Base de dados : MEDLINE
Pesquisa : D09.973 [Categoria DeCS]
Referências encontradas : 22 [refinar]
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  1 / 22 MEDLINE  
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[PMID]:26813028
[Au] Autor:Jackson DR; Yu X; Wang G; Patel AB; Calveras J; Barajas JF; Sasaki E; Metsä-Ketelä M; Liu HW; Rohr J; Tsai SC
[Ad] Endereço:Department of Molecular Biology and Biochemistry, Department of Chemistry, and Department of Pharmaceutical Sciences, University of California , Irvine, California 92697, United States.
[Ti] Título:Insights into Complex Oxidation during BE-7585A Biosynthesis: Structural Determination and Analysis of the Polyketide Monooxygenase BexE.
[So] Source:ACS Chem Biol;11(4):1137-47, 2016 Apr 15.
[Is] ISSN:1554-8937
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Cores of aromatic polyketides are essential for their biological activities. Most type II polyketide synthases (PKSs) biosynthesize these core structures involving the minimal PKS, a PKS-associated ketoreductase (KR) and aromatases/cyclases (ARO/CYCs). Oxygenases (OXYs) are rarely involved. BE-7585A is an anticancer polyketide with an angucyclic core. (13)C isotope labeling experiments suggest that its angucyclic core may arise from an oxidative rearrangement of a linear anthracyclinone. Here, we present the crystal structure and functional analysis of BexE, the oxygenase proposed to catalyze this key oxidative rearrangement step that generates the angucyclinone framework. Biochemical assays using various linear anthracyclinone model compounds combined with docking simulations narrowed down the substrate of BexE to be an immediate precursor of aklaviketone, possibly 12-deoxy-aklaviketone. The structural analysis, docking simulations, and biochemical assays provide insights into the role of BexE in BE-7585A biosynthesis and lay the groundwork for engineering such framework-modifying enzymes in type II PKSs.
[Mh] Termos MeSH primário: Policetídeo Sintases/metabolismo
Tioaçúcares/metabolismo
[Mh] Termos MeSH secundário: Conformação Molecular
Oxirredução
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, N.I.H., EXTRAMURAL; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (BE-7585A); 0 (Thiosugars); 79956-01-7 (Polyketide Synthases)
[Em] Mês de entrada:1612
[Cu] Atualização por classe:170415
[Lr] Data última revisão:
170415
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:160128
[St] Status:MEDLINE
[do] DOI:10.1021/acschembio.5b00913


  2 / 22 MEDLINE  
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[PMID]:26260238
[Au] Autor:Tamura Y; Miyagawa H; Yoshida T; Chuman H
[Ad] Endereço:Chemistry Laboratories, Taisho Pharmaceutical Co. Ltd., 1-403 Yoshino-cho, Kita-ku, Saitama-shi, Saitama 331-9530, Japan.
[Ti] Título:Binding interaction of SGLT with sugar and thiosugar by the molecular dynamics simulation.
[So] Source:Biochim Biophys Acta;1848(11 Pt A):2799-804, 2015 Nov.
[Is] ISSN:0006-3002
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:The human sodium-glucose co-transporter 2 (hSGLT2) is a transporter responsible for reabsorption of glucose in the proximal convoluted tubule of the kidney. hSGLT2 inhibitors, including luseogliflozin, have been developed as drugs for type 2 diabetes mellitus. Only luseogliflozin contains a thiosugar ring in its chemical structure, while other hSGLT2 inhibitors contain glucose rings. Consequently, we focused on the binding interactions of hSGLT2 with sugars and thiosugars. We first revealed that the binding affinities of thiosugars are stronger than those of sugars through molecular dynamics simulations of Vibrio parahaemolyticus, sodium-galactose co-transporter, and human hSGLT2. We then demonstrated that Na(+) dissociates from the protein to the cytoplasmic solution more slowly in the thiosugar system than in the sugar system. These differences between sugars and thiosugars are discussed on the basis of the different binding modes due to the atom at the 5-position of the sugar and thiosugar rings. Finally, as a result of Na(+) dissociation, we suggest that the dissociation of thiosugars is slower than that of sugars.
[Mh] Termos MeSH primário: Galactose/química
Glucose/química
Simulação de Dinâmica Molecular
Transportador 2 de Glucose-Sódio/química
Tioaçúcares/química
[Mh] Termos MeSH secundário: Proteínas de Bactérias/química
Proteínas de Bactérias/metabolismo
Sítios de Ligação
Ligação Competitiva
Galactose/metabolismo
Glucose/metabolismo
Seres Humanos
Cinética
Estrutura Molecular
Análise de Componente Principal
Ligação Proteica
Estrutura Secundária de Proteína
Estrutura Terciária de Proteína
Sódio/química
Proteínas de Transporte de Sódio-Glucose/química
Proteínas de Transporte de Sódio-Glucose/metabolismo
Transportador 2 de Glucose-Sódio/metabolismo
Termodinâmica
Tioaçúcares/metabolismo
Vibrio parahaemolyticus/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Bacterial Proteins); 0 (SLC5A2 protein, human); 0 (Sodium-Glucose Transport Proteins); 0 (Sodium-Glucose Transporter 2); 0 (Thiosugars); 9NEZ333N27 (Sodium); IY9XDZ35W2 (Glucose); X2RN3Q8DNE (Galactose)
[Em] Mês de entrada:1605
[Cu] Atualização por classe:161126
[Lr] Data última revisão:
161126
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150812
[St] Status:MEDLINE


  3 / 22 MEDLINE  
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[PMID]:26098592
[Au] Autor:Chittela S; Reddy TR; Radha Krishna P; Kashyap S
[Ad] Endereço:D-207, Discovery Laboratory, Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India.
[Ti] Título:Ruthenium Catalyzed Stereo/Chemo/Regioselective One-Pot Synthesis of C(2)-C(3) Unsaturated and α-D-Mannopyranosyl Sulfones.
[So] Source:J Org Chem;80(14):7108-16, 2015 Jul 17.
[Is] ISSN:1520-6904
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:An efficient and divergent approach to C(2)-C(3) unsaturated glycosyl and α-D-mannopyranosyl sulfones has been developed via ruthenium-promoted direct glycosylation, oxidation, and dihydroxylation from glycal in one-pot. The presence of stoichiometric amounts of NaIO4 and in situ generation of RuO4 from a RuCl3-NaIO4 reagent system were crucial for chemoselective oxidation of sulfide in the presence of an olefin moiety. The dual-role of ruthenium in sequential glycosylation-oxidation-dihydroxylation is amenable to a wide range of thio acceptors to access α-D-mannopyranosyl sulfones in good yields with high regioselectivity.
[Mh] Termos MeSH primário: Manose/síntese química
Tioaçúcares/síntese química
[Mh] Termos MeSH secundário: Catálise
Glicosilação
Manose/análogos & derivados
Manose/química
Estrutura Molecular
Rutênio/química
Estereoisomerismo
Tioaçúcares/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Thiosugars); 7UI0TKC3U5 (Ruthenium); PHA4727WTP (Mannose)
[Em] Mês de entrada:1602
[Cu] Atualização por classe:150718
[Lr] Data última revisão:
150718
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150623
[St] Status:MEDLINE
[do] DOI:10.1021/acs.joc.5b00975


  4 / 22 MEDLINE  
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[PMID]:25780955
[Au] Autor:Hale KJ; Hough L; Manaviazar S; Calabrese A
[Ti] Título:Rules and stereoelectronic guidelines for the anionic nucleophilic displacement of furanoside and furanose O-sulfonates.
[So] Source:Org Lett;17(7):1738-41, 2015 Apr 03.
[Is] ISSN:1523-7052
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Rules for predicting anionic SN2 displacement viability in furanose and furanoside sulfonates are presented.
[Mh] Termos MeSH primário: Ânions/química
Furanos/química
Tioaçúcares/química
[Mh] Termos MeSH secundário: Estrutura Molecular
Estereoisomerismo
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Anions); 0 (Furans); 0 (Thiosugars)
[Em] Mês de entrada:1510
[Cu] Atualização por classe:150403
[Lr] Data última revisão:
150403
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150318
[St] Status:MEDLINE
[do] DOI:10.1021/acs.orglett.5b00511


  5 / 22 MEDLINE  
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[PMID]:25466184
[Au] Autor:Witczak ZJ; Sarnik J; Czubatka A; Forma E; Poplawski T
[Ad] Endereço:Department of Pharmaceutical Sciences, Nesbitt School of Pharmacy, Wilkes University, 84.W. South Street, Wilkes-Barre, PA 18766, USA. Electronic address: zbigniew.witczak@wilkes.edu.
[Ti] Título:Thio-sugar motif of functional CARB-pharmacophore for antineoplastic activity. Part 2.
[So] Source:Bioorg Med Chem Lett;24(24):5606-5611, 2014 Dec 15.
[Is] ISSN:1464-3405
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Diverse functionalized representatives of (1-4)-S-thiodisaccharides, 6-9 were synthesized and assessed for cytotoxicity and apoptosis against human cancer cell lines (A549, LoVo, MCF-7 and HeLa). The FCP 6 was more active against MCF-7 cells (i.e., an estrogen-dependent breast cancer line), whereas other (1-4)-S-thiodisaccharides showed strongest activity against A549 cells (i.e., a lung adenocarcinoma line). We propose to use a concept of functional 'CARB-pharmacophores' when evaluating a potential for the compounds' general antineoplastic activity. Future studies will determine the reasons for cell-type specificity of these compounds. The thio-sugar motif appears to be a promising lead for future developments.
[Mh] Termos MeSH primário: Antineoplásicos/química
Antineoplásicos/farmacologia
Apoptose/efeitos dos fármacos
Tioaçúcares/química
Tioaçúcares/farmacologia
[Mh] Termos MeSH secundário: Linhagem Celular Tumoral
Sobrevivência Celular/efeitos dos fármacos
Cristalografia por Raios X
Dissacarídeos/química
Células HeLa
Seres Humanos
Concentração Inibidora 50
Células MCF-7
Conformação Molecular
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Antineoplastic Agents); 0 (Disaccharides); 0 (Thiosugars)
[Em] Mês de entrada:1507
[Cu] Atualização por classe:170919
[Lr] Data última revisão:
170919
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:141204
[St] Status:MEDLINE


  6 / 22 MEDLINE  
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[PMID]:25415476
[Au] Autor:Scanlan EM; Corcé V; Malone A
[Ad] Endereço:Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse Street, Dublin 2, Ireland. eoin.scanlan@tcd.ie.
[Ti] Título:Synthetic applications of intramolecular thiol-ene "click" reactions.
[So] Source:Molecules;19(11):19137-51, 2014 Nov 19.
[Is] ISSN:1420-3049
[Cp] País de publicação:Switzerland
[La] Idioma:eng
[Ab] Resumo:The intermolecular thiol-ene reaction is emerging as a highly efficient; free-radical mediated "click" process with diverse applications in biofunctionalisation and materials science. The related intramolecular thiol-ene reactions offer significant potential for the preparation of a wide range of sulphur containing heterocycles including synthetic therapeutics such as cyclic peptides and thiosugars. Herein, we review recent advances in intramolecular thiyl-radical mediated reactions and their applications for synthetic and medicinal chemistry.
[Mh] Termos MeSH primário: Compostos de Sulfidrila/química
[Mh] Termos MeSH secundário: Química Click/métodos
Radicais Livres/química
Peptídeos Cíclicos/química
Tioaçúcares/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T; REVIEW
[Nm] Nome de substância:
0 (Free Radicals); 0 (Peptides, Cyclic); 0 (Sulfhydryl Compounds); 0 (Thiosugars)
[Em] Mês de entrada:1507
[Cu] Atualização por classe:141122
[Lr] Data última revisão:
141122
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:141122
[St] Status:MEDLINE
[do] DOI:10.3390/molecules191119137


  7 / 22 MEDLINE  
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[PMID]:24814342
[Au] Autor:Sasaki E; Zhang X; Sun HG; Lu MY; Liu TL; Ou A; Li JY; Chen YH; Ealick SE; Liu HW
[Ad] Endereço:Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, USA.
[Ti] Título:Co-opting sulphur-carrier proteins from primary metabolic pathways for 2-thiosugar biosynthesis.
[So] Source:Nature;510(7505):427-31, 2014 Jun 19.
[Is] ISSN:1476-4687
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Sulphur is an essential element for life and is ubiquitous in living systems. Yet how the sulphur atom is incorporated into many sulphur-containing secondary metabolites is poorly understood. For bond formation between carbon and sulphur in primary metabolites, the major ionic sulphur sources are the persulphide and thiocarboxylate groups on sulphur-carrier (donor) proteins. Each group is post-translationally generated through the action of a specific activating enzyme. In all reported bacterial cases, the gene encoding the enzyme that catalyses the carbon-sulphur bond formation reaction and that encoding the cognate sulphur-carrier protein exist in the same gene cluster. To study the production of the 2-thiosugar moiety in BE-7585A, an antibiotic from Amycolatopsis orientalis, we identified a putative 2-thioglucose synthase, BexX, whose protein sequence and mode of action seem similar to those of ThiG, the enzyme that catalyses thiazole formation in thiamine biosynthesis. However, no gene encoding a sulphur-carrier protein could be located in the BE-7585A cluster. Subsequent genome sequencing uncovered a few genes encoding sulphur-carrier proteins that are probably involved in the biosynthesis of primary metabolites but only one activating enzyme gene in the A. orientalis genome. Further experiments showed that this activating enzyme can adenylate each of these sulphur-carrier proteins and probably also catalyses the subsequent thiolation, through its rhodanese domain. A proper combination of these sulphur-delivery systems is effective for BexX-catalysed 2-thioglucose production. The ability of BexX to selectively distinguish sulphur-carrier proteins is given a structural basis using X-ray crystallography. This study is, to our knowledge, the first complete characterization of thiosugar formation in nature and also demonstrates the receptor promiscuity of the A. orientalis sulphur-delivery system. Our results also show that co-opting the sulphur-delivery machinery of primary metabolism for the biosynthesis of sulphur-containing natural products is probably a general strategy found in nature.
[Mh] Termos MeSH primário: Actinomycetales/enzimologia
Actinomycetales/genética
Proteínas de Transporte/metabolismo
Ligases/química
Enxofre/metabolismo
Tioaçúcares/metabolismo
[Mh] Termos MeSH secundário: Actinomycetales/metabolismo
Proteínas de Transporte/química
Domínio Catalítico
Genoma Bacteriano/genética
Ligases/genética
Ligases/metabolismo
Modelos Moleculares
Dados de Sequência Molecular
Estrutura Terciária de Proteína
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, N.I.H., EXTRAMURAL; RESEARCH SUPPORT, NON-U.S. GOV'T; RESEARCH SUPPORT, U.S. GOV'T, NON-P.H.S.
[Nm] Nome de substância:
0 (Carrier Proteins); 0 (Thiosugars); 70FD1KFU70 (Sulfur); EC 6.- (Ligases)
[Em] Mês de entrada:1407
[Cu] Atualização por classe:170220
[Lr] Data última revisão:
170220
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:140513
[St] Status:MEDLINE
[do] DOI:10.1038/nature13256


  8 / 22 MEDLINE  
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[PMID]:24079721
[Au] Autor:Malone A; Scanlan EM
[Ad] Endereço:Trinity Biomedical Sciences Institute, Trinity College , 152-160 Pearse Street, Dublin 2, Ireland.
[Ti] Título:Applications of 5-exo-trig thiyl radical cyclizations for the synthesis of thiosugars.
[So] Source:J Org Chem;78(21):10917-30, 2013 Nov 01.
[Is] ISSN:1520-6904
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:The application of thiyl-radical-mediated 5-exo-trig cyclization reactions for the preparation of a series of C-linked 4-thiofuranoside sugars has been investigated. The cyclization reactions were found to proceed in high yield with complete regioselectivity and moderate to excellent diastereoselectivity for a number of benzyl-protected precursors. The diastereoselectivity of the radical cyclization was determined by a number of factors, primarily the stereochemistry at the C-2 position and the nature of the substituents attached to the olefin. The cyclization reactions proceed via transition-state intermediates that favor formation of the 1,2-trans products. For D-sugars, a chairlike transition state is proposed. For L-sugars, both chair- and boatlike transition states could be considered. Inversion of the stereochemistry at C-4 also induced a significant effect on the diastereoselectivity of the radical process. The synthetic route is general for both D- and L-sugars and offers a highly novel and efficient strategy for accessing C-linked 4-thiofuranosides. A fluorescently labeled thiosugar was prepared as a putative glycosidase inhibitor.
[Mh] Termos MeSH primário: Inibidores Enzimáticos/química
Glicosídeo Hidrolases/antagonistas & inibidores
Tioaçúcares/síntese química
[Mh] Termos MeSH secundário: Ciclização
Inibidores Enzimáticos/metabolismo
Estrutura Molecular
Estereoisomerismo
Tioaçúcares/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Enzyme Inhibitors); 0 (Thiosugars); EC 3.2.1.- (Glycoside Hydrolases)
[Em] Mês de entrada:1406
[Cu] Atualização por classe:131101
[Lr] Data última revisão:
131101
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:131002
[St] Status:MEDLINE
[do] DOI:10.1021/jo401900e


  9 / 22 MEDLINE  
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[PMID]:23330717
[Au] Autor:Malone A; Scanlan EM
[Ad] Endereço:School of Chemistry, Trinity College Dublin, Trinity Biomedical Sciences Insitute, 152-160 Pearse Street, Dublin 2, Ireland.
[Ti] Título:Applications of thiyl radical cyclizations for the synthesis of thiosugars.
[So] Source:Org Lett;15(3):504-7, 2013 Feb 01.
[Is] ISSN:1523-7052
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:The use of intramolecular thiyl radical cyclizations for the synthesis of thiosugars has been investigated, and a new free-radical-based methodology for the synthesis of biologically important thiosugars has been developed. The methodology is mild and proceeds via either 6-endo or 5-exo cyclization to furnish the thiosugar ring. This represents the first examples of thiyl radical cyclization being applied to the synthesis of thiosugars.
[Mh] Termos MeSH primário: Compostos de Enxofre/química
Tioaçúcares/síntese química
[Mh] Termos MeSH secundário: Ciclização
Estrutura Molecular
Estereoisomerismo
Tioaçúcares/química
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Sulfur Compounds); 0 (Thiosugars)
[Em] Mês de entrada:1306
[Cu] Atualização por classe:130201
[Lr] Data última revisão:
130201
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:130122
[St] Status:MEDLINE
[do] DOI:10.1021/ol303310u


  10 / 22 MEDLINE  
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[PMID]:23221249
[Au] Autor:Yoshinari N; Kitani N; Konno T
[Ad] Endereço:Osaka University, Toyonaka, Japan. nobuto@chem.sci.osaka-u.ac.jp
[Ti] Título:The first crystal structure of an alkaline metal salt of thioglucose: potassium 1-thio-ß-D-glucoside monohydrate.
[So] Source:Acta Crystallogr C;68(Pt 12):m363-6, 2012 Dec.
[Is] ISSN:1600-5759
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:In the crystal structure of the title hydrated salt, poly[(µ(2)-aqua)(µ(4)-1-sulfido-ß-D-glucoside)potassium], [K(C(6)H(11)O(5)S)(H(2)O)](n) or K(+)·C(6)H(11)O(5)S(-)·H(2)O, each thioglucoside anion coordinates to four K(+) cations through three of its four hydroxy groups, forming a three-dimensional polymeric structure. The negatively charged thiolate group in each anion does not form an efficient coordination bond with a K(+) cation, but forms intermolecular hydrogen bonds with four hydroxy groups, which appears to sustain the polymeric structure. The Cremer-Pople parameters for the thioglucoside ligand (Q = 0.575, θ = 8.233° and Ï• = 353.773°) indicate a slight distortion of the pyranose ring.
[Mh] Termos MeSH primário: Glucosídeos/química
Metais/química
Potássio/química
Sais/química
Tioaçúcares/química
[Mh] Termos MeSH secundário: Cristalografia por Raios X
Ligações de Hidrogênio
Estrutura Molecular
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Glucosides); 0 (Metals); 0 (Salts); 0 (Thiosugars); RWP5GA015D (Potassium)
[Em] Mês de entrada:1303
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:121211
[St] Status:MEDLINE
[do] DOI:10.1107/S0108270112047014



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