Base de dados : MEDLINE
Pesquisa : D02.522.120.100 [Categoria DeCS]
Referências encontradas : 244 [refinar]
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[PMID]:28374446
[Au] Autor:Boonsombat J; Prachyawarakorn V; Pansanit A; Mahidol C; Ruchirawat S; Thongnest S
[Ad] Endereço:Chulabhorn Research Institute, Kamphaeng Phet 6 Road, Bangkok, 10210, Thailand.
[Ti] Título:Superbanone, A New 2-Aryl-3-benzofuranone and Other Bioactive Constituents from the Tube Roots of Butea superba.
[So] Source:Chem Biodivers;14(7), 2017 Jul.
[Is] ISSN:1612-1880
[Cp] País de publicação:Switzerland
[La] Idioma:eng
[Ab] Resumo:Phytochemical investigation from the tube roots of Butea superba, led to the isolation and identification of a new 2-aryl-3-benzofuranone named superbanone (1), one benzoin, 2-hydroxy-1-(2-hydroxy-4-methoxyphenyl)-2-(4-methoxyphenyl)ethanone (2), eight pterocarpans (3 - 10), and eleven isoflavonoids (11 - 21). Compound 2 was identified for the first time as a natural product. The structure of the isolated compounds was elucidated using spectroscopic methods, mainly 1D- and 2D-NMR. The isolated compounds and their derivatives were evaluated for α-glucosidase inhibitory and antimalarial activities. Compounds 3, 7, 8, and 11 showed promising α-glucosidase inhibitory activity (IC  = 13.71 ± 0.54, 23.54 ± 0.75, 28.83 ± 1.02, and 12.35 ± 0.36 µm, respectively). Compounds 3 and 11 were twofold less active than the standard drug acarbose (IC  = 6.54 ± 0.04 µm). None of the tested compounds was found to be active against Plasmodium falciparum strain 94. On the basis of biological activity results, structure-activity relationships are discussed.
[Mh] Termos MeSH primário: Antimaláricos/isolamento & purificação
Benzofuranos/isolamento & purificação
Butea/química
Inibidores de Glicosídeo Hidrolases/isolamento & purificação
[Mh] Termos MeSH secundário: Antimaláricos/química
Antimaláricos/farmacologia
Benzofuranos/farmacologia
Benzoína/isolamento & purificação
Flavonoides/isolamento & purificação
Inibidores de Glicosídeo Hidrolases/química
Inibidores de Glicosídeo Hidrolases/farmacologia
Raízes de Plantas/química
Plasmodium falciparum/efeitos dos fármacos
Pterocarpanos/isolamento & purificação
Relação Estrutura-Atividade
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Antimalarials); 0 (Benzofurans); 0 (Flavonoids); 0 (Glycoside Hydrolase Inhibitors); 0 (Pterocarpans); L7J6A1NE81 (Benzoin)
[Em] Mês de entrada:1709
[Cu] Atualização por classe:170922
[Lr] Data última revisão:
170922
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:170405
[St] Status:MEDLINE
[do] DOI:10.1002/cbdv.201700044


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[PMID]:27040110
[Au] Autor:Hasanpour F; Hadadzadeh H; Taei M; Nekouei M; Mozafari E
[Ad] Endereço:Chemistry Department, Payame Noor University, 19395-4697, Tehran, Iran. F.Hasanpour@pnu.ac.ir.
[Ti] Título:Sensitive spectrophotometric determination of Co(II) using dispersive liquid-liquid micro-extraction method in soil samples.
[So] Source:Environ Monit Assess;188(5):265, 2016 May.
[Is] ISSN:1573-2959
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:Analytical performance of conventional spectrophotometer was developed by coupling of effective dispersive liquid-liquid micro-extraction method with spectrophotometric determination for ultra-trace determination of cobalt. The method was based on the formation of Co(II)-alpha-benzoin oxime complex and its extraction using a dispersive liquid-liquid micro-extraction technique. During the present work, several important variables such as pH, ligand concentration, amount and type of dispersive, and extracting solvent were optimized. It was found that the crucial factor for the Co(II)-alpha benzoin oxime complex formation is the pH of the alkaline alcoholic medium. Under the optimized condition, the calibration graph was linear in the ranges of 1.0-110 µg L(-1) with the detection limit (S/N = 3) of 0.5 µg L(-1). The preconcentration operation of 25 mL of sample gave enhancement factor of 75. The proposed method was applied for determination of Co(II) in soil samples.
[Mh] Termos MeSH primário: Cobalto/análise
Monitoramento Ambiental/métodos
Microextração em Fase Líquida
Poluentes do Solo/análise
Solo/química
[Mh] Termos MeSH secundário: Benzoína/análogos & derivados
Calibragem
Concentração de Íons de Hidrogênio
Limite de Detecção
Oximas
Solventes
Espectrofotometria
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Oximes); 0 (Soil); 0 (Soil Pollutants); 0 (Solvents); 0 (alpha-benzoin oxime); 3G0H8C9362 (Cobalt); L7J6A1NE81 (Benzoin)
[Em] Mês de entrada:1609
[Cu] Atualização por classe:171116
[Lr] Data última revisão:
171116
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160405
[St] Status:MEDLINE
[do] DOI:10.1007/s10661-016-5263-x


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[PMID]:26916231
[Au] Autor:Shirvani G; Shockravi A; Amini M; Saemian N
[Ad] Endereço:Nuclear Science Research School, Nuclear Science and Technology Research Institute, End of North Karegar Ave, 14395-836, Tehran, Iran.
[Ti] Título:Synthesis of 2-(methylsulfonyl)-5-(4-(methylsulfonyl) phenyl)-4-phenyl-1H-[5-(14)C]imidazole, a selective COX-2 inhibitor, via asymmetrical benzoins.
[So] Source:J Labelled Comp Radiopharm;59(4):153-6, 2016 Apr.
[Is] ISSN:1099-1344
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:4,5-Diarylimidazoles labeled with carbon-14 in the 5-position of the imidazole ring were prepared as a part of three-step sequence from 2-hydroxy-1-(4-(methylthio)phenyl)-2-phenyl[1-(14) C]ethanone as a key synthetic intermediate which has been synthesized from potassium [(14) C]cyanide.
[Mh] Termos MeSH primário: Benzoína/química
Inibidores de Ciclo-Oxigenase 2/química
Inibidores de Ciclo-Oxigenase 2/síntese química
Ciclo-Oxigenase 2/metabolismo
Imidazóis/química
Imidazóis/síntese química
Sulfonas/química
Sulfonas/síntese química
[Mh] Termos MeSH secundário: Técnicas de Química Sintética
Desenho de Drogas
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (2-(methylsulfonyl)-5-(4-(methylsulfonyl)phenyl)-4-phenyl-1H-imidazole); 0 (Cyclooxygenase 2 Inhibitors); 0 (Imidazoles); 0 (Sulfones); EC 1.14.99.1 (Cyclooxygenase 2); L7J6A1NE81 (Benzoin)
[Em] Mês de entrada:1701
[Cu] Atualização por classe:170104
[Lr] Data última revisão:
170104
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160227
[St] Status:MEDLINE
[do] DOI:10.1002/jlcr.3382


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[PMID]:26147067
[Au] Autor:Tural S; Tural B; Demir AS
[Ad] Endereço:Department of Chemistry, Faculty of Education, Dicle University, Diyarbakir, Turkey.
[Ti] Título:Heterofunctional Magnetic Metal-Chelate-Epoxy Supports for the Purification and Covalent Immobilization of Benzoylformate Decarboxylase From Pseudomonas Putida and Its Carboligation Reactivity.
[So] Source:Chirality;27(9):635-42, 2015 Sep.
[Is] ISSN:1520-636X
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:In this study, the combined use of the selectivity of metal chelate affinity chromatography with the capacity of epoxy supports to immobilize poly-His-tagged recombinant benzoylformate decarboxylase from Pseudomonas putida (BFD, E.C. 4.1.1.7) via covalent attachment is shown. This was achieved by designing tailor-made magnetic chelate-epoxy supports. In order to selectively adsorb and then covalently immobilize the poly-His-tagged BFD, the epoxy groups (300 µmol epoxy groups/g support) and a very small density of Co(2+)-chelate groups (38 µmol Co(2+)/g support) was introduced onto magnetic supports. That is, it was possible to accomplish, in a simple manner, the purification and covalent immobilization of a histidine-tagged recombinant BFD. The magnetically responsive biocatalyst was tested to catalyze the carboligation reactions. The benzoin condensation reactions were performed with this simple and convenient heterogeneous biocatalyst and were comparable to that of a free-enzyme-catalyzed reaction. The enantiomeric excess (ee) of (R)-benzoin was obtained at 99 ± 2% for the free enzyme and 96 ± 3% for the immobilized enzyme. To test the stability of the covalently immobilized enzyme, the immobilized enzyme was reused in five reaction cycles for the formation of chiral 2-hydroxypropiophenone (2-HPP) from benzaldehyde and acetaldehyde, and it retained 96% of its original activity after five reaction cycles.
[Mh] Termos MeSH primário: Carboxiliases/química
Quelantes/química
Cobalto/química
Enzimas Imobilizadas/química
Compostos de Epóxi/química
Imãs/química
Pseudomonas putida/enzimologia
[Mh] Termos MeSH secundário: Acetaldeído/química
Acetona/análogos & derivados
Acetona/síntese química
Acetona/química
Benzaldeídos/química
Benzoína/química
Biocatálise
Carboxiliases/isolamento & purificação
Carboxiliases/metabolismo
Enzimas Imobilizadas/isolamento & purificação
Enzimas Imobilizadas/metabolismo
Histidina/química
Estereoisomerismo
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Benzaldehydes); 0 (Chelating Agents); 0 (Enzymes, Immobilized); 0 (Epoxy Compounds); 1364PS73AF (Acetone); 26062-48-6 (polyhistidine); 3G0H8C9362 (Cobalt); 4QD397987E (Histidine); 90-63-1 (1-hydroxy-1-phenyl-2-propanone); EC 4.1.1.- (Carboxy-Lyases); EC 4.1.1.7 (benzoylformate decarboxylase); GO1N1ZPR3B (Acetaldehyde); L7J6A1NE81 (Benzoin); TA269SD04T (benzaldehyde)
[Em] Mês de entrada:1605
[Cu] Atualização por classe:150819
[Lr] Data última revisão:
150819
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150707
[St] Status:MEDLINE
[do] DOI:10.1002/chir.22477


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[PMID]:26099539
[Au] Autor:Sabbah DA; Saada M; Khalaf RA; Bardaweel S; Sweidan K; Al-Qirim T; Al-Zughier A; Halim HA; Sheikha GA
[Ad] Endereço:Department of Pharmacy, Faculty of Pharmacy, Al-Zaytoonah University of Jordan, P.O. Box 130, Amman 11733, Jordan. Electronic address: dima_sabbah@yahoo.com.
[Ti] Título:Molecular modeling based approach, synthesis, and cytotoxic activity of novel benzoin derivatives targeting phosphoinostide 3-kinase (PI3Kα).
[So] Source:Bioorg Med Chem Lett;25(16):3120-4, 2015 Aug 15.
[Is] ISSN:1464-3405
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:The oncogenic potential of phosphatidylinositol 3-kinase (PI3Kα) has made it an attractive target for anticancer drug design. In this work, we describe our efforts to optimize the lead PI3Kα inhibitor 2-hydroxy-1,2-diphenylethanone (benzoin). A series of 2-oxo-1,2-diphenylethyl benzoate analogs were identified as potential PI3Kα inhibitors. Docking studies confirmed that the aromatic interaction is mediating ligand/protein complex formation and identified Lys802 and Val851 as H-bonding key residues. Our biological data in human colon carcinoma HCT116 showed that the structure analogs inhibited cell proliferation and induced apoptosis.
[Mh] Termos MeSH primário: Antineoplásicos/síntese química
Benzoína/análogos & derivados
Fosfatidilinositol 3-Quinases/antagonistas & inibidores
Inibidores de Proteínas Quinases/síntese química
[Mh] Termos MeSH secundário: Antineoplásicos/química
Antineoplásicos/farmacologia
Apoptose/efeitos dos fármacos
Benzoína/síntese química
Benzoína/farmacologia
Sítios de Ligação
Proliferação Celular/efeitos dos fármacos
Desenho de Drogas
Células HCT116
Seres Humanos
Simulação de Acoplamento Molecular
Fosfatidilinositol 3-Quinases/metabolismo
Inibidores de Proteínas Quinases/química
Inibidores de Proteínas Quinases/farmacologia
Estrutura Terciária de Proteína
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Antineoplastic Agents); 0 (Protein Kinase Inhibitors); EC 2.7.1.- (Phosphatidylinositol 3-Kinases); L7J6A1NE81 (Benzoin)
[Em] Mês de entrada:1604
[Cu] Atualização por classe:150706
[Lr] Data última revisão:
150706
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150624
[St] Status:MEDLINE


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[PMID]:25850896
[Au] Autor:Lee JH; Jang JH; Velusamy N; Jung HS; Bhuniya S; Kim JS
[Ad] Endereço:Department of Chemistry, Korea University, Seoul 136-701, Korea. jongskim@korea.ac.kr.
[Ti] Título:An intramolecular crossed-benzoin reaction based KCN fluorescent probe in aqueous and biological environments.
[So] Source:Chem Commun (Camb);51(36):7709-12, 2015 May 04.
[Is] ISSN:1364-548X
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:A turn-on fluorescent probe was designed for selective cyanide anion sensing in aqueous and biological environments. The probe underwent an intramolecular crossed-benzoin reaction in the presence of KCN to expel the fluorophore resorufin. This probe was sensitive to KCN concentrations as low as 4 nM in aqueous media.
[Mh] Termos MeSH primário: Benzoína/química
Cianetos/análise
Corantes Fluorescentes/química
Cianeto de Potássio/análise
[Mh] Termos MeSH secundário: Ânions/análise
Células HeLa
Seres Humanos
Microscopia Confocal
Estrutura Molecular
Oxazinas/química
Espectrometria de Fluorescência
Água/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Anions); 0 (Cyanides); 0 (Fluorescent Dyes); 0 (Oxazines); 059QF0KO0R (Water); 635-78-9 (resorufin); L7J6A1NE81 (Benzoin); MQD255M2ZO (Potassium Cyanide)
[Em] Mês de entrada:1602
[Cu] Atualização por classe:150421
[Lr] Data última revisão:
150421
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150409
[St] Status:MEDLINE
[do] DOI:10.1039/c5cc02234g


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[PMID]:25672268
[Au] Autor:Liu T; Han SM; Han LL; Wang L; Cui XY; Du CY; Bi S
[Ad] Endereço:Department of Chemistry and Chemical Engineering, Key Lab of Inorganic Chemistry, Shandong Provincial Education Department, Jining University, Qufu 273155, Shandong, China.
[Ti] Título:Theoretical investigation on the chemoselective N-heterocyclic carbene-catalyzed cross-benzoin reactions.
[So] Source:Org Biomol Chem;13(12):3654-61, 2015 Mar 28.
[Is] ISSN:1477-0539
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:A density functional theory study was performed to understand the detailed mechanisms of the cross-benzoin reactions catalyzed by N-heterocyclic carbene (NHC) species. Our theoretical study predicted that the first H-transfer operates with water in solution as a mediator, and the second H-transfer undergoes a concerted mechanism rather than a stepwise one. In addition, the chemoselectivity of the reactions studied in this work has been explored. P1 was obtained as a major product mainly due to the more stable intermediate formed by reaction of NHC with reactant R1. Different steric effects resulting from the fused six-membered ring in transition state TS7 and the fused five-membered ring in transition state TS13 are the origin leading to the chemoselectivity.
[Mh] Termos MeSH primário: Benzoína/química
Compostos Heterocíclicos/química
Metano/análogos & derivados
Modelos Teóricos
[Mh] Termos MeSH secundário: Catálise
Metano/química
Conformação Molecular
Termodinâmica
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Heterocyclic Compounds); 2465-56-7 (carbene); L7J6A1NE81 (Benzoin); OP0UW79H66 (Methane)
[Em] Mês de entrada:1512
[Cu] Atualização por classe:150312
[Lr] Data última revisão:
150312
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150213
[St] Status:MEDLINE
[do] DOI:10.1039/c4ob02064b


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[PMID]:25640727
[Au] Autor:Hernández K; Parella T; Joglar J; Bujons J; Pohl M; Clapés P
[Ad] Endereço:Biotransformation and Bioactive Molecules Group, Instituto de Química Avanzada de Cataluña, IQAC-CSIC. Jordi Girona 18-26, 08034 Barcelona (Spain), Fax: (+34) 932045904.
[Ti] Título:Expedient synthesis of C-aryl carbohydrates by consecutive biocatalytic benzoin and aldol reactions.
[So] Source:Chemistry;21(8):3335-46, 2015 Feb 16.
[Is] ISSN:1521-3765
[Cp] País de publicação:Germany
[La] Idioma:eng
[Ab] Resumo:The introduction of aromatic residues connected by a C-C bond into the non-reducing end of carbohydrates is highly significant for the development of innovative structures with improved binding affinity and selectivity (e.g., C-aril-sLex). In this work, an expedient asymmetric "de novo" synthetic route to new aryl carbohydrate derivatives based on two sequential stereoselectively biocatalytic carboligation reactions is presented. First, the benzoin reaction of aromatic aldehydes to dimethoxyacetaldehyde is conducted, catalyzed by benzaldehyde lyase from Pseudomonas fluorescens biovar I. Then, the α-hydroxyketones formed are reduced by using NaBH4 yielding the anti diol. After acetal hydrolysis, the aldol addition of dihydroxyacetone, hydroxyacetone, or glycolaldehyde catalyzed by the stereocomplementary D-fructose-6-phosphate aldolase and L-rhamnulose-1-phosphate aldolase is performed. Both aldolases accept unphosphorylated donor substrates, avoiding the need of handling the phosphate group that the dihydroxyacetone phosphate-dependent aldolases require. In this way, 6-C-aryl-L-sorbose, 6-C-aryl-L-fructose, 6-C-aryl-L-tagatose, and 5-C-aryl-L-xylose derivatives are prepared by using this methodology.
[Mh] Termos MeSH primário: Aldeído Liases/química
Aldeídos/química
Benzoína/química
Carboidratos/síntese química
Di-Hidroxiacetona/química
Escherichia coli/química
Frutosefosfatos/síntese química
[Mh] Termos MeSH secundário: Aldeído Liases/metabolismo
Biocatálise
Carboidratos/química
Escherichia coli/metabolismo
Frutosefosfatos/química
Estrutura Molecular
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Aldehydes); 0 (Carbohydrates); 0 (Fructosephosphates); 6814-87-5 (fructose-6-phosphate); EC 4.1.2.- (Aldehyde-Lyases); EC 4.1.2.- (benzaldehyde lyase); EC 4.1.2.19 (rhamnulose-1-phosphate adolase); L7J6A1NE81 (Benzoin); O10DDW6JOO (Dihydroxyacetone)
[Em] Mês de entrada:1605
[Cu] Atualização por classe:150206
[Lr] Data última revisão:
150206
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150203
[St] Status:MEDLINE
[do] DOI:10.1002/chem.201406156


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[PMID]:25033237
[Au] Autor:Alamgir M; Khuhawar MY; Memon SQ; Hayat A; Zounr RA
[Ad] Endereço:Institute of Advance Research Studies in Chemical Sciences, University of Sindh, Jamshoro, Pakistan. Electronic address: aalam012@gmail.com.
[Ti] Título:Spectrofluorimetric analysis of famotidine in pharmaceutical preparations and biological fluids by derivatization with benzoin.
[So] Source:Spectrochim Acta A Mol Biomol Spectrosc;134:449-52, 2015 Jan 05.
[Is] ISSN:1873-3557
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:A sensitive and simple spectrofluorimetric method has been developed for the analysis of famotidine, from pharmaceutical preparations and biological fluids after derivatization with benzoin. The reaction was carried out in alkaline medium with measurement of fluorescence intensity at 446 nm with excitation wavelength at 286 nm. Linear calibration was obtained with 0.5-15 µg/ml with coefficient of determination (r(2)) 0.997. The factors affecting the fluorescence intensity were optimized. The pharmaceutical additives and amino acid did not interfere in the determination. The mean percentage recovery (n=4) calculated by standard addition from pharmaceutical preparation was 94.8-98.2% with relative standard deviation (RSD) 1.56-3.34% and recovery from deproteinized spiked serum and urine of healthy volunteers was 98.6-98.9% and 98.0-98.4% with RSD 0.34-0.84% and 0.29-0.87% respectively.
[Mh] Termos MeSH primário: Benzoína/química
Famotidina/sangue
Famotidina/urina
Antagonistas dos Receptores Histamínicos H2/sangue
Antagonistas dos Receptores Histamínicos H2/urina
[Mh] Termos MeSH secundário: Famotidina/análise
Antagonistas dos Receptores Histamínicos H2/análise
Seres Humanos
Limite de Detecção
Espectrometria de Fluorescência/métodos
[Pt] Tipo de publicação:EVALUATION STUDIES; JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Histamine H2 Antagonists); 5QZO15J2Z8 (Famotidine); L7J6A1NE81 (Benzoin)
[Em] Mês de entrada:1507
[Cu] Atualização por classe:140830
[Lr] Data última revisão:
140830
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:140718
[St] Status:MEDLINE


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[PMID]:25382418
[Au] Autor:Loschonsky S; Wacker T; Waltzer S; Giovannini PP; McLeish MJ; Andrade SL; Müller M
[Ad] Endereço:Institute of Pharmaceutical Sciences, Albert-Ludwigs-Universität Freiburg, Albertstrasse 25, 79104 Freiburg (Germany).
[Ti] Título:Extended reaction scope of thiamine diphosphate dependent cyclohexane-1,2-dione hydrolase: from C-C bond cleavage to C-C bond ligation.
[So] Source:Angew Chem Int Ed Engl;53(52):14402-6, 2014 Dec 22.
[Is] ISSN:1521-3773
[Cp] País de publicação:Germany
[La] Idioma:eng
[Ab] Resumo:ThDP-dependent cyclohexane-1,2-dione hydrolase (CDH) catalyzes the CC bond cleavage of cyclohexane-1,2-dione to 6-oxohexanoate, and the asymmetric benzoin condensation between benzaldehyde and pyruvate. One of the two reactivities of CDH was selectively knocked down by mutation experiments. CDH-H28A is much less able to catalyze the CC bond formation, while the ability for CC bond cleavage is still intact. The double variant CDH-H28A/N484A shows the opposite behavior and catalyzes the addition of pyruvate to cyclohexane-1,2-dione, resulting in the formation of a tertiary alcohol. Several acyloins of tertiary alcohols are formed with 54-94 % enantiomeric excess. In addition to pyruvate, methyl pyruvate and butane-2,3-dione are alternative donor substrates for CC bond formation. Thus, the very rare aldehyde-ketone cross-benzoin reaction has been solved by design of an enzyme variant.
[Mh] Termos MeSH primário: Hidrolases/metabolismo
Tiamina Pirofosfato/química
[Mh] Termos MeSH secundário: Substituição de Aminoácidos
Azoarcus/enzimologia
Benzoína/química
Biocatálise
Carbono/química
Domínio Catalítico
Cicloexanonas/química
Cicloexanonas/metabolismo
Hidrolases/química
Hidrolases/genética
Ácido Pirúvico/química
Ácido Pirúvico/metabolismo
Tiamina Pirofosfato/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Cyclohexanones); 7440-44-0 (Carbon); 75C1OVW0FJ (1,2-cyclohexanedione); 8558G7RUTR (Pyruvic Acid); EC 3.- (Hydrolases); L7J6A1NE81 (Benzoin); Q57971654Y (Thiamine Pyrophosphate)
[Em] Mês de entrada:1508
[Cu] Atualização por classe:171116
[Lr] Data última revisão:
171116
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:141111
[St] Status:MEDLINE
[do] DOI:10.1002/anie.201408287



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