- PHOTOINITIATORS FOR LIGHT-CURABLE COMPOSITIONS
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Compounds of formula (I) are photoinitiators or photosensitizers in a photopolymerizable composition: R1 represents a monovalent, linear, branched or cyclic, aliphatic hydrocarbon group having 1 to 20 carbon atoms, optionally substituted with substituent(s) selected from —Cl, —Br, —OH, ═O, —NH—CO— OR2, —NH—CO—R2 or free-radically or ionically polymerizable groups. Each R2 is independently —H or C1-6 alkyl; n is ≥1. If n=1, Z and Y are absent and X represents —OR3; if n is >1, Z represents —OR4—, Y represents —ORs— and X represents —H or —OH. R3 represents —H or R1; and R4 and R5 each independently represent a bivalent hydrocarbon group. The polymerizable moieties as optional substituents of R1 are polymerizable double or triple bonds, lactam, lactone and epoxide moieties, which are subjectable to ring-opening polymerization; and two of R1 to R5 may be linked to one another to form a ring or a dimer.
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Paragraph 0069-0072
(2020/08/05)
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- Simultaneous monitoring of the bioconversion from lysine to glutaric acid by ethyl chloroformate derivatization and gas chromatography-mass spectrometry
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Glutaric acid is a precursor of a plasticizer that can be used for the production of polyester amides, ester plasticizer, corrosion inhibitor, and others. Glutaric acid can be produced either via bioconversion or chemical synthesis, and some metabolites and intermediates are produced during the reaction. To ensure reaction efficiency, the substrates, intermediates, and products, especially in the bioconversion system, should be closely monitored. Until now, high performance liquid chromatography (HPLC) has generally been used to analyze the glutaric acid-related metabolites, although it demands separate time-consuming derivatization and non-derivatization analyses. To substitute for this unreasonable analytical method, we applied herein a gas chromatography - mass spectrometry (GC-MS) method with ethyl chloroformate (ECF) derivatization to simultaneously monitor the major metabolites. We determined the suitability of GC-MS analysis using defined concentrations of six metabolites (L-lysine, cadaverine, 5-aminovaleric acid, 2-oxoglutaric acid, glutamate, and glutaric acid) and their mass chromatograms, regression equations, regression coefficient values (R2), dynamic ranges (mM), and retention times (RT). This method successfully monitored the production process in complex fermentation broth.
- Bhatia, Shashi Kant,Choi, Tae-Rim,Choi, Yong-Keun,Gurav, Ranjit,Han, Yeong-Hoon,Kim, Hyun-Joong,Kim, Wooseong,Park, Kyungmoon,Park, See-Hyoung,Park, Ye-Lim,Song, Hun-Suk,Yang, Yung-Hun
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- Preparation method of 2- diethyl-1,5- n-pentanedioic acid diethyl ester (by machine translation)
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The reaction liquid is mixed uniformly, 2 - and then the reaction solution is stirred and reacted at a normal temperature, and the reaction solution Amberlyst - 15 is filtered 2 - 2 - and concentrated to obtain diethyl-ethyl-diformate 2 - 15:1~1.2 Amberlyst - 15 2 - 1:2~2.2. The preparation method is mild in reaction condition, safe and simple in preparation process and purification steps, high in product yield and convenient to realize industrialization. (by machine translation)
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Paragraph 0010-0022
(2019/12/02)
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- Biotechnological properties of sponges from northeast Brazil: Cliona varians as a Biocatalyst for Enantioselective Reduction of Carbonyl Compounds
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To research the potential ability of whole marine sponges to act as biocatalysts, this paper describes for the first time the employment of whole Cliona varians sponge in the stereoselective reduction of prochiral α-keto esters and isatin to the corresponding chiral alcohols. The addition of D-fructose, D-glucose or sucrose remarkably increased the conversion ratios and stereoselectivities by this marine sponge. Furthermore, in the presence of D-glucose and D-maltose, the reduction of isatin by C. varians afforded the corresponding 3-hydroxyindolin-2-one with high conversions (85-90percent) and good enantioselectivities (60-74percent). These results showed that the marine sponge presents great potential to be used as biocatalyst for stereoselective reduction of carbonyl compounds.
- Riatto, Valéria B.,Victor, Mauricio M.,Sousa, Jaqueline F.,Menegola, Carla
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p. 149 - 157
(2018/12/13)
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- Identification and Structure-Activity Relationship of HDAC6 Zinc-Finger Ubiquitin Binding Domain Inhibitors
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HDAC6 plays a central role in the recruitment of protein aggregates for lysosomal degradation and is a promising target for combination therapy with proteasome inhibitors in multiple myeloma. Pharmacologically displacing ubiquitin from the zinc-finger ubiquitin-binding domain (ZnF-UBD) of HDAC6 is an underexplored alternative to catalytic inhibition. Here, we present the discovery of an HDAC6 ZnF-UBD-focused chemical series and its progression from virtual screening hits to low micromolar inhibitors. A carboxylate mimicking the C-terminal extremity of ubiquitin, and an extended aromatic system stacking with W1182 and R1155, are necessary for activity. One of the compounds induced a conformational remodeling of the binding site where the primary binding pocket opens up onto a ligand-able secondary pocket that may be exploited to increase potency. The preliminary structure-activity relationship accompanied by nine crystal structures should enable further optimization into a chemical probe to investigate the merit of targeting the ZnF-UBD of HDAC6 in multiple myeloma and other diseases.
- Ferreira De Freitas, Renato,Harding, Rachel J.,Franzoni, Ivan,Ravichandran, Mani,Mann, Mandeep K.,Ouyang, Hui,Lautens, Mark,Santhakumar, Vijayaratnam,Arrowsmith, Cheryl H.,Schapira, Matthieu
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supporting information
p. 4517 - 4527
(2018/05/31)
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- Small Molecule Antagonists of the Interaction between the Histone Deacetylase 6 Zinc-Finger Domain and Ubiquitin
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Inhibitors of HDAC6 have attractive potential in numerous cancers. HDAC6 inhibitors to date target the catalytic domains, but targeting the unique zinc-finger ubiquitin-binding domain (Zf-UBD) of HDAC6 may be an attractive alternative strategy. We developed X-ray crystallography and biophysical assays to identify and characterize small molecules capable of binding to the Zf-UBD and competing with ubiquitin binding. Our results revealed two adjacent ligand-able pockets of HDAC6 Zf-UBD and the first functional ligands for this domain.
- Harding, Rachel J.,Ferreira De Freitas, Renato,Collins, Patrick,Franzoni, Ivan,Ravichandran, Mani,Ouyang, Hui,Juarez-Ornelas, Kevin A.,Lautens, Mark,Schapira, Matthieu,Von Delft, Frank,Santhakumar, Vjayaratnam,Arrowsmith, Cheryl H.
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supporting information
p. 9090 - 9096
(2017/11/14)
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- Synthesis of quinoline dicarboxylic esters as biocompatible fluorescent tags
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A series of dicarboxylic quinoline derivatives bearing electron-releasing or -withdrawing substituents have been synthesized using mono- or/and biphasic methodologies. By controlling the regioselectivity of addition into our electrophilic intermediate, we also characterized by which mechanism the Doebner-Miller cyclization step occurred. As anticipated, electronreleasing substituents induce a red shift of the low-energy absorption allowing excitation in the visible region. In addition, by playing on the strength and position of the electron-releasing substituents, chromophore having interesting fluorescent properties such as large Stoke shifts, good fluorescent quantum yields, emission in the visible green-yellow region and reasonable two-photon absorption in the NIR region have been obtained. These small-size fluorophores, which can be made water-soluble and have been shown to be non-toxic, can be hetero- and/or polyfunctionalized and thus represent promising key units for fluorescence-based physiological experiments with low background interactions.
- Laras, Younes,Acher, Francine C.,Pietrancosta, Nicolas,Hugues, Vincent,Chandrasekaran, Yogesh,Blanchard-Desce, Mireille
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p. 8294 - 8302,9
(2020/10/15)
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- Radical alkylations of alkyl halides and unactivated C-H bonds using vinyl triflates
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Radical alkylations of activated alkyl iodides and bromides were achieved using vinyl triflates in the presence of hexadimethyltin, whereas those of unactivated C-H bonds using vinyl triflates proceeded cleanly under tin-free conditions. Georg Thieme Verl
- Lee, Jin Young,Lim, Kyoung-Chan,Meng, Xiangjian,Kim, Sunggak
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experimental part
p. 1647 - 1650
(2010/09/04)
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- Expeditious biomimetically-inspired approaches to racemic homocitric acid lactone and per-homocitrate
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Two concise and flexible biomimetically-inspired approaches to homocitric acid lactone (3) and its higher homolog, triethyl per-homocitrate (12), are presented herein. The key steps include an efficient indium metal-mediated allylation-oxidative cleavage procedure and a one-step ethoxycarbonylmethylation of α-oxo-diesters.
- Chen, Hong-Bin,Chen, Ling-Yan,Huang, Pei-Qiang,Zhang, Hong-Kui,Zhou, Zhao-Hui,Tsai, Khi-Rui
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p. 2148 - 2152
(2007/10/03)
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- Efficient synthesis of 1-azadienes derived from α-aminoesters. Regioselective preparation of α-dehydroamino acids, vinylglycines, and α-amino acids
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(Chemical Equation Presented) An efficient synthesis of 1-azadienes derived from α-aminoesters is achieved through an aza-Wittig reaction of phosphazenes with β,γ-unsaturated α-ketoesters. Regioselective 1,2-reduction of these functionalized 1-azadienes affords vinylglycine derivatives, while conjugative 1,4-reduction gives α-dehydroamino acid compounds. Reduction of both the carbon-carbon and the imine-carbon-nitrogen double bonds leads to the formation of α-amino acid derivatives.
- Palacios, Francisco,Vicario, Javier,Aparicio, Domitila
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p. 7690 - 7696
(2007/10/03)
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- Radical alkylation of bis(silyloxy)enamine derivatives of organic nitro compounds
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(Chemical Equation Presented) Alkylation β to a nitro group by radical chemistry is made possible by initial conversion of the organic nitro compound into a bis(silyloxy)enamine (see scheme; TBSOTf=tert-butyldimethylsilyl trifluoromethanesulfonate). An advantage of the method is the simultaneous conversion of the nitro group into a synthetically useful oxime ether group.
- Jin, Young Lee,Hong, Young-Taek,Kim, Sunggak
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p. 6182 - 6186
(2007/10/03)
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- Combination strategy using pure enzymes and whole cells as biocatalysts for the preparation of 2-hydroxyesters and lactones from 2-oxoglutaric acid
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An innovative combination strategy that uses pure enzymes and whole microbial cells in the same process was used to prepare enantiomerically pure 3-carboxyalkyl-γ-butyrolactones and several alkyl esters of 2-hydroxyglutarate from 2-oxoglutaric acid. An innovative combination strategy that uses pure enzymes and whole microbial cells in the same process was used to prepare enantiomerically pure 3-carboxyalkyl-γ-butyrolactones and several alkyl esters of 2-hydroxyglutarates from 2-oxoglutaric acid. The method involves two consecutive biocatalytic steps. The first step, which converts the 2-oxoglutaric acid into the corresponding dialkyl esters, was catalyzed by a lipase. Then in the second step, by microbial reduction of the dialkyl-2-oxoglutarates, it is possible to obtain 3-carboxyalkyl-γ- butyrolactones or 2-hydroxyesters depending on the length of the chain in the alkyl moiety of the esters and on the fresh or lyophilized status of the cells.
- Rustoy, Eduardo M.,Pereyra, Elba N.,Moreno, Silvia,Baldessari, Alicia
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p. 3763 - 3768
(2007/10/03)
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- Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters from dialkyl 2-oxoglutarates
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Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters can be prepared either by enzymatic resolution of the racemic γ-lactones themselves or by bioreduction with baker's yeast of dialkyl 2-oxoglutarates and subsequent cyclization of the resulting dialkyl 2-hydroxyglutarates. The best results were obtained by the former route, by which the desired compounds were isolated in high enantiomeric excess. Bioreductions were less satisfactory. In fact the hydroxyester intermediates were initially formed as racemic mixtures and their final enantiomeric enrichment was reached by asymmetric destruction, occurring in the bioreaction medium, however at the same time large amounts of alkyl 4-hydroxybutanoates were formed as side products.
- Drioli, Sara,Nitti, Patrizia,Pitacco, Giuliana,Tossut, Laura,Valentin, Ennio
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p. 2713 - 2728
(2007/10/03)
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- Oxidation of hydrazones by hypervalent organoiodine reagents: Regeneration of the carbonyl group and facile syntheses of α-acetoxy and α-alkoxy azo compounds
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Various hydrazone derivatives of α-keto esters were prepared. The carbonyl group was readily regenerated in high yield from phenylhydrazones through oxidative hydrolysis using hypervalent organoiodine(III) reagents either bis(trifluoroacetoxy)-iodobenzene (BTIB) in aqueous acetonitrile or hydroxy(tosyloxy)iodobenzene (HTIB) in chloroform. α-Acotxy phenyl- or methylazo compounds were readily synthesized by oxidation of the corresponding hydrazones with iodobenzene diacetate (IBDA) in dichloromethane or acetic acid. α-Methoxy phenyl- or methylazo compounds were also prepared by oxidation of the hydrazones in methanol. The mechanisms of the oxidation reactions are discussed.
- Barton, Derek H. R.,Jaszberenyi, Joseph Cs.,Liu, Wansheng,Shinada, Tetsuro
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p. 14673 - 14688
(2007/10/03)
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- 7-fused 2-(piperazinoalkyl) indole derivatives, intermediates and compositions thereof
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Pharmacologically active compounds having anti-allergic properties corresponding to the formula I STR1 which can be mono- or disubstituted in the phenyl ring and their acid addition salts and/or S-mono- or dioxides of sulfur-containing compounds of the formula I are described, together with processes and intermediates for their preparation.
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- Oxidation of phenylhydrazones of α-keto esters with hypervalent organoiodine reagents
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α-Ketoacids and ketones can easily be regenerated in high yield from their phenylhydrazones via hydroxy azo compounds upon oxidation with hupervalent iodine reagents.
- Barton, Derek H. R.,Jaszberenyi, Joseph Cs.,Shinada, Tetsuro
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p. 7191 - 7194
(2007/10/02)
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- Chemo-enzymatic synthesis of specifically stable-isotope labelled L-glutamic acid and 2-oxoglutaric acid
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(3-13C)-(4-13C)-,(5-13C)- and (3,4-13C2)-2-oxoglutaric acid were prepared starting from the simple 13C-enriched compounds: ethyl bromoacetate and paraformaldehyde, via a single reaction scheme on the gram scale in high yield.This reaction scheme allows specific 13C enrichment of every carbon position and any combination of positions. (3-13C)-,(4-13C)-, (5-13C), (3,4-13C2) and (15N)-L-glutamic acid were prepared by converting the corresponding 2-oxoglutaric acids via an enantioselective enzymatic conversion.The labelled L-glutamic acids and 2-oxoglutaric acids were characterized by 1H NMR, 13C NMR and mass spectrometry.
- Cappon, J. J.,Baart, J.,Walle, G. A. M. van der,Raap, J.,Lugtenburg, J.
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p. 158 - 166
(2007/10/02)
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- Meerwein Reduction of Levulinic Acid Derivatives: A New Route for the Synthesis of Glutamic Acid
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Glutamic acid has been prepared from levulinic acid by a new route.In this method α-ketoglutaric (III) acid is obtained by oxidation of δ-benzallevulinic acid (II) and converted into diethyl ester (IV) which on Meerwein-Pondorff-Verley reduction furnishes the hydroxy derivative (V).The latter (V) is converted into chloro derivative (VI) which on amination gives glutamic acid (VII) in a good yield.Meerwein-Pondorff-Verley reduction of ethyl levulinate, ethyl β-bromolevulinate and 2,7-octanedione has also been studied.However, such a reduction of ethyl β-aminolevulinate remains unsuccessfull.
- Joshi, Uday R.,Limaye, P. A.
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p. 1176 - 1178
(2007/10/02)
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- Synthesis and Properties of Some 7-Dimethylamino-1,4-benzoxazin-2-ones
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The synthesis of the 7-dimethylamino-1,4-benzoxazin-2-ones (5), fluorescent dyes, by condensing α-ketoacids with 2-amino-5-dimethylaminophenol is described.When the 3-substituent is a methyl group, these compounds can be further condensed with aromatic aldehydes to provide the styryl dyes (6).These products are easily opened by hydrochloric acid in ethanolic solution to afford the corresponding benzalketoacid ethyl esters (7).
- Bris, Marie-Therese
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p. 1275 - 1280
(2007/10/02)
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