglycerides (15%, P < 0.0002) and phospholipids (16%, P < 0.0005); 2) de novo synthesis of cellular apolipoprotein A-I (apo A-I) (18%, P < 0.05), apo A-IV (38%, P < 0.05), and apo B-48 (45%, P< 0.003) after [35S]methionine addition; and 3) production of chylomicrons (50%), VLDL (40%), LDL (37%), and HDL (30%) (all P < 0.0001). In contrast, increased total cellular cholesterol formation (96%, P < 0.0001), assayed by [14C]acetate incorporation, was noted, attributable to marked elevation (70%, P < 0.04) in activity of dl-3-hydroxy-3-methyl-glutaryl-CoA reductase, the rate-limiting enzyme in cholesterol synthesis. The ratio of Acyl-CoA to cholesterol acyltransferase, the esterifying cholesterol enzyme, remained unchanged. Fe2+-ascorbate-mediated lipid peroxidation modifies intracellular fat absorption and may decrease enterocyte efficiency in assembling and transporting lipids during gut inflammation.

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25

Sharma, Rakesh K., Manavi Yadav, Rashmi Gaur, Radhika Gupta, Alok Adholeya, and Manoj B. Gawande. "Synthesis of Iron Oxide Palladium Nanoparticles and Their Catalytic Applications for Direct Coupling of Acyl Chlorides with Alkynes." ChemPlusChem 81, no. 12 (September 30, 2016): 1312–19. http://dx.doi.org/10.1002/cplu.201600321.

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26

Taguchi, Fumiko, Yujiro Ogawa, Kasumi Takeuchi, Tomoko Suzuki, Kazuhiro Toyoda, Tomonori Shiraishi, and Yuki Ichinose. "A Homologue of the 3-Oxoacyl-(Acyl Carrier Protein) Synthase III Gene Located in the Glycosylation Island of Pseudomonas syringae pv. tabaci Regulates Virulence Factors via N-Acyl Homoserine Lactone and Fatty Acid Synthesis." Journal of Bacteriology 188, no. 24 (October 6, 2006): 8376–84. http://dx.doi.org/10.1128/jb.00763-06.

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ABSTRACT Pseudomonas syringae pv. tabaci 6605 possesses a genetic region involved in flagellin glycosylation. This region is composed of three open reading frames: orf1, orf2, and orf3. Our previous study revealed that orf1 and orf2 encode glycosyltransferases; on the other hand, orf3 has no role in posttranslational modification of flagellin. Although the function of Orf3 remained unclear, an orf3 deletion mutant (Δorf3 mutant) had reduced virulence on tobacco plants. Orf3 shows significant homology to a 3-oxoacyl-(acyl carrier protein) synthase III in the fatty acid elongation cycle. The Δorf3 mutant had a significantly reduced ability to form acyl homoserine lactones (AHLs), which are quorum-sensing molecules, suggesting that Orf3 is required for AHL synthesis. In comparison with the wild-type strain, swarming motility, biosurfactant production, and tolerance to H2O2 and antibiotics were enhanced in the Δorf3 mutant. A scanning electron micrograph of inoculated bacteria on the tobacco leaf surface revealed that there is little extracellular polymeric substance matrix surrounding the cells in the Δorf3 mutant. The phenotypes of the Δorf3 mutant and an AHL synthesis (ΔpsyI) mutant were similar, although the mutant-specific characteristics were more extreme in the Δorf3 mutant. The swarming motility of the Δorf3 mutant was greater than that of the ΔpsyI mutant. This was attributed to the synergistic effects of the overproduction of biosurfactants and/or alternative fatty acid metabolism in the Δorf3 mutant. Furthermore, the amounts of iron and biosurfactant seem to be involved in biofilm development under quorum-sensing regulation in P. syringae pv. tabaci 6605.

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27

Gein, Vladimir L., and Evgenia V. Pastukhova. "Synthesis and properties of 1-aminocarbonylmethyl-5-aryl- 4-aroyl-3-hydroxy-3-pyrroline-2-ones." Butlerov Communications 64, no. 10 (October 31, 2020): 28–32. http://dx.doi.org/10.37952/roi-jbc-01/20-64-10-28.

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3-Hydroxy-3-pyrrolin-2-ones are fully hydrogenated heterocyclic compounds, the base of which is included in a number of biologically active substances and drugs. Scientists' interest in 3-Hydroxy-3-pyrrolin-2-ones is due to the fact that, with their availability and high stability, they also have high reactivity due to the active carbonyl group in the third position of the heterocycle and easily interact with moconucleophiles. In addition, the presence of acyl and ethoxycarbonyl groups in the fourth position of the heterocycle makes it possible to obtain various condensed systems in reactions with binucleophiles, thereby making it possible to expand the range of the indicated compounds. We set the task to prepare 5-aryl-4-acyl-3-hydroxy-3-pyrrolin-2-ones containing an amino-carbonylmethyl substituent in the first position of the heterocycle, which were not previously described in the literature. It was also supposed to establish how the obtained compounds react with hydrazine hydrate. A series of 1-aminocarbonylmethyl-5-aryl-4-aroyl-3-hydroxy-3-pyrrolin-2-ones was obtained by setting up a three-component reaction of aroylpyruvic acid methyl ester with aromatic aldehydes and glycinamide hydrochloride in glacial acetic acid. The structure of the obtained compounds was established on the basis of IR and 1H NMR spectroscopy data. Based on the data of 1H NMR spectroscopy and a positive reaction with an alcoholic solution of iron(III) chloride, the predominant existence of the obtained compounds in the enol form was established. The article describes the mechanism of three-component reactions, the structural formulas of the obtained compounds, their physicochemical properties and spectral characteristics, as well as the yields of the reaction products. We have also studied the interaction of 1-substituted 5-aryl-4-acyl-3-hydroxy-3-pyrrolin- 2-ones with such a binucleophilic reagent as hydrazine hydrate. As a result of refluxing 1-amino-carbonylmethyl-3-hydroxy-4-(4-methoxybenzoyl)-5-(2-chlorophenyl)-3-pyrrolin-2-one and hydrazine hydrate in glacial acetic acid, 2-[4-(2-chlorophenyl)-3-(4-methoxyphenyl)-6-oxo-4,6-dihydropyrrolo [3,4-c] pyrazol-5(1H)-yl] acetamide. The article describes the proposed reaction mechanism, product yield, its physicochemical properties and spectral characteristics.

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28

Okafor, Emmanuel C., Nsukka Nigeria, and Bieluonwu A. Uzoukwu. "Iron(III) Complexes of 4-Acyl Derivatives of 1-Phenyl-3-Methyl—Pyrazolone-5: Synthesis, Magnetic and Spectroscopic Studies." Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry 22, no. 7 (July 1992): 921–27. http://dx.doi.org/10.1080/15533179208016601.

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29

Wang, Lei, Kai Ren, Min Wang, and Ping Liu. "Iron-Catalyzed Synthesis of Selenoesters from Diselenides and Acyl Chlorides or Acid Anhydrides in the Presence of Magnesium Dust." Synthesis 2010, no. 07 (January 20, 2010): 1078–82. http://dx.doi.org/10.1055/s-0029-1219229.

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30

Farah, Carolina, Mario Vera, Danièle Morin, Dominique Haras, Carlos A. Jerez, and Nicolas Guiliani. "Evidence for a Functional Quorum-Sensing Type AI-1 System in the Extremophilic Bacterium Acidithiobacillus ferrooxidans." Applied and Environmental Microbiology 71, no. 11 (November 2005): 7033–40. http://dx.doi.org/10.1128/aem.71.11.7033-7040.2005.

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ABSTRACT Acidithiobacillus ferrooxidans is one of the main acidophilic chemolithotrophic bacteria involved in the bioleaching of metal sulfide ores. The bacterium-mineral interaction requires the development of biofilms, whose formation is regulated in many microorganisms by type AI-1 quorum sensing. Here, we report the existence and characterization of a functional type AI-1 quorum-sensing system in A. ferrooxidans. This microorganism produced mainly acyl-homoserine lactones (AHL) with medium and large acyl chains and different C-3 substitutions, including 3-hydroxy-C8-AHL, 3-hydroxy-C10-AHL, C12-AHL, 3-oxo-C12-AHL, 3-hydroxy-C12-AHL, C14-AHL, 3-oxo-C14-AHL, 3-hydroxy-C14-AHL, and 3-hydroxy-C16-AHL. A quorum-sensing genetic locus that includes two open reading frames, afeI and afeR, which have opposite orientations and code for proteins with high levels of similarity to members of the acyl synthase (I) and transcriptional regulator (R) protein families, respectively, was identified. Overexpression of AfeI in Escherichia coli and the associated synthesis of AHLs confirmed that AfeI is an AHL synthase. As determined by reverse transcription-PCR, the afeI and afeR genes were transcribed in A. ferrooxidans. The transcription levels of the afeI gene were higher in cells grown in sulfur and thiosulfate media than in iron-grown cells. Phosphate starvation induced an increase in the transcription levels of afeI which correlated with an increase in AHL levels. Two afe boxes which could correspond to the AfeR binding sites were identified upstream of the afeI gene. This is the first report of a functional type AI-1 quorum-sensing system in an acidophilic chemolithotrophic microorganism, and our results provide a very interesting opportunity to explore the control and regulation of biofilm formation during the bioleaching process.

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31

Taguchi, Fumiko, Tomoko Suzuki, Yoshishige Inagaki, Kazuhiro Toyoda, Tomonori Shiraishi, and Yuki Ichinose. "The Siderophore Pyoverdine of Pseudomonas syringae pv. tabaci 6605 Is an Intrinsic Virulence Factor in Host Tobacco Infection." Journal of Bacteriology 192, no. 1 (October 23, 2009): 117–26. http://dx.doi.org/10.1128/jb.00689-09.

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ABSTRACT To investigate the role of iron uptake mediated by the siderophore pyoverdine in the virulence of the plant pathogen Pseudomonas syringae pv. tabaci 6605, three predicted pyoverdine synthesis-related genes, pvdJ, pvdL, and fpvA, were mutated. The pvdJ, pvdL, and fpvA genes encode the pyoverdine side chain peptide synthetase III l-Thr-l-Ser component, the pyoverdine chromophore synthetase, and the TonB-dependent ferripyoverdine receptor, respectively. The ΔpvdJ and ΔpvdL mutants were unable to produce pyoverdine in mineral salts-glucose medium, which was used for the iron-depleted condition. Furthermore, the ΔpvdJ and ΔpvdL mutants showed lower abilities to produce tabtoxin, extracellular polysaccharide, and acyl homoserine lactones (AHLs), which are quorum-sensing molecules, and consequently had reduced virulence on host tobacco plants. In contrast, all of the mutants had accelerated swarming ability and increased biosurfactant production, suggesting that swarming motility and biosurfactant production might be negatively controlled by pyoverdine. Scanning electron micrographs of the surfaces of tobacco leaves inoculated with the mutant strains revealed only small amounts of extracellular polymeric matrix around these mutants, indicating disruption of the mature biofilm. Tolerance to antibiotics was drastically increased for the ΔpvdL mutant, as for the ΔpsyI mutant, which is defective in AHL production. These results demonstrated that pyoverdine synthesis and the quorum-sensing system of Pseudomonas syringae pv. tabaci 6605 are indispensable for virulence in host tobacco infection and that AHL may negatively regulate tolerance to antibiotics.

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32

Barekzi, Nazir, Swati Joshi, Scott Irwin, Todd Ontl, and Herbert P. Schweizer. "Genetic characterization of pcpS, encoding the multifunctional phosphopantetheinyl transferase of Pseudomonas aeruginosa." Microbiology 150, no. 4 (April 1, 2004): 795–803. http://dx.doi.org/10.1099/mic.0.26823-0.

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Fatty acid synthases (primary metabolism), non-ribosomal peptide synthases and polyketide synthases (secondary metabolism) contain phosphopantetheinyl (Ppant)-dependent carrier proteins that must be made functionally active by transfer of the 4′-Ppant moiety from coenzyme A. These reactions are usually catalysed by dedicated Ppant transferases. Although rich in Ppant-dependent carrier proteins, it was previously shown that Pseudomonas aeruginosa possesses only one Ppant transferase, encoded by pcpS, which functions in both primary and secondary metabolism. Consistent with this notion are our findings that pcpS can genetically complement mutations in the Escherichia coli acpS and entD genes, encoding the apo-acyl carrier protein (ACP) synthase of fatty acid synthesis and a Ppant transferase of enterobactin synthesis, respectively. It also complements a Bacillus subtilis sfp mutation affecting a gene encoding a Ppant transferase essential for surfactin synthesis. A pcpS insertion mutant could only be constructed in a strain carrying the E. coli acpS gene on a chromosomally integrated element in trans, implying that the in vitro essentiality of pcpS is due to its requirement for activation of apo-ACP of fatty acid synthesis. The conditional pcpS mutant is non-fluorescent, does not produce pyoverdine and pyochelin, and does not grow in the presence of iron chelators. The data presented here for the first time confirm that PcpS plays an essential role in both fatty acid and siderophore metabolism.

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33

Ren, Kai, Min Wang, Ping Liu, and Lei Wang. "ChemInform Abstract: Iron-Catalyzed Synthesis of Selenoesters from Diselenides and Acyl Chlorides or Acid Anhydrides in the Presence of Magnesium Dust." ChemInform 41, no. 31 (July 9, 2010): no. http://dx.doi.org/10.1002/chin.201031192.

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34

Easmon, Johnny, Gerhard Pürstinger, Gottfried Heinisch, Thomas Roth, Heinz H. Fiebig, Wolfgang Holzer, Walter Jäger, Marcel Jenny, and Johann Hofmann. "Synthesis, Cytotoxicity, and Antitumor Activity of Copper(II) and Iron(II) Complexes of4N-Azabicyclo[3.2.2]nonane Thiosemicarbazones Derived from Acyl Diazines." Journal of Medicinal Chemistry 44, no. 13 (June 2001): 2164–71. http://dx.doi.org/10.1021/jm000979z.

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35

Davies, Stephen G., and G. Lance Gravatt. "Asymmetric synthesis of phenyl alkyl sulphoxides via the non-destructive mediation of the chiral iron acyl [(η5-C5H5)Fe(CO)(PPh3)COCH2Me]." J. Chem. Soc., Chem. Commun., no. 12 (1988): 780–81. http://dx.doi.org/10.1039/c39880000780.

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36

EHLENZ, R., M. NIEGER, K. AIROLA, and K. H. DOETZ. "ChemInform Abstract: Organotransition Metal Modified Sugars. Part 3. Sugar Acyl Iron Complexes: Synthesis and Conformational Studies in Solution and in the Solid State." ChemInform 29, no. 21 (June 22, 2010): no. http://dx.doi.org/10.1002/chin.199821199.

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37

Davies, Stephen G., Narciso M. Garrido, Paul A. McGee, and John P. Shilvock. "Asymmetric synthesis of β-lactams and pseudopeptides via stereoselective conjugate additions of lithium (α-methylbenzyl)allylamide to α,β-unsaturated iron acyl complexes." Journal of the Chemical Society, Perkin Transactions 1, no. 21 (1999): 3105–10. http://dx.doi.org/10.1039/a906633k.

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38

Liebeskind, Lanny S., Richard W. Fengl, and Mark E. Welker. "A practical synthes of α,β-unstaurated iron acyls. Chiral enoate synthesis." Tetrahedron Letters 26, no. 26 (January 1985): 3075–78. http://dx.doi.org/10.1016/s0040-4039(00)98622-2.

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39

Lewenza, Shawn, and Pamela A. Sokol. "Regulation of Ornibactin Biosynthesis andN-Acyl-l-Homoserine Lactone Production by CepR in Burkholderia cepacia." Journal of Bacteriology 183, no. 7 (April 1, 2001): 2212–18. http://dx.doi.org/10.1128/jb.183.7.2212-2218.2001.

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ABSTRACT The CepR-CepI quorum-sensing system has been shown to regulate production of the siderophore ornibactin, extracellular proteases, andN-octanoyl-homoserine-l-lactone (OHL) inBurkholderia cepacia strain K56-2. To examine the effect ofcepIR on production of other siderophores, cepRmutants were constructed in strains that produce pyochelin in addition to salicylic acid and ornibactins. Pc715j-R1 (cepR::tp) hyperproduced ornibactin but produced parental levels of pyochelin and salicylic acid, suggesting that CepR is a negative regulator of ornibactin synthesis but not pyochelin or salicylic acid. Pc715j-R1 was also protease deficient and OHL negative. The effects of cepR on ornibactin biosynthetic genes were examined by constructing cepR pvdA-lacZ and cepR pvdD-lacZ mutants and monitoring β-galactosidase activity. There was an increase in expression of pvdA in thecepR mutant compared to the level in its parent strain in both low- and high-iron media during stationary phase. When the outer membrane protein profiles of a cepR mutant and the wild-type strain were compared on sodium dodecyl sulfate-polyacrylamide gel electrophoresis, there did not appear to be any difference in levels of expression of the ornibactin receptor. Experiments withcepI-lacZ and cepR-lacZ transcriptional fusions indicated that cepI was not expressed in thecepR mutant and that cepR acts as a negative regulator of its own expression. By a thin-layer chromatography assay for N-acyl homoserine lactones, OHL andN-hexanoyl-l-homoserine lactone (HHL) were detectable in K56-2 and Pc715j, both wild-type strains. OHL was not detectable and HHL was only weakly detectable in the cepIand cepR mutants. These results suggest that CepR is both a positive and negative transcriptional regulator and that CepR may influence the expression of ornibactin biosynthetic genes in addition to the expression of the cepIR quorum-sensing system.

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40

Seyferth, Dietmar, and Colin M. Archer. "Novel C-alkylation of a CO-bridged dinuclear iron carbonyl anion: a new synthesis of Fe2(CO)6 complexes containing a bridging acyl ligand." Organometallics 5, no. 12 (December 1986): 2572–74. http://dx.doi.org/10.1021/om00143a037.

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41

Li-Cheng, Song, Liu Rong-Gang, Hu Qing-Mei, Wang Ji-Tao, Liu Xiao-Lan, and Miao Fang-Ming. "Studies on Nucleophilic Substitution Reaction of μ-Acyl Iron-Sulfur Complexes——Synthesis and Structures of Some PPh₃-OR AsPh₃-Substituted μ-Acyl Fe-S Complexes." Acta Physico-Chimica Sinica 6, no. 04 (1990): 449–55. http://dx.doi.org/10.3866/pku.whxb19900412.

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42

Baker, Teresa M., Graham J. Bodwell, Stephen G. Davies, Alison J. Edwards, and Michael R. Metzler. "Asymmetric synthesis of (S)-(−)-methyl tropinate: application of the iron acyl complex (S)-(+)-[(η5-C5H5)Fe(CO)(PPh3)COCH2Ph] as a homochiral phenylacetate enolate equivalent." Tetrahedron 49, no. 25 (January 1993): 5635–47. http://dx.doi.org/10.1016/s0040-4020(01)87273-2.

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43

Davies, Stephen G., Narciso M. Garrido, Paul A. McGee, and John P. Shilvock. "ChemInform Abstract: Asymmetric Synthesis of β-Lactams and Pseudopeptides via Stereoselective Conjugate Additions of Lithium (α-Methylbenzyl)allylamide to α,β-Unsaturated Iron Acyl Complexes." ChemInform 31, no. 12 (June 9, 2010): no. http://dx.doi.org/10.1002/chin.200012110.

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44

Driller, Katrin Marie, Saisuree Prateeptongkum, Ralf Jackstell, and Matthias Beller. "A General and Selective Iron-Catalyzed Aminocarbonylation of Alkynes: Synthesis of Acryl- and Cinnamides." Angewandte Chemie International Edition 50, no. 2 (November 30, 2010): 537–41. http://dx.doi.org/10.1002/anie.201005823.

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45

Luart, Denis, Nathalie le Gall, Jean-Yves Salaün, Loı̈c Toupet, and Hervé des Abbayes. "Synthesis of bis-(acyl, carbamoyl or alkoxycarbonyl) iron monomer or dimer complexes by reaction of oxalyl chloride with various tetracarbonyl ferrates: {Fe[C(O)R](CO)4}−." Inorganica Chimica Acta 291, no. 1-2 (August 1999): 166–77. http://dx.doi.org/10.1016/s0020-1693(99)00024-9.

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46

BAKER, T. M., G. J. BODWELL, S. G. DAVIES, A. J. EDWARDS, and M. R. METZLER. "ChemInform Abstract: Asymmetric Synthesis of (S)-(-)-Methyl Tropinate: Application of the Iron Acyl Complex (S)-(+)-((η5-C5H5)Fe(CO)(PPh3)COCH2Ph) as a Homochiral Phenylacetate Enolate Equivalent." ChemInform 24, no. 44 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199344290.

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47

Driller, Katrin Marie, Saisuree Prateeptongkum, Ralf Jackstell, and Matthias Beller. "ChemInform Abstract: A General and Selective Iron-Catalyzed Aminocarbonylation of Alkynes: Synthesis of Acryl- and Cinnamides." ChemInform 42, no. 20 (April 21, 2011): no. http://dx.doi.org/10.1002/chin.201120078.

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48

Torres‐Ochoa, Rubén O., Alexandre Leclair, Qian Wang, and Jieping Zhu. "Iron‐Catalysed Remote C(sp 3 )−H Azidation of O ‐Acyl Oximes and N ‐Acyloxy Imidates Enabled by 1,5‐Hydrogen Atom Transfer of Iminyl and Imidate Radicals: Synthesis of γ‐Azido Ketones and β‐Azido Alcohols." Chemistry – A European Journal 25, no. 40 (May 10, 2019): 9477–84. http://dx.doi.org/10.1002/chem.201901079.

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49

Ruck-Braun, Karola. "ChemInform Abstract: Iron-Acyl Complexes." ChemInform 30, no. 10 (June 17, 2010): no. http://dx.doi.org/10.1002/chin.199910284.

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50

Pudovik, A. N., V. N. Nazmutdinova, and L. P. Chirkova. "Synthesis of acyl cyanophosprites." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 38, no. 2 (February 1989): 418–19. http://dx.doi.org/10.1007/bf00953644.

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