- Isoflavone glycosides from aerial parts of Artemisia absinthium
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Two new isoflavone glycosides, designated as artemisia bis-isoflavonyl dirhamnoside and artemisia isoflavonyl glucosyl diester, have been isolated from the aerial parts of A. absinthium and their structures established as 7a,7b-bis-[(5a-hydroxy-3′a,4′a-dimethoxyisoflavonyl) (5b,4′b-dihydroxy-3′b-methoxyisoflavonyl)]-4′b-α- Drhamnopyranosyl-(4 → 1)-α-D-rhamnopyranoside and 7,4′-dihydroxyisoflavonyl-7-β-D-glucopyranosyl-(2 → 1)-β-D-glucopyranosyl-(2 → 1)-β-D-glucopyranosyl-(2 → 1)-β-D-glucopyranosyl-6d-(octadec-9′″-enoate)-2d-7″, 11″,15″-trimethylpentadecan-3″,15″-dioic acid-1″-oate on the basis of chemical reactions and spectral data analysis.
- Ahamad,Naquvi,Ali,Mir
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- Chloroacetoxylation of oleic acid - a kinetic study
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The kinetics of the addition reaction of chloroacetic acid to oleic acid (chloroacetoxylation) in the presence of sulfuric acid as a catalyst were investigated. The reactions were carried out at the same concentration of both reactants at various temperatures and catalyst content. The reaction time ranged from 30 min up to 12 h, and the reaction course was observed by determining mainly iodine value, and chlorine content of the oil samples at 30-min intervals. The experimental data fitted the reversible second-first order rate equation for bi-molecular-unimolecular type reactions. The reaction constants of the forward and reverse reactions were obtained at temperatures 70 and 80 °C. The effect of sulfuric acid content on the reaction constant was investigated at 70 and 80 °C.
- Doulia, Danae,Rigas, Fotis,Gimouhopoulos, Kostantinos
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- Hydrothermal deoxygenation of triglycerides over Pd/C aided by in situ hydrogen production from glycerol reforming
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A one-pot catalytic hydrolysis-deoxygenation reaction for the conversion of unsaturated triglycerides and free fatty acids to linear paraffins and olefins is reported. The hydrothermal deoxygenation reactions are performed in hot compressed water at 250 °C over a Pd/C catalyst in the absence of external H2. We show that aqueous-phase reforming (APR) of glycerol and subsequent water-gas-shift reaction result in the in situ formation of H 2. While this has a significant positive effect on the deoxygenation activity, the product selectivity towards high-value, long-chain olefins remains high. With a little H2elp from my friends: A one-pot hydrolysis-deoxygenation reaction for triglycerides and free fatty acids, which is of particular interest for the production of biofuels and value-added chemicals from nonedible or waste fats and oils, is reported. The reaction is performed over palladium on carbon (Pd/C) at 250 °C without additional H2. Instead, in situ H2 production occurs through glycerol reforming and subsequent water-gas-shift reaction with a positive effect on the deoxygenation activity.
- Hollak, Stefan A. W.,Ari?ns, Maxim A.,De Jong, Krijn P.,Van Es, Daan S.
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- Kinetics and pathways for an algal phospholipid (1,2-dioleoyl-sn-glycero-3- phosphocholine) in high-temperature (175-350 °c) water
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We examined the behavior of 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) in high-temperature water at 175, 200, 225, and 350 °C. DOPC hydrolyzed to give oleic acid and a number of phosphorus-containing products. The hydrolysis was catalyzed by oleic and phosphoric acids, which were also reaction products. DOPC formed 1-acyl and 2-acyl lyso-phosphatidylcholine (LPC) along with oleic acid as primary products. LPC subsequently formed other phosphorus-containing intermediates, which finally led to phosphoric acid as the ultimate P-containing product. At 350 °C, phosphoric acid and oleic acid were the only products observed. We observed an ester of oleic acid and glycerol (9-octadecenoic-2,3- dihydroxypropyl ester), which likely formed via the hydrolysis of LPC. A reaction network is proposed to explain the formation of the observed products. A quantitative kinetics model based on the proposed pathways was consistent with the experimental data.
- Changi, Shujauddin,Savage, Phillip E.,Matzger, Adam J.
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- Lipase mimetic cyclodextrins
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Glycerophospholipids (GPLs) perform numerous essential functions in biology, including forming key structural components of cellular membranes and acting as secondary messengers in signaling pathways. Developing biomimetic molecular devices that can detect specific GPLs would enable modulation of GPL-related processes. However, the compositional diversity of GPLs, combined with their hydrophobic nature, has made it challenging to develop synthetic scaffolds that can react with specific lipid species. By taking advantage of the host-guest chemistry of cyclodextrins, we have engineered a molecular device that can selectively hydrolyze GPLs under physiologically relevant conditions. A chemically modified α-cyclodextrin bearing amine functional groups was shown to hydrolyze lyso-GPLs, generating free fatty acids. Lyso-GPLs are preferentially hydrolyzed when part of a mixture of GPL lipid species, and reaction efficiency was dependent on lyso-GPL chemical structure. These findings lay the groundwork for the development of molecular devices capable of specifically manipulating lipid-related processes in living systems.
- Lee, Youngjun,Devaraj, Neal K.
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- Radical nitrile transfer with methanesulfonyl cyanide or P-toluenesulfonyl cyanide to carbon radicals generated from the acyl derivatives of N-hydroxy-2-thiopyridone
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Reaction of methanesulfonyl cyanide or p-toluenesulfonyl cyanide with carbon radicals generated from the acyl derivatives of N-hydroxy-2-thiopyridone gives the corresponding nitriles in high yield. A mechanistic scheme is suggested.
- Barton,Jaszberenyi,Theodorakis
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- Phospholipases a1 from armillaria ostoyae provide insight into the substrate recognition of a/b-hydrolase fold enzymes
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Four enzymes with phospholipase A1(PLA1) activity were purified from the fruiting bodies of the basidiomycete Armillaria ostoyae. The enzymes (PLA1-1, -2, -3 and -4) showed similar isoelectric points (4.3, 3.9, 4.0 and 4.0) and apparent molecular masses in the range of 35-47 kDa. Mass spectrometric analyses of proteolytic fragments revealed sequences homologous to a/b-hydrolase fold enzymes. The enzymes share one conserved region with fungal phospholipases B and the active site sequence with bacterial esterases and PLA1s. PLA1-1 cleaves phospholipids and lysophospholipids with an optimum activity at pH 5.3. In contrast, PLA1-2, -3 and -4 are characterized by broad pH optima in the slightly acidic to neutral range and are additionally capable of hydrolyzing mono- and diglycerides as well as fatty acid methyl esters. All enzymes favor glycerol-based lipids with a single medium-sized fatty acid moiety in the sn-1 position but show reduced activity towards the corresponding 1, 2-diacyl derivatives with bulky long-chain or inflexible saturated fatty acid moieties in the sn-2 position. The enzymes prefer zwitterionic phospholipid substrates and are unable to hydrolyze triglycerides. From the selectivity of these broad-spectrum a/b-hydrolase fold enzymes towards the different classes of their substrates a regiospecific steric hindrance and a head group recognition are concluded.
- Dippe, Martin,Mueller, Mathias Q.,Sinz, Andrea,Ulbrich-Hofmann, Renate
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- Synthesis and properties of ascorbyl esters catalyzed by lipozyme TL im using triglycerides as acyl donors
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Esters of l-ascorbic acid with long-chain fatty acids (E-304) are employed as antioxidants in foods rich in lipids. Although their enzymatic synthesis offers some advantages compared with the current chemical processes, most of the reported methods employ the immobilized lipase from Candida antarctica as biocatalyst and free fatty acids or activated esters as acyl donors. In order to diminish the cost of the process, we have investigated the synthesis of ascorbyl oleate and ascorbyl palmitate esters with the immobilized Thermomyces lanuginosus lipase Lipozyme TL IM-which is significantly less expensive than Novozym 435-and triglycerides as source of fatty acids. Lipozyme TL IM gave rise to a lower yield of 6-O-ascorbyl oleate than Novozym 435 when using triolein (64 vs. 84%) and olive oil (27 vs. 33%) as acyl donors. Both 6-O-ascorbyl oleate and 6-O-ascorbyl palmitate displayed excellent surfactant and antioxidant properties. The Trolox Equivalent Antioxidant Capability values for the oleate and palmitate were 71 and 84%, respectively, of those obtained with l-ascorbic acid; however, both derivatives were able to stabilize soybean oil towards peroxide formation.
- Reyes-Duarte,Lopez-Cortes,Torres,Comelles,Parra,Pena,Ugidos,Ballesteros,Plou
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- Purification and biochemical characterization of an extracellular lipase from Pseudomonas fluorescens MTCC 2421
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An extracellular lipase produced by Pseudomonas fluorescens MTCC 2421 was purified 184.37-fold with a specific activity of 424.04 LU/mg after anion exchange and gel exclusion chromatography. The enzyme is a homomeric protein with an apparent molecular mass of 65.3 kDa. The lipase exhibited hydrolytic resistance toward triglycerides with longer fatty acyl chain length containing unsaturation as evident from the lower Vmax (0.23 mM/mg/min) of the lipase toward glycerol trioleate (C18:1n9) compared with the fatty acid triglycerides having short to medium carbon chain lengths (C 18:0-12:0, Vmax 0.32-0.51 mM/mg/min). This indicates a preferential specificity of the lipase toward cleaving shorter carbon chain length fatty acid triglycerides. The lipase exhibited optimum activity at 40 °C and pH 8.0, respectively. A combination of Ca2+ and sorbitol induced a synergistic effect on the thermostability of lipase with a significantly high residual activity (100%) after 30 min at 40 °C, as compared to 90.6% after incubation with Ca2+ alone. The lipase activity was inhibited by Cu2+ and Fe2+ (42 and 48%,respectively) at 10 mM. The enzyme lost 31% of its initial activity by 0.001 mM EDTA and 42% by 0.1 mM EDTA. Significant reduction in lipase activity was apparent by 2-mercaptoethanol and phenylmethanesulfonyl fluoride at diluted concentration (0.001 mM), thereby indicating an important role of sulfhydryl groups in the catalytic mechanism.
- Chakraborty, Kajal,Paulraj
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- Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials
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A set of compounds from non-edible fat waste was prepared and their thermal behavior was studied. The fat was hydrolyzed and crystallized in a simple and robust process to yield palmitic acid-stearic acid (PA-SA) mixtures. The PA-SA mass ratios determined by GC-FID (gas chromatography-flame ionization detection) were similar to those reported for eutectic mixtures of PCMs (phase change materials). DSC (differential scanning calorimetry) results indicated that the melting and solidification temperatures were around 55 °C and 52 °C and the latent heat of the crystallized fractions measured was around 180 kJ kg-1. The thermal cycling reliability of the eutectic mixtures was also tested during 1000 melting/freezing cycles. The loss in melting and solidification enthalpies was below 14% in all mixtures showing a promising behavior for PCM applications. Additionally, the unsaturated fatty acids were recovered and transformed to threo-9,10-dihydroxystearic acid (DHSA) and some of their inorganic salts, which were analyzed by FT-IR (Fourier transform-infrared spectroscopy) and tested for the first time using the DSC technique.
- Gallart-Sirvent, Pau,Martín, Marc,Villorbina, Gemma,Balcells, Mercè,Solé, Aran,Barrenche, Camila,Cabeza, Luisa F.,Canela-Garayoa, Ramon
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- Improving the activity and stability of Yarrowia lipolytica lipase Lip2 by immobilization on polyethyleneimine-coated polyurethane foam
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In this study, polyurethane foam (PUF) was used for immobilization of Yarrowia lipolytica lipase Lip2 via polyethyleneimine (PEI) coating and glutaraldehyde (GA) coupling. The activity of immobilized lipases was found to depend upon the size of the PEI polymers and the way of GA treatment, with best results obtained for covalent-bind enzyme on glutaraldehyde activated PEI-PUF (MW 70,000 Da), which was 1.7 time greater activity compared to the same enzyme immobilized without PEI and GA. Kinetic analysis shows the hydrolytic activity of both free and immobilized lipases on triolein substrate can be described by Michaelis-Menten model. The Km for the immobilized and free lipases on PEI-coated PUF was 58.9 and 9.73 mM, respectively. The Vmax values of free and immobilized enzymes on PEI-coated PUF were calculated as 102 and 48.6 U/mg enzyme, respectively. Thermal stability for the immobilization preparations was enhanced compared with that for free preparations. At 50 C, the free enzyme lost most of its initial activity after a 30 min of heat treatment, while the immobilized enzymes showed significant resistance to thermal inactivation (retaining about 70% of its initial activity). Finally, the immobilized lipase was used for the production of lauryl laurate in hexane medium. Lipase immobilization on the PEI support exhibited a significantly improved operational stability in esterification system. After re-use in 30 successive batches, a high ester yield (88%) was maintained. These results indicate that PEI, a polymeric bed, could not only bridge support and immobilized enzymes but also create a favorable micro-environment for lipase. This study provides a simple, efficient protocol for the immobilization of Y. lipolytica lipase Lip2 using PUF as a cheap and effective material.
- Cui, Caixia,Tao, Yifeng,Li, Lingli,Chen, Biqiang,Tan, Tianwei
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- Antiparasitic Ovalicin Derivatives from Pseudallescheria boydii, a Mutualistic Fungus of French Guiana Termites
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Social insects are in mutualism with microorganisms, contributing to their resistance against infectious diseases. The fungus Pseudallescheria boydii SNB-CN85 isolated from termites produces ovalicin derivatives resulting from the esterification of the less hindered site of the ovalicin epoxide by long-chain fatty acids. Their structures were elucidated using spectroscopic analysis and semisynthesis from ovalicin. For ovalicin, these compounds displayed antiprotozoal activities against Plasmodium falciparum and Trypanosoma brucei, with IC50 values of 19.8 and 1.1 μM, respectively, for the most active compound, i.e., ovalicin linoleate. In parallel, metabolomic profiling of a collection of P. boydii strains associated with termites made it possible to highlight this class of compounds together with tyroscherin derivatives in all strains. Finally, the complete genome of P. boydii strains was obtained by sequencing, and the cluster of potential ovalicin and ovalicin biosynthesis genes was annotated. Through these metabolomic and genomic analyses, a new ovalicin derivative named boyden C, in which the 6-membered ring of ovalicin was opened by oxidative cleavage, was isolated and structurally characterized.
- Elie, Nicolas,Eparvier, Véronique,Grayfer, Tatyana,Grellier, Philippe,Hebra, Téo,Leman-Loubière, Charlotte,Sorres, Jonathan,Stien, Didier,Touboul, David
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- Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer
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The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the presence of vulnerable secondary alcohols and tert-butanesulfinamides.
- Tan, Wen-Yun,Lu, Yi,Zhao, Jing-Feng,Chen, Wen,Zhang, Hongbin
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supporting information
p. 6648 - 6653
(2021/09/08)
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- Biochemical and biophysical characterisation of a small purified lipase from Rhizopus oryzae ZAC3
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The characteristics of a purified lipase from Rhizopus oryzae ZAC3 (RoL-ZAC3) were investigated. RoL-ZAC3, a 15.8 kDa protein, which was optimally active at pH 8 and 55 °C had a half-life of 126 min at 60 °C. The kinetic parameters using p-nitrophenylbuty
- Ayinla, Zainab A.,Ademakinwa, Adedeji N.,Gross, Richard A.,Agboola, Femi K.
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- Identification and α -Glucosidase Inhibitory Activity of Meroterpenoids from Hericium erinaceus
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Hericium erinaceus is a very popular edible and medicinal mushroom used for the treatment of enervation and gastrointestinal diseases in Eastern Asia. Chemical investigation on the fruiting body of Hericium erinaceus led to the isolation of 4 new (1 - 4) and 10 known meroterpenoids (5 - 14). The structures of new compounds were determined via analysis of NMR and MS data in combination with chemical derivatization. The inhibitory activities of 1 - 14 against α -glucosidase were evaluated using p -nitrophenyl- α -D-glucopyranoside, sucrose, or maltose as substrate. Compounds 6, 9, 11 - 13 were demonstrated to show the α -glucosidase inhibitory activities. This work confirms the potential of H. erinaceus in the treatment of diabetes.
- Bao, Li,Chen, Baosong,Han, Junjie,Liu, Hongwei,Ma, Ke,Wang, Wenzhao
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p. 571 - 578
(2020/06/03)
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- Light-Driven Enzymatic Decarboxylation of Fatty Acids
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The photoenzymatic decarboxylation of fatty acids to alkanes is proposed as an alternative approach for the synthesis of biodiesel. By using a recently discovered photodecarboxylase from Chlorella variabilis NC64A (CvFAP) we demonstrate the irreversible preparation of alkanes from fatty acids and triglycerides. Several fatty acids and their triglycerides are converted by CvFAP in near-quantitative yield and exclusive selectivity upon illumination with blue light. Very promising turnover numbers of up to 8000 were achieved in this proof-of-concept study.
- Huijbers, Mieke M. E.,Zhang, Wuyuan,Tonin, Fabio,Hollmann, Frank
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supporting information
p. 13648 - 13651
(2018/09/21)
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- Alteration of Chain Length Selectivity of Candida antarctica Lipase A by Semi-Rational Design for the Enrichment of Erucic and Gondoic Fatty Acids
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Biotechnological strategies using renewable materials as starting substrates are a promising alternative to traditional oleochemical processes for the isolation of different fatty acids. Among them, long chain mono-unsaturated fatty acids are especially interesting in industrial lipid modification, since they are precursors of several economically relevant products, including detergents, plastics and lubricants. Therefore, the aim of this study was to develop an enzymatic method in order to increase the percentage of long chain mono-unsaturated fatty acids from Camelina and Crambe oil ethyl ester derivatives, by using selective lipases. Specifically, the focus was on the enrichment of gondoic (C20:1 cisΔ11) and erucic acid (C22:1 cisΔ13) from Camelina and Crambe oil derivatives, respectively. The pursuit of this goal entailed several steps, including: (i) the choice of a suitable lipase scaffold to serve as a protein engineering template (Candida antarctica lipase A); (ii) the identification of potential amino acid targets to disrupt the binding tunnel at the adequate location; (iii) the design, creation and high-throughput screening of lipase mutant libraries; (iv) the study of the selectivity towards different chain length p-nitrophenyl fatty acid esters of the best hits found, as well as the analysis of the contribution of each amino acid change and the outcome of combining several of the aforementioned residue alterations and, finally, (v) the selection and application of the most promising candidates for the fatty acid enrichment biocatalysis. As a result, enrichment of C22:1 from Crambe ethyl esters was achieved either, in the free fatty acid fraction (wt, 78%) or in the esterified fraction (variants V1, 77%; V9, 78% and V19, 74%). Concerning the enrichment of C20:1 when Camelina oil ethyl esters were used as substrate, the best variant was the single mutant V290W, which doubled its content in the esterified fraction from approximately 15% to 34%. A moderately lower increase was achieved by V9 and its two derived triple mutant variants V19 and V20 (27%). (Figure presented.).
- Zorn, Katja,Oroz-Guinea, Isabel,Brundiek, Henrike,D?rr, Mark,Bornscheuer, Uwe T.
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p. 4115 - 4131
(2018/10/02)
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- Oxidative Transformations of Biosourced Alcohols Catalyzed by Earth-Abundant Transition Metals
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The catalytic acceptorless dehydrogenative oxidation of biosourced alcohols into carboxylic acid salts was achieved using earth-abundant Fe and Mn complexes that feature aliphatic PNP pincer ligands in good to excellent yields. The Fe derivatives were characterized by using 57Fe NMR spectroscopy. Mn pincer catalysts are catalytically more efficient than their Fe counterparts thanks to their robustness under basic conditions. Attempts to generate aldehydes from alcohols were not successful using the Fe and Mn species, but a commercially available Ru analogue achieves this transformation selectively under very mild conditions in the presence of a large excess of acetone as a hydrogen acceptor.
- Nguyen, Duc Hanh,Morin, Yohann,Zhang, Lei,Trivelli, Xavier,Capet, Frédéric,Paul, Sébastien,Desset, Simon,Dumeignil, Franck,Gauvin, Régis M.
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p. 2652 - 2660
(2017/07/28)
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- Revealing the Roles of Subdomains in the Catalytic Behavior of Lipases/Acyltransferases Homologous to CpLIP2 through Rational Design of Chimeric Enzymes
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The lipases/acyltransferases homologous to CpLIP2 of Candida parapsilosis efficiently catalyze acyltransfer reactions in lipid/water media with high water activity (aW>0.9). Two new enzymes of this family, CduLAc from Candida dubliniensis and CalLAc8 from Candida albicans, were characterized. Despite 82 % sequence identity, the two enzymes have significant differences in their catalytic behaviors. In order to understand the roles played by the different subdomains of these proteins (main core, cap and C-terminal flap), chimeric enzymes were designed by rational exchange of cap and C-terminal flap, between CduLAc and CalLAc8. The results show that the cap region plays a significant role in substrate specificity; the main core was found to be the most important part of the protein for acyltransfer ability. Similar exchanges were made with CAL-A from Candida antarctica, but only the C-terminal exchange was successful. Yet, the role of this domain was not clearly elucidated, other than that it is essential for activity.
- Jan, Anne-Hélène,Dubreucq, éric,Subileau, Maeva
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p. 941 - 950
(2017/05/26)
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- NOVEL GENE DERIVED FROM MUD FLAT METAGENOME AND NOVEL PROTEIN OBTAINED THEREFROM SHOWING COACTIVITY OF PHOSPHOLIPASE AND LIPASE
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The present invention relates to a novel gene derived from a tidal flat metagenome, and a novel protein obtained therefrom showing the coactivity of phospholipase and lipase. Specifically, the novel gene isolated from the metagenome library of tidal flat sedimentsand the protein having phospholipase and lipase activities encoded from the novel gene: are expressed in a water-soluble form to be mass-producible; enable ultra high-purity protein to be obtained through single step purification using an Ni-NTA column; show good activity in the pH range of 5 ?? 10; maintain good low temperature activity and stability up to a temperature of 3°C to 40°C; and have high resistance against various organic solvents. Therefore, the novel gene and the protein can be usefully used for various industrial fields such as the purification and conversion of oil and fat, bio-medicine, and fine chemistry.
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Paragraph 0083-0084
(2016/03/14)
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- New biobased tetrabutylphosphonium ionic liquids: Synthesis, characterization and use as a solvent or co-solvent for mild and greener Pd-catalyzed hydrogenation processes
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Phosphonium-based Ionic Liquids (PhosILs) with natural organic derived anions (l-lactate, l-tartrate, malonate, succinate, l-malate, pyruvate, d-glucuronate, d-galacturonate, ferulate, p-coumarate) were easily prepared by acid-base method from tetrabutylphosphonium hydroxide and an excess of the corresponding acid with good yields. Their characterization was realized through classical NMR, IR and elemental analysis techniques; their viscosity and ATG parameters were also determined. These ionic liquids showed good performance and recyclability in the selective Pd-catalyzed hydrogenation of alkenes, polyenes like linoleic acid and enantioselective hydrogenation of unsaturated ketones such as isophorone at room temperature under atmospheric H2 pressure. Furthermore, NMR studies leading to computational calculations were performed to establish easily the composition of the resulting mixture obtained through the hydrogenation of linoleic acid.
- Hayouni, Safa,Robert, Anthony,Ferlin, Nadège,Amri, Hassen,Bouquillon, Sandrine
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p. 113583 - 113595
(2016/12/16)
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- Photocatalytic degradation of ciprofloxacin by synthesized TiO2 nanoparticles on montmorillonite: Effect of operation parameters and artificial neural network modeling
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TiO2/MMT nanocomposite was synthesized and characterized by X-ray diffraction (XRD), fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), Energy-dispersive X-ray spectroscopy (EDX), transmission electron microscopy (TEM), X-ray fluorescence (XRF) and Brunauer-Emmett-Teller (BET) techniques. The average size of TiO2 nanoparticles was decreased from 60-80 nm to 40-60 nm through the immobilization on MMT. The main influential factors such as the TiO2/MMT dose, ciprofloxacin (CIP) concentration, pH of the solution, UV light regions, reusability of the catalyst and electrical energy determination were studied. The addition of radical scavengers (e.g. chloride, iodide, sulfate and bicarbonate) and enhancers (e.g. hydrogen peroxide, potassium iodate and peroxydisulfate) on the degradation efficiency was studied. The predicted data from the designed artificial neural network model were found to be in a good agreement with the experimental data (R2 = 0.9864). The main intermediates of CIP degradation were determined by GC-Mass spectrometry.
- Hassani, Aydin,Khataee, Alireza,Karaca, Semra
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p. 149 - 161
(2015/09/15)
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- Cytotoxic ceramides from the Red Sea sponge Spheciospongia vagabunda
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Extracts of Egyptian marine organisms from the Red Sea were screened for their anticancer activity using sulforhodamine B assay. The extract of the Red Sea sponge Spheciospongia vagabunda possessed promising anticancer activity against HepG2 (liver cancer cell line) and MCF-7 (breast cancer cell line). Isolation of three new ceramides: N-[(2S,3S,4R)-1,3,4-trihydroxytetradecan-2-yl] tridecanamide (1), (R)-2′-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxypentacosan-2-yl] octadecanamide (2) and (R,Z)-2′-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxytricosan-2-yl) nonadec-10-enamide (3) was accomplished via bioassay-guided fractionation. Structure elucidation was achieved using spectroscopic techniques, including 1D and 2D NMR and HRMS. Compounds 2 and 3 displayed high potential cytotoxicity against HepG2 (IC50 24.7 and 21.3 μM, respectively) and MCF-7 (IC50 26.8 and 29.8 μM, respectively), compared with doxorubicin as control drug.
- Eltamany, Enas Elsayed,Ibrahim, Amany K.,Radwan, Mohamed M.,Elsohly, Mahmoud A.,Hassanean, Hashim A.,Ahmed, Safwat A.
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p. 3467 - 3473
(2015/08/03)
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- Safe Removal of the Allyl Protecting Groups of Allyl Esters using a Recyclable, Low-Leaching and Ligand-Free Palladium Nanoparticle Catalyst
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A safe, facile and low-leaching (up to 0.04ppm) method has been developed for the removal of allyl, prenyl and benzyl protecting groups from the corresponding esters, using a sulfur-modified gold-supported palladium (SAPd) nanoparticle catalyst, which is known to be non-flammable. The catalyst itself was found to be recyclable and the reaction appeared to proceed on the surface of the SAPd.
- Takagi, Koji,Fukuda, Hayato,Shuto, Satoshi,Otaka, Akira,Arisawa, Mitsuhiro
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supporting information
p. 2119 - 2124
(2015/06/23)
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- Electrochemistry for biofuel generation: Transformation of fatty acids and triglycerides to diesel-like olefin/ether mixtures and olefins
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Abstract Electroorganic synthesis can be exploited for the production of biofuels from fatty acids and triglycerides. With Coulomb efficiencies (CE) of up to 50%, the electrochemical decarboxylation of fatty acids in methanolic and ethanolic solutions leads to the formation of diesel-like olefin/ether mixtures. Triglycerides can be directly converted in aqueous solutions by using sonoelectrochemistry, with olefins as the main products (with a CE of more than 20%). The latter reaction, however, is terminated at around 50% substrate conversion by the produced side-product glycerol. An energy analysis shows that the electrochemical olefin synthesis can be an energetically competitive, sustainable, and - in comparison with established processes - economically feasible alternative for the exploitation of fats and oils for biofuel production. From fat to fuel: Electrochemical decarboxylation of fatty acids and triglycerides leads to the formation of olefins and ethers (see scheme). This electroorganic synthesis is an energetically competitive, sustainable, and economically feasible alternative for the exploitation of fats and oils for biofuel production.
- Dos Santos, Tatiane R.,Harnisch, Falk,Nilges, Peter,Schr?der, Uwe
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p. 886 - 893
(2015/06/02)
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- METHOD FOR PRODUCING CARBOXYLIC ACID AND ALCOHOL BY HYDROLYSIS OF ESTER
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As shown by the following formula (1), after methyl laurate (2 mmol) and water (8 mL) are added to an ammonium pyrosulfate catalyst (5 mol%), a hydrolysis reaction of methyl laurate is carried out by heating for 24 hours at 60°C while stirring is performed, so that lauric acid can be obtained with a yield of 86%.
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Paragraph 0063; 0064; 0065
(2014/11/13)
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- A high-detergent-performance, cold-adapted lipase from Pseudomonas stutzeri PS59 suitable for detergent formulation
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A high-detergent-performance and cold-adapted lipase was purified and characterised from Pseudomonas stutzeri PS59, which was isolated from Daqing oil fields (Heilongjiang, PR China). The lipase was purified to homogeneity using ammonium sulphate precipitation, dialysis, freeze-drying, ion exchange chromatography and gel filtration chromatography. The molecular weight of the lipase was approximately 55 kDa, as measured by SDS-PAGE. The lipase showed optima activity at pH 8.5 and 20 C. The lipase activity was activated by metal ions, such as Ca2+ and Mn2+, and surfactants, such as Tween 80, Tween 20, sodium dodecyl benzene sulfonate and urea. Oxidising agents, such as H2O2 and NaClO, were found to have little effect on the activity of the lipase, and most organic solvents can enhance the activity of the lipase. The broad substrate specificity and the compatibility of the lipase in the presence of surfactants, oxidising agents, and other detergent additives clearly indicate its potential application in the laundry industry. The hydrolysis resolution of (R,S)-ethyl 2-methylbutyrate by P. stutzeri PS59 lipase was carried out with the yield of 31.2% for R-ethyl 2-methylbutyrate, the enantiomeric excess of residual substrate (ees) was 85.7%. Thus, the lipase also showed an attractive potency for application in biocatalysis.
- Li, Xiao-Lu,Zhang, Wen-Hui,Wang, Ying-Dong,Dai, Yu-Jie,Zhang, Hui-Tu,Wang, Yue,Wang, Hai-Kuan,Lu, Fu-Ping
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- Shape and transition state selective hydrogenations using egg-shell Pt-MIL-101(Cr) catalyst
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The use of the metal organic framework MIL-101(Cr) as support for Pt nanoparticles is evaluated in three selective hydrogenation reactions. Homogenous Pt nanoparticles of ～4 nm can be formed inside the porosity of MIL-101(Cr) in close contact with the Cr trimers in an egg-shell configuration by a wet impregnation procedure combined with sonication. The catalyst is applied in the selective hydrogenations of olefin mixtures, benzonitrile, and linoleic acid. In the case of an olefin mixture, 1-octene is selectively hydrogenated over 1-hexadecene, attributed to diffusion limitations that favor the hydrogenation of the smaller substrate. In the case of benzonitrile hydrogenation, benzylamine is selectively formed over dibenzylamine attributed to transition state selectivity. In the hydrogenation of linoleic acid, selectivities were similar to that for platinum on alumina.
- Khajavi, Hossein,Stil, Hans A.,Kuipers, Herman P. C. E.,Gascon, Jorge,Kapteijn, Freek
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p. 2617 - 2626
(2013/11/19)
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- A convenient approach for the deprotection and scavenging of the PMB group using POCl3
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A convenient and high yielding approach for the deprotection and scavenging of the p-methoxybenzyl (PMB) group in PMB ethers and PMB esters was developed using POCl3 as the reagent. 4-Methoxybenzyl chloride, a starting material used for the preparation of PMB ethers and esters was regenerated in the deprotection step. This mild and selective procedure tolerates several acid sensitive functional groups. The Royal Society of Chemistry 2013.
- Ilangovan, Andivelu,Saravanakumar, Shanmugasundar,Malayappasamy, Subramani,Manickam, Govindaswamy
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p. 14814 - 14828
(2013/09/02)
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- New chemical constituents from oryza sativa straw and their algicidal activities against blue-green algae
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Five new constituents, 5,4′-dihydroxy-7,3′-dimethoxyflavone- 4′-O-β-d-xylopyranosyl-(2a→1b)-2a-O-β-d-xylopyranosyl- (2b→1c)-2b-O-β-d-xylopyranosyl-2c-octadecanoate (1), 5,4′-dihydroxy-7,3′-dimethoxyflavone-4′-O-α-d- xylopyranosyl-(2a→1b)-2a-O-α-d-xylopyranosyl-(2b→1c) -2b-O-α-d-xylopyranosyl-(2c→1d)-2c-O-α-d-xylopyranosyl-2d- octadecanoate (2), kaempferol-3-O-α-d-xylopyranosyl-(2a→1b)-2a-O- α-d-xylopyranosyl-(2b→1c)-2b-O-α-d-xylopyranosyl-(2c→1d) -2c-O-α-d-xylopyranosyl-2d-hexadecanoate (3), methyl salicylate-2-O- α-d-xylopyranosyl-(2a→1b)-2a-O-α-d-xylopyranosyl-(2b→1c) -2b-O-α-d-xylopyranosyl-(2c→1d)-2c-O-α-d-xylopyranosyl- (2d→1e)-2d-O-α-d-xylopyranosyl-(2e→1f)-2e-O-α-d- xylopyranosyl-(2f→1g)-2f-O-α-d-xylopyranosyl-(2g→1h) -2g-O-α-d-xylopyranosyl-2h-geranilan-8′,10′-dioic acid-1′-oate (4), and oleioyl-β-d-arabinoside (5), along with eight known compounds, were isolated from a methanol extract of Oryza sativa straw. The structures of the new compounds were elucidated using one- and two-dimensional NMR spectroscopies in combination with IR, ESI/MS, and HR-ESI/FTMS. In bioassays with blue-green algae, the efficacies of the algicidal activities of the five new compounds (1-5) were evaluated at concentrations of 1, 10, and 100 mg/L. Compound 5 had the highest growth inhibition (92.6 ± 0.3%) for Microcystis aeruginosa UTEX 2388 at a concentration of 100 ppm (mg/L). Compound 5 has high potential for the ecofriendly control of weeds and algae harmful to water-logged rice.
- Ahmad, Ateeque,Kim, Seung-Hyun,Ali, Mohd,Park, Inmyoung,Kim, Jin-Seog,Kim, Eun-Hye,Lim, Ju-Jin,Kim, Seul-Ki,Chung, Ill-Min
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p. 8039 - 8048
(2013/09/23)
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- Formation of lipase Candida sp. 99-125 CLEAs in mesoporous silica: Characterization and catalytic properties
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Mesoporous silica (MPS) was synthesized and used as a support for lipase Candida sp. 99-125 immobilization. The immobilization procedure was simple and effective: lipase Candida sp. 99-125 was first immobilized in the MPS by adsorption (named ADL@MPS), then chemical crosslinking was conducted for stabilizing the lipase and inhibiting leakage, and cross-linked enzyme aggregates (CLEAs) of Candida sp. 99-125 lipase in the MPS were obtained (named CLL@MPS). The stability of ADL@MPS and CLL@MPS was investigated. Compared with ADL@MPS and native lipase, CLL@MPS showed outstanding stability under vigorous shaking conditions and the thermal stability of CLL@MPS in the presence of organic solvents was also improved. Additionally, CLL@MPS exhibited high catalytic performance in hydrolysis, esterification, and transesterification reactions with increased stability and recyclability. The Royal Society of Chemistry.
- Gao, Jing,Shi, Lianlian,Jiang, Yanjun,Zhou, Liya,He, Ying
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p. 3353 - 3359
(2013/12/04)
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- Mechanistic study of the synthesis of CdSe nanocrystals: Release of selenium
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We outline a reaction pathway for the cleavage of the P=Se bond in trialkylphosphine selenide during the synthesis of CdSe nanocrystals. The reaction between cadmium carboxylate and trimethylphosphine selenide in the presence of an alcohol produces alkoxytrimethylphosphonium (2). Control experiments and density functional theory calculations suggested that the cleavage of the P=Se bond is initiated by nucleophilic attack of carboxylate on a Cd2+-activated phosphine selenide to produce an acyloxytrialkylphosphonium intermediate (1), which is converted to 2 in the presence of an alcohol.
- Garcia-Rodriguez, Raul,Liu, Haitao
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supporting information; experimental part
p. 1400 - 1403
(2012/03/12)
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- Unusual reactivity of dimethylsulfoxonium methylide with esters
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The dimethylsulfoxonium methylide was treated with esters under mild conditions to rapidly afford the corresponding carboxylic acids at room temperature. Moreover, by performing the procedure on enantiopure substrates, it was demonstrated that the reaction occurs without racemization. 18O-labeled reagents showed that the reaction does not proceed through an ester hydrolysis mechanism. The reactions are characterized by an unusual reactivity of the dimethylsulfoxonium methylide. This methodology is general and can be considered a valid alternate route for ester cleavage when a substrate is sensitive to hydrolysis conditions.
- Leggio, Antonella,De Marco, Rosaria,Perri, Francesca,Spinella, Mariagiovanna,Liguori, Angelo
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supporting information; experimental part
p. 114 - 118
(2012/02/14)
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- N,N-diarylammonium pyrosulfate as a highly effective reverse micelle-type catalyst for hydrolysis of esters
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Reverse micelle-type N,N-diarylammonium pyrosulfate (3-5 mol %) efficiently catalyzes the hydrolysis of esters (up to 100 mmol scale) under organic solvent-free conditions. The present method is successfully applied to the hydrolysis of various esters without the decomposition of the base-sensitive moieties and without any loss of optical purity for α-heterosubstituted carboxylic acids.
- Koshikari, Yoshiki,Sakakura, Akira,Ishihara, Kazuaki
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supporting information; experimental part
p. 3194 - 3197
(2012/07/31)
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- A thermoalkaliphilic halotolerant esterase from Rhodococcus sp. LKE-028 (MTCC 5562): Enzyme purification and characterization
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A newly isolated Rhodococcus sp. LKE-028 (MTCC 5562) from soil samples of Gangotri region of Uttarakhand Himalayan produced a thermostable esterase. The enzyme was purified to homogeneity with purification fold 62.8 and specific activity 861.2 U mg-1 proteins along with 26.7% recovery. Molecular mass of the purified enzyme was 38 kDa and values of Km and V max were 525 nM and 1666.7 U mg-1 proteins, respectively. The esterase was active over a broad range of temperature (40-100 °C) and pH (7.0-12.0). The esterase was most active at pH 11.0. The optimum temperature of enzyme activity was 70°C and the enzyme was completely stable after 3 h pre-incubation at 60°C. Metal ions like Ca2+, Mg2+ and Co2+ stimulated enzyme activities. Purified esterase remarkably retained its activity with 10 M NaCl. Enzyme activity was slightly increased in presence of non-polar detergents (Tween 20, Tween 80 and Triton X 100), and compatible with oxidizing agents (H2O2) and reducing agents (β-mercaptoethanol). Activities of the enzyme was stimulated in presence of organic solvents like DMSO, benzene, toluene, methanol, ethyl alcohol, acetone, isoamyl alcohol after 10 days long incubation. The enzyme retained over 75% activity in presence of proteinase K. Besides hyperthermostability and halotolerancy the novelty of this enzyme is its resistance against protease.
- Kumar, Lokendra,Singh, Balvinder,Adhikari, Dilip Kumar,Mukherjee, Joydeep,Ghosh, Debashish
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experimental part
p. 983 - 991
(2012/08/28)
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- Hydrothermal decarboxylation and hydrogenation of fatty acids over Pt/C
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We report herein on the conversion of saturated and unsaturated fatty acids to alkanes over Pt/C in high-temperature water. The reactions were done with no added H2. The saturated fatty acids (stearic, palmitic, and lauric acid) gave the corresponding decarboxylation products (n-alkanes) with greater than 90% selectivity, and the formation rates were independent of the fatty acid carbon number. The unsaturated fatty acids (oleic and linoleic acid) exhibited low selectivities to the decarboxylation product. Rather, the main pathway was hydrogenation to from stearic acid, the corresponding saturated fatty acid. This compound then underwent decarboxylation to form heptadecane. On the basis of these results, it appears that this reaction system promotes in situ H 2 formation. This hydrothermal decarboxylation route represents a new path for using renewable resources to make molecules with value as liquid transportation fuels.
- Fu, Jie,Lu, Xiuyang,Savage, Phillip E.
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experimental part
p. 481 - 486
(2012/02/14)
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- Benzofurans from styrax agrestis as acetylcholinesterase inhibitors: Structure-activity relationships and molecular modeling studies
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An extract of Styrax agrestis fruits, collected in Vietnam, significantly inhibited acetylcholinesterase (AChE) in vitro. Bioassay-guided fractionation revealed three new egonol-type benzofurans: egonol-9(Z),12(Z) linoleate (1), 7-demethoxyegonol-9(Z),12(Z) linoleate (2), and 7-demethoxyegonol oleate (4). Ten known egonol-type benzofurans were also isolated (3, 5, 6-13). In order to better understand structure-activity relationships in this series, egonol derivatives 14-19 were prepared by chemical modifications and evaluated for their inhibition of AChE, butyrylcholinesterase (BChE), and AChE-induced Aβ aggregation. Compounds 1-4 were the most potent inhibitors of the series, which exhibited inhibitory activity against AChE (IC50 1.4-3.1 μM) and, for 1, Aβ aggregation (77.6%). Molecular docking studies were also performed to investigate interaction of these compounds with the active site of AChE.
- Liu, Jiawei,Dumontet, Vincent,Simonin, Anne-Laure,Iorga, Bogdan I.,Guerineau, Vincent,Litaudon, Marc,Nguyen, Van Hung,Gueritte, Francoise
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body text
p. 2081 - 2088
(2011/12/14)
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- Fatty acid esters from roots of amaranthus hybridus linn
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New fatty acid esters were isolated from ethanolic extract of roots of Amaranthus hybridus Linn. (Amaranthaceae). The structures of these compounds were established on the basis of the detailed chemical reaction and spectral analysis as 8'-hydroxynonadecanyl-n-decanoate (1), n-docos-11-enoic acid (2), n-pentacosonyl-n-octadec-9-enoate (3), n-tricosanyl-n-octadec-9,12-dienoate (4).
- Singh, Sumitra,Singh, Sandeep,Sharma, Surendra Kumar,Ali, Mohammad
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body text
p. 232 - 234
(2011/11/30)
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- Methods of Treating Dermatological Disorders and Inducing Interferon Biosynthesis With Shorter Durations of Imiquimod Therapy
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Pharmaceutical Formulations and Methods for the Topical and/or transdermal delivery of imiquimod, including creams, ointments and pressure-sensitive adhesive compositions to treat dermatological disorders, namely, viral infections, such as Type I or Type II Herpes simplex infections and genital and perianal warts, actinic keratosis and superficial basal cell carcinoma, and to induce interferon biosynthesis to achieve an antiviral effect, with shorter durations of therapy, than currently approved for imiquimod by the Food and Drug Administration (“FDA”).
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- Biochemical characterization of the cutinases from Thermobifida fusca
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Thermobifida fusca produces two cutinases which share 93% identity in amino acid sequence. In the present study, we investigated the detailed biochemical properties of T. fusca cutinases for the first time. For a better comparison between bacterial and fungal cutinases, recombinant Fusarium solani pisi cutinase was subjected to the similar analysis. The results showed that both bacterial and fungal cutinases are monomeric proteins in solution. The bacterial cutinases exhibited a broad substrate specificity against plant cutin, synthetic polyesters, insoluble triglycerides, and soluble esters. In addition, the two isoenzymes of T. fusca and the F. solani pisi cutinase are similar in substrate kinetics, the lack of interfacial activation, and metal ion requirements. However, the T. fusca cutinases showed higher stability in the presence of surfactants and organic solvents. Considering the versatile hydrolytic activity, good tolerance to surfactants, superior stability in organic solvents, and thermostability demonstrated by T. fusca cutinases, they may have promising applications in related industries.
- Chen, Sheng,Su, Lingqia,Billig, Susan,Zimmermann, Wolfgang,Chen, Jian,Wu, Jing
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experimental part
p. 121 - 127
(2010/10/19)
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- Fatty acid desaturation and elongation reactions of trichoderma sp. 1-OH-2-3
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The fatty acid desaturation and elongation reactions catalyzed by Trichoderma sp. 1-OH-2-3 were investigated. This strain converted palmitic acid (16:0) mainly to stearic acid (18:0), and further to oleic acid (c9-18:1), linoleic acid (c9,c12-18:2), and α-linolenic acid (c9,c12,c15-18:3) through elongation, and Δ9, Δ12, and Δ15 desaturation reactions, respectively. Palmitoleic acid (c9-16:1) and cis-9,cis-12- hexadecadienoic acid were also produced from 16:0 by the strain. This strain converted n-tridecanoic acid (13:0) to cis-9-heptadecenoic acid and further to cis-9,cis-12-heptadecadienoic acid through elongation, and Δ9 and Δ12 desaturation reactions, respectively. trans-Vaccenic acid (t11-18:1) and trans-12-octadecenoic acid (t12-18:1) were desaturated by the strain through Δ9 desaturation. The products derived from t11-18:1 were identified as the conjugated linoleic acids (CLAs) of cis-9,trans-11-octadecadienoic acid and trans-9,trans-11-octadecadienoic acid. The product derived from t12-18:1 was identified as cis-9,trans-12-octadecadienoic acid. cis-6,cis-9-Octadecadienoic acid was desaturated to cis-6,cis-9,cis-12-octadecatrienoic acid by this strain through Δ12 desaturation. The broad substrate specificity of the elongation, and Δ9 and Δ12 desaturation reactions of the strain is useful for fatty acid biotransformation.
- Ando, Akinori,Ogawa, Jun,Kishino, Shigenobu,Ito, Taiyo,Shirasaka, Norifumi,Sakuradani, Eiji,Yokozeki, Kenzo,Shimizu, Sakayu
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experimental part
p. 227 - 233
(2010/06/16)
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- Polycondensation of naphthalene and its alkyl derivatives
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Polycondensation of naphthalene and its alkyl derivatives (stripping oil, 2,5-dimethylnaphthalene) in the presence of aluminum halides was performed. Under the action of an ultrasonic field on a benzene solution of naphthalene in the presence of the catalyst, intermolecular condensation and benzene addition are observed.
- Golounin,Marakushina,Khramenko
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experimental part
p. 2137 - 2140
(2009/06/05)
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- Process for the preparation of saturated or unsaturated primary fatty amines
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Process for the preparation of unsaturated and saturated primary fatty amines comprising the steps of chlorination, treatment by ammonia, reduction and purification
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Page/Page column 6-7
(2008/06/13)
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- Indium-mediated chemoselective deprotection and demonochlorination of 2,2,2-trichloroethyl esters
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On treatment with indium metal, the 2,2,2-trichloroethyl carboxylates smoothly undergo deprotection to carboxylic acids and reductive demonochlorination to 2,2-dichloroethyl esters, sharply depending on their structures.
- Mineno, Tomoko,Kansui, Hisao,Kunieda, Takehisa
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p. 5027 - 5030
(2008/02/10)
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- Process for separating saturated and unsaturated fatty acids for producing cold-tolorant biodiesel fuel from soy oil
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A process for separating a blend of saturated and unsaturated fatty acids or saturated and unsaturated fatty acid alkyl esters into a first fraction enriched with the saturated fatty acids or saturated fatty acid alkyl esters and a second fraction enriched with unsaturated fatty acids or unsaturated fatty acid alkyl esters. When separating fatty acids, the process includes the steps of (a) saponifying a blend of long chain saturated and unsaturated fatty acids to form free fatty acids, (b) complexing the free fatty acids with urea, and (c) separating the urea complexed free fatty acids into a first fraction enriched with saturated free fatty acids and a second fraction enriched with unsaturated free fatty acids. When separating fatty acid alkyl esters, the process includes the steps of (i) complexing the fatty acid alkyl esters with urea, and (ii) separating the urea complexed fatty acid alkyl esters into a first fraction enriched with saturated fatty acid alkyl esters and a second fraction enriched with unsaturated fatty acid alkyl esters.
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Page/Page column 2-3
(2008/06/13)
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- Copper compositions and their use as hydrogenation catalysts
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Copper compositions that are useful as hydrogenation catalysts are disclosed. In particular, the copper compounds are catalysts for the selective hydrogenation of oils that contain unsaturated fatty acyl components such as unsaturated vegetable oils. Methods of preparing the copper compositions are also disclosed. Methods of hydrogenating unsaturated compositions that contain at least two sites of unsaturation using the hydrogenation catalysts, along with products obtained from the hydrogenation reactions described herein are also disclosed.
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Page/Page column 12
(2008/06/13)
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- Method for preparing unsaturated fatty acids
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Disclosed relates to a method for preparing unsaturated fatty acids and, more particularly, to a method for preparing unsaturated fatty acids in a high purity of at least 99% by isolating and purifying unsaturated fatty acids via a secondary nucleation mechanism using fatty acid-urea inclusion compounds.
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Page/Page column 3; Sheet 2
(2008/06/13)
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- Process
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A process for producing a conjugated di- or poly-unsaturated fatty acid having from 12 to 24 carbon atoms, or a salt or ester thereof, comprises reacting a non-conjugated free fatty acid, or a salt or ester thereof with a base in the presence of a solvent comprising a monohydric alcohol having from 1 to 6 carbon atoms, wherein the reaction is carried out at a temperature of from 120° C. to 200° C. in the presence of water in an amount of at least 4% by weight based on alcohol.
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Page/Page column 4-5
(2008/06/13)
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- An isozyme of earthworm serine proteases acts on hydrolysis of triacylglycerol
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An enzyme catalyzing the hydrolysis of triacylglycerol was purified from an earthworm. The N-terminal amino acid sequence and the catalytic function of the purified enzyme were identical to those of Isozyme C, an isozyme of the earthworm-serine proteases. No other lipase proteins were found in the earthworm cells. The isozyme might act on the hydrolysis of triacylglycerol as well as the protein decomposition.
- Nakajima, Nobuyoshi,Sugimoto, Manabu,Tsuboi, Sadao,Tsuji, Hideaki,Ishihara, Kohji
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p. 2009 - 2011
(2008/02/03)
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- Lipopeptides containing an interferon-γ fragment, and uses thereof in pharmaceutical compositions
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The invention concerns any lipopeptide characterized in that it comprises: a peptide part comprising the peptide sequence consisting of about 30 to about 50 of the last contiguous amino acids of the interferon-γ (IFN-γ) C-terminal end of mammals, whereof, if required, the last 3 to 20 amino acids have been suppressed; and one or several lipophilic parts comprising C4-C20 chain of carbon atoms, saturated or unsaturated, linear or branched, or a steroid group. The invention also concerns any lipopeptide such as defined above containing one or several CD8, and/or CD4, and/or B epitopes. The invention further concerns medicines or vaccines containing any polypeptide such as defined above.
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- Polyepitopic proteinic fragments of the E6 and E7 HPV proteins, production and use thereof in vaccines
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Polyepitopic fragments of the E6 or E7 protein of HPV comprise a peptide sequence of about 15 to 30 amino acids. This peptide sequence contains amino acid sequences of at least 3 different epitopes binding stably to HLA molecules of identical or different type, when these epitopes are obtained by enzymatic degradation of the peptide sequence, particularly in the proteasome, such that at least 4 HLA molecules of different types bind to these epitopes. These 4 HLA molecules are selected from among those of types A1, A2, A3, A11, A24, A29, B7, B8, B18, B27, B35, B44, B51 and B62.
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