- Vicinal Diamines as Smart Cosubstrates in the Transaminase-Catalyzed Asymmetric Amination of Ketones
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Transaminases (TAs) have recently been established as catalysts for the asymmetric, reductive amination of prochiral ketones. Depending on the ketone substrate and the amine donor (the cosubstrate), equilibrium constants may limit high conversions; thus, methods to overcome this limitation are required. Removal of the co-product from the reaction equilibrium through spontaneous, intramolecular reactions has provided a successful solution to this problem; therefore, these amine donors have been named “smart cosubstrates”. Here, we present a comparison of various bifunctional amine donors including vicinal diamines as potential structural cosubstrate motifs. Upon TA-catalyzed deamination of 1,2-diamines, spontaneous dimerization of the resulting α-aminoketones and oxidation gave heteroaromatic pyrazines.
- Payer, Stefan E.,Schrittwieser, Joerg H.,Kroutil, Wolfgang
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supporting information
p. 2553 - 2559
(2017/05/12)
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- A (different) bright ammonia amide carbamate derivative and application thereof (by machine translation)
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The invention belongs to the field of plant, relates to a general formula (I) is shown in a (different) bright ammonia amide carbamate derivatives and their pharmaceutically acceptable salt, wherein substituent R has the definition given in the specification, the invention also relates to the general formula (I) preparation of compounds of the, specifically for the preparation of the intermediate of its development and application of plant disease control. (by machine translation)
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Paragraph 0071; 0072
(2017/07/14)
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- (R)- SELECTIVE AMINATION
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The present invention relates to a method for the enzymatic synthesis of enantiomerically enriched (R)-amines of general formula [1][c] from the corresponding ketones of the general formula [1][a] by using novel transaminases. These novel transaminases are selected from two different groups: either from a group of some 20 proteins with sequences as specified herein, or from a group of proteins having transaminase activity and isolated from a microorganism selected from the group of organisms consisting of Rahnella aquatilis, Ochrobactrum anthropi, Ochrobactrum tritici, Sinorhizobium morelense, Curtobacterium pusiffium, Paecilomyces lilacinus, Microbacterium ginsengisoli, Microbacterium trichothecenolyticum, Pseudomonas citronellolis, Yersinia kristensenii, Achromobacter spanius, Achromobacter insolitus, Mycobacterium fortuitum, Mycobacterium frederiksbergense, Mycobacterium sacrum, Mycobacterium fluoranthenivorans, Burkhoideria sp., Burkhoideria tropica, Cosmospora episphaeria, and Fusarium oxysporum.
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Paragraph 0127 - 0132
(2016/03/22)
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- Design, synthesis and effect of the introduction of a propargyloxy group on the fungicidal activities of 1-substituted phenoxypropan-2-amino valinamide carbamate derivatives
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The cell walls of oomycetes are composed of cellulose, making cellulose synthase enzymes good targets for carboxylic acid amide fungicides. Valinamide carbamates are amino acid fungicides that represent excellent alternatives to conventional synthetic pesticides in terms of their ability to reduce the negative impacts of these compounds on human health and the environment. In a continuation of our research towards the development of new cellulose synthase inhibitors, we have developed a series of "stretched" analogues of iprovalicarb by the introduction of an additional OCH2 linker. The bioassay results indicated that compounds containing a small group at the para-position of phenyl gave excellent fungicidal activities with EC50 values ranging from 0.59 to 2.06 μmol L-1. Most notably, the introduction of a propargyloxy group led to a pronounced increase in the fungicidal activity. Furthermore, compound 7o bearing a propargyloxy group was identified as the most promising candidate because of its excellent fungicidal potency against oomycete diseases and good fungicidal activity against non-oomycete diseases.
- Li, Jian-Qiang,Wang, Zhi-Peng,Gao, Yang,Zhao, Wei-Guang
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p. 82131 - 82137
(2016/09/09)
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- CATALYST COMPOUNDS
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The present invention relates to an iridium-based catalyst compound for hydrogenating reducible moieties, especially imines and iminiums, the catalyst compounds being defined by the formulas: where ring B is either itself polycyclic, or ring B together with R is polycyclic. The catalysts of the invention are particularly effective in reductive amination procedures 10 which involve the in situ generation of the imine or iminium under reductive hydrogenative conditions.
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Paragraph 0314; 0323
(2015/03/28)
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- Primary amines by transfer hydrogenative reductive amination of ketones by using cyclometalated IrIII catalysts
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Cyclometalated iridium complexes are found to be versatile catalysts for the direct reductive amination (DRA) of carbonyls to give primary amines under transfer-hydrogenation conditions with ammonium formate as both the nitrogen and hydrogen source. These complexes are easy to synthesise and their ligands can be easily tuned. The activity and chemoselectivity of the catalyst towards primary amines is excellent, with a substrate to catalyst ratio (S/C) of 1000 being feasible. Both aromatic and aliphatic primary amines were obtained in high yields. Moreover, a first example of homogeneously catalysed transfer-hydrogenative DRA has been realised for β-keto ethers, leading to the corresponding β-amino ethers. In addition, non-natural α-amino acids could also be obtained in excellent yields with this method. Reduce the work! A broad range of ketones have been successfully aminated to afford primary amines under transfer-hydrogenation conditions by using ammonium formate as the amine source and 0.1 mol % of a cyclometalated IrIII catalyst (see scheme). Copyright
- Talwar, Dinesh,Salguero, Noemi Poyatos,Robertson, Craig M.,Xiao, Jianliang
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supporting information
p. 245 - 252
(2014/01/17)
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- CATALYST COMPOUNDS
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The present invention relates to an iridium-based catalyst compound for hydrogenating reducible moieties, especially imines and iminiums, the catalyst compounds being defined by the formulas: where ring B is either itself polycyclic, or ring B together with R is polycyclic. The catalysts of the invention are particularly effective in reductive amination procedures 10 which involve the in situ generation of the imine or iminium under reductive hydrogenative conditions.
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Paragraph 00163; 00172
(2013/11/05)
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- Design, synthesis, and pharmacological effects of structurally simple ligands for MT1 and MT2 melatonin receptors
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A series of phenoxyalkyl and phenylthioalkyl amides were prepared as melatoninergic ligands. Modulation of affinity of the newly synthesized compound by applying SARs around the terminal amide moiety, the alkyl chain, and the methoxy group on the aromatic ring provides compounds with nanomolar affinity for both melatonin receptor subtypes. Affinity towards MT1 and MT2 receptors were modulated also exploiting chirality. The investigation of intrinsic activity revealed that all the tested compounds behave as full or partial agonists.
- Carocci, Alessia,Catalano, Alessia,Lovece, Angelo,Lentini, Giovanni,Duranti, Andrea,Lucini, Valeria,Pannacci, Marilou,Scaglione, Francesco,Franchini, Carlo
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experimental part
p. 6496 - 6511
(2010/10/02)
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- Efficient conversion of primary and secondary alcohols to primary amines
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A convenient single-vessel conversion of primary and secondary alcohols to primary amines is reported. Use of this method results in substantially cleaner crude products than similar procedures reported in the literature. A simple work-up also makes this procedure ideal for parallel synthesis.
- Sun, Weilin,Pelletier, Jeffrey C.
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p. 7745 - 7746
(2008/02/12)
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- Design of scytalone dehydratase inhibitors as rice blast fungicides: (N- phenoxypropyl)-carboxamides
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Insights gained from a crystal structure of scytalone dehydratase led to the design of carboxamide inhibitors with a phenoxypropyl group substituted on the nitrogen atom. Potent enzyme inhibitors were synthesized around this motif, the best of which provided excellent control of rice blast disease in greenhouse assays and outdoor field trials.
- Jordan, Douglas B.,Lessen, Thomas A.,Wawrzak, Zdzislaw,Bisaha, John J.,Gehret, Troy C.,Hansen, Stephen L.,Schwartz, Rand S.,Basarab, Gregory S.
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p. 1607 - 1612
(2007/10/03)
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- Novel applications of Raney nickel/isopropanol: Efficient system for the reduction of organic compounds
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Catalytic hydrogenation of various organic substrates with Raney nickle in isopropanol proceeds under mild conditions of temperature and pressure. Comparison with other catalysts systems evidenced the superiority of Raney nickel/isopropanol.
- Regla, Ignacio,Reyes, Adelfo,Koerber, Claudia,Demare, Patricia,Estrada, Osvaldo,Juaristi, Eusebio
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p. 817 - 823
(2007/10/03)
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- Derivatives related to betaxolol with α- and β-adrenergic activities
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The paper describes the synthesis and the pharmacological evaluation of some derivatives of betaxolol, all with an N-aralkylamine instead of the tertiobutylamine. These compounds have been tested for β1-adrenergic receptor antagonism on guinea pig atria, β2-adrenergic receptor antagonism on guinea pig trachea and α-adrenergic blocking activity on rat aorta. Compound U12 with a marked α-blocking activity and compound R8 with a β1/α ratio = 1 were selected for a haemodynamic study in the dog. The decrease in cardiac work and the diminution of total peripheral resistance exhibited by U12 are consistent with a dual α/β-blocking agent. Finally, structure-activity relationships are discussed.
- Leclerc,Decker,Schwartz
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p. 1357 - 1367
(2007/10/02)
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