thioglucosides

Summary

Top Publications

  1. ncbi Synthetic studies on oligosaccharides composed of 5-thioglucopyranose units
    Yasuharu Morii
    Faculty of Agriculture and Life Science, Hirosaki University, 3 Bunkyo cho, Hirosaki, Aomori 036 8561, Japan
    Bioorg Med Chem 13:5113-44. 2005
  2. ncbi Mycobacterium tuberculosis antigen 85A and 85C structures confirm binding orientation and conserved substrate specificity
    Donald R Ronning
    Department of Biochemistry and Biophysics, Texas A and M University, College Station, TX 77843 2128, USA
    J Biol Chem 279:36771-7. 2004
  3. ncbi Towards engineering glucosinolates into non-cruciferous plants
    Fernando Geu-Flores
    Plant Biochemistry Laboratory, VKR Research Centre Pro Active Plants, Department of Plant Biology and Biotechnology, Faculty of Life Sciences, University of Copenhagen, 40 Thorvaldsensvej, 1871, Frederiksberg C, Denmark
    Planta 229:261-70. 2009
  4. ncbi Glucosinolate engineering identifies a gamma-glutamyl peptidase
    Fernando Geu-Flores
    Plant Biochemistry Laboratory, Department of Plant Biology, Faculty of Life Sciences, University of Copenhagen, Frederiksberg, Denmark
    Nat Chem Biol 5:575-7. 2009
  5. ncbi Glycine conjugates in a lepidopteran insect herbivore--the metabolism of benzylglucosinolate in the cabbage white butterfly, Pieris rapae
    Fredd Vergara
    Max Planck Institute for Chemical Ecology, Beutenberg Campus, Hans Knoll Strasse 8, 07745 Jena, Germany
    Chembiochem 7:1982-9. 2006
  6. ncbi Cytochrome P450 CYP79A2 from Arabidopsis thaliana L. Catalyzes the conversion of L-phenylalanine to phenylacetaldoxime in the biosynthesis of benzylglucosinolate
    U Wittstock
    Plant Biochemistry Laboratory, Department of Plant Biology, and Center for Molecular Plant Physiology PlaCe, The Royal Veterinary and Agricultural University, Thorvaldsensvej 40, DK 1871 Frederiksberg C, Copenhagen, Denmark
    J Biol Chem 275:14659-66. 2000
  7. ncbi Mixtures of n-octyl-beta-D-glucoside and triethylene glycol mono-n-octyl ether: phase behavior and micellar structure near the liquid-liquid phase boundary
    Gabriella M Santonicola
    Center for Molecular and Engineering Thermodynamics, Department of Chemical Engineering, University of Delaware, Newark, Delaware 19716, USA
    Langmuir 21:9955-63. 2005
  8. ncbi Synthesis of novel 2-phenylsulfonylhydrazono-3-(2',3',4',6'-tetra-O-acetyl-beta-d-glucopyranosyl)thiazolidine-4-ones from thiosemicarbazide precursors
    Yu Xin Li
    State Key Laboratory of Elemento organic Chemistry, Nankai University, Tianjin 300071, China
    Carbohydr Res 341:2867-70. 2006
  9. ncbi Bromonium ion-promoted glycosidic bond formation and simultaneous bromination of an activated aryl aglycon
    Zhi Hui Qin
    Department of Bioorganic Chemistry, School of Pharmaceutical Sciences, Beijing Medical University, Beijing 100083, PR China
    Carbohydr Res 337:31-6. 2002
  10. ncbi Synthesis of 4-cyanophenyl 1,5-dithio-beta-D-glucopyranoside and its 6-deoxy, as well as 6-deoxy-5-ene derivatives as oral antithrombotic agents
    E Bozó
    Institute for Drug Research, Budapest, Hungary
    Carbohydr Res 304:271-80. 1997

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Scientific Experts

Detail Information

Publications116 found, 100 shown here

  1. ncbi Synthetic studies on oligosaccharides composed of 5-thioglucopyranose units
    Yasuharu Morii
    Faculty of Agriculture and Life Science, Hirosaki University, 3 Bunkyo cho, Hirosaki, Aomori 036 8561, Japan
    Bioorg Med Chem 13:5113-44. 2005
    ..This was applied for preparation of sulfur-substituted gentiobiosides 1 and 46...
  2. ncbi Mycobacterium tuberculosis antigen 85A and 85C structures confirm binding orientation and conserved substrate specificity
    Donald R Ronning
    Department of Biochemistry and Biophysics, Texas A and M University, College Station, TX 77843 2128, USA
    J Biol Chem 279:36771-7. 2004
    ....
  3. ncbi Towards engineering glucosinolates into non-cruciferous plants
    Fernando Geu-Flores
    Plant Biochemistry Laboratory, VKR Research Centre Pro Active Plants, Department of Plant Biology and Biotechnology, Faculty of Life Sciences, University of Copenhagen, 40 Thorvaldsensvej, 1871, Frederiksberg C, Denmark
    Planta 229:261-70. 2009
    ..In summary, we transferred the last three steps of the benzylglucosinolate pathway to tobacco as a first step towards engineering glucosinolates into non-cruciferous plants...
  4. ncbi Glucosinolate engineering identifies a gamma-glutamyl peptidase
    Fernando Geu-Flores
    Plant Biochemistry Laboratory, Department of Plant Biology, Faculty of Life Sciences, University of Copenhagen, Frederiksberg, Denmark
    Nat Chem Biol 5:575-7. 2009
    ....
  5. ncbi Glycine conjugates in a lepidopteran insect herbivore--the metabolism of benzylglucosinolate in the cabbage white butterfly, Pieris rapae
    Fredd Vergara
    Max Planck Institute for Chemical Ecology, Beutenberg Campus, Hans Knoll Strasse 8, 07745 Jena, Germany
    Chembiochem 7:1982-9. 2006
    ..rapae faeces extracts. This is the first description of such conjugates from lepidopteran insects...
  6. ncbi Cytochrome P450 CYP79A2 from Arabidopsis thaliana L. Catalyzes the conversion of L-phenylalanine to phenylacetaldoxime in the biosynthesis of benzylglucosinolate
    U Wittstock
    Plant Biochemistry Laboratory, Department of Plant Biology, and Center for Molecular Plant Physiology PlaCe, The Royal Veterinary and Agricultural University, Thorvaldsensvej 40, DK 1871 Frederiksberg C, Copenhagen, Denmark
    J Biol Chem 275:14659-66. 2000
    ..This strongly indicates that the biosynthesis of glucosinolates has evolved based on a cyanogenic predisposition...
  7. ncbi Mixtures of n-octyl-beta-D-glucoside and triethylene glycol mono-n-octyl ether: phase behavior and micellar structure near the liquid-liquid phase boundary
    Gabriella M Santonicola
    Center for Molecular and Engineering Thermodynamics, Department of Chemical Engineering, University of Delaware, Newark, Delaware 19716, USA
    Langmuir 21:9955-63. 2005
    ..Colloidal silica particles were then added to these surfactant mixtures and were found to aggregate at conditions near the cloud point. This finding is relevant to current strategies for protein crystallization...
  8. ncbi Synthesis of novel 2-phenylsulfonylhydrazono-3-(2',3',4',6'-tetra-O-acetyl-beta-d-glucopyranosyl)thiazolidine-4-ones from thiosemicarbazide precursors
    Yu Xin Li
    State Key Laboratory of Elemento organic Chemistry, Nankai University, Tianjin 300071, China
    Carbohydr Res 341:2867-70. 2006
    ..Furthermore, the effect of various solvents at reflux temperature on the reactions of ethyl bromoacetate with the related thiosemicarbazides was investigated...
  9. ncbi Bromonium ion-promoted glycosidic bond formation and simultaneous bromination of an activated aryl aglycon
    Zhi Hui Qin
    Department of Bioorganic Chemistry, School of Pharmaceutical Sciences, Beijing Medical University, Beijing 100083, PR China
    Carbohydr Res 337:31-6. 2002
    ..Concurrently with formation of the glycosidic bond, bromination took place on the activated aromatic ring of a 4-methoxyphenyl aglycon...
  10. ncbi Synthesis of 4-cyanophenyl 1,5-dithio-beta-D-glucopyranoside and its 6-deoxy, as well as 6-deoxy-5-ene derivatives as oral antithrombotic agents
    E Bozó
    Institute for Drug Research, Budapest, Hungary
    Carbohydr Res 304:271-80. 1997
    ..The compounds obtained on deacetylation of 6, 9, 14, 30 and 35 showed a stronger oral antithrombotic effect in rats as compared to beciparcil, used as reference...
  11. ncbi Induction of myrosinase gene expression and myrosinase activity in radish hypocotyls by phototropic stimulation
    Kosumi Yamada
    Institute of Applied Biochemistry, University of Tsukuba, Tsukuba, Ibaraki 305 8572, Japan
    J Plant Physiol 160:255-9. 2003
    ....
  12. ncbi A novel three-dimensional crystal of bacteriorhodopsin obtained by successive fusion of the vesicular assemblies
    K Takeda
    Graduate School of Science, Nagoya University, Nagoya, 464 8602, Japan
    J Mol Biol 283:463-74. 1998
    ..The present result offers a unique crystallization method that may be applicable to such membrane proteins that are liable to denature in the presence of an excess amount of detergent...
  13. ncbi Electrospray mass spectra of three proprietary detergents
    E Yang-Boja
    National Heart, Lung and Blood Institute, National Institutes of Health, Bethesda, Maryland 20892, USA
    Anal Biochem 285:205-10. 2000
    ....
  14. ncbi Sustained release of nucleic acids from polymeric nanoparticles using microemulsion precipitation in supercritical carbon dioxide
    Jun Ge
    Department of Chemistry, Stanford University, 333 Campus Drive, Stanford, CA 94305 5080, USA
    Chem Commun (Camb) 46:9034-6. 2010
    ..The microemulsion consists of a transfer RNA aqueous solution (water phase), dichloromethane containing poly(l-lactic acid)-poly(ethylene glycol) (oil phase), the surfactant n-octyl β-D-glucopyranoside, and the cosurfactant n-butanol...
  15. ncbi Ultrasonication-assisted spray ionization mass spectrometry for on-line monitoring of organic reactions
    Tsung Yi Chen
    Department of Applied Chemistry, National Chiao Tung University, Hsinchu 300, Taiwan
    Chem Commun (Camb) 46:8347-9. 2010
    ..A straightforward on-line monitoring of organic reactions by ultrasonication-assisted spray ionization mass spectrometry (UASI MS) is demonstrated in this work...
  16. pmc Herbicidal activity of glucosinolate degradation products in fermented meadowfoam ( Limnanthes alba ) seed meal
    Jan F Stevens
    Departments of Pharmaceutical Sciences and Statistics and the Columbia Basin Agricultural Research Center, Oregon State University, Corvallis, Oregon 97331, USA
    J Agric Food Chem 57:1821-6. 2009
    ..96). The results of this study open new possibilities for the refinement of glucosinolate-containing seed meals for use as bioherbicides...
  17. ncbi Sequestration of plant-derived phenolglucosides by larvae of the leaf beetle Chrysomela lapponica: thioglucosides as mechanistic probes
    Jürgen Kuhn
    Max Planck Institute for Chemical Ecology, Hans Knöll Str 8, D 07745, Jena, Germany
    J Chem Ecol 33:5-24. 2007
    ..By using systematically modified and hydrolysis-resistant thioglucosides as structural mimics of the plant-derived glucosides, e.g...
  18. ncbi Synthesis of ethyl 2-acetamido-6-S-(5-amino-5-deoxy-beta-D- arabinopyranosyl)-2-deoxy-1,6-dithio-beta-D-glucopyranoside: a sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide
    K Suzuki
    Department of Life Science, Faculty of Bioscience and Biotechnology, Tokyo Institute of Technology, Yokohama, Japan
    Carbohydr Res 323:14-27. 2000
    ..The sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide was shown to be formed from 5-amino-5-deoxy-D-arabinose and ethyl 2-acetamido-2-deoxy-1,6-dithio-beta-D-glucopyranoside in an acidic buffer solution...
  19. ncbi N-octyl-beta-thioglucoside enhances the transdermal permeation of ketotifen
    S Narasimha Murthy
    Pharmaceutical and Biomedical Sciences, Raabe College of Pharmacy, Ohio Northern University, Ada, Ohio 45810, USA
    Pharmazie 61:75-6. 2006
  20. ncbi Stereocontrolled synthesis of sulfur-linked analogues of the branched tetrasaccharide repeating-unit of the immunostimulant polysaccharide schizophyllan and of its beta-(1-->3)-branched, beta-(1-->6)-linked isomer
    M O Contour-Galcera
    Département de Recherche Fondamentale sur la Matière Condensée SESAM, CEntre d Etudes de Grenoble, France
    Carbohydr Res 281:119-28. 1996
    ....
  21. pmc Spatial organization of the glucosinolate-myrosinase system in brassica specialist aphids is similar to that of the host plant
    Matthew Bridges
    Department of Agricultural Sciences, Imperial College at Wye, University of London, Wye, Kent TN25 5AH, UK
    Proc Biol Sci 269:187-91. 2002
    ..Brevicoryne brassicae (cabbage aphid) and Lipaphis erysimi (turnip aphid) can sequester glucosinolates (thioglucosides) from their host plants, yet avoid the generation of toxic degradation products by compartmentalizing ..
  22. ncbi Molecular models and mutational analyses of plant specifier proteins suggest active site residues and reaction mechanism
    Wolfgang Brandt
    Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120, Halle Saale, Germany
    Plant Mol Biol 84:173-88. 2014
    ..Glucosinolates are thioglucosides that are stored separately from their hydrolytic enzymes, myrosinases, in plant tissue...
  23. ncbi Light-induced O-glycosylation of unprotected deoxythioglycosyl donors
    Mayuka Nakanishi
    Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3 14 1 Hiyoshi, Yokohama 223 8522, Japan
    Org Biomol Chem 11:5079-82. 2013
    ..In some cases, the use of p-methoxyboronic acid was very effective in temporary protection of the 1,3-diol (C4 and C6 positions) of the unprotected glycosyl donors to increase the yields of the obtained O-glycosides. ..
  24. ncbi Escherichia coli β-galactosidase inhibitors through modifications at the aglyconic moiety: experimental evidence of conformational distortion in the molecular recognition process
    Luis Calle
    Chemical and Physical Biology, Centro de Investigationes Biològicas, CSIC, Ramiro de Maetzu 9, 28040 Madrid, Spain
    Chemistry 19:4262-70. 2013
    ..The bound conformations of the ligand are adapted in the enzymatic pocket with a variety of hydrogen-bond, van der Waals, and stacking interactions...
  25. ncbi New classes of carborane-appended 5-thio-D-glucopyranose derivatives
    Rashmirekha Satapathy
    Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115 2862, USA
    Dalton Trans 41:8982-8. 2012
    ..The accumulation of both 18 and 19 was found to occur in a temperature dependent manner. The higher accumulation of 18 suggested excellent promise for it to be a candidate for further evaluation as a future BNCT agent...
  26. ncbi Distinctive inhibition of O-GlcNAcase isoforms by an alpha-GlcNAc thiolsulfonate
    Eun J Kim
    Laboratory of Cell Biochemistry and Biology, NIDDK, National Institute of Health, Bethesda, Maryland 20892, USA
    J Am Chem Soc 129:14854-5. 2007
    ..Covalent attachment of GlcNAc to the HAT domain of long OGA dramatically changes its properties with respect to enzymatic activity and caspase-3 cleavage...
  27. ncbi Characterization of mixed non-ionic surfactants n-octyl-β-D-thioglucoside and octaethylene-glycol monododecyl ether: micellization and microstructure
    C Carnero Ruiz
    Departamento de Fisica Aplicada II, Escuela Politecnica Superior, Universidad de Malaga, Malaga, Spain
    J Colloid Interface Sci 361:178-85. 2011
    ..All these observations were attributed to the different structure of the head groups of both surfactants and, as a consequence, to their different hydration...
  28. ncbi Synthesis of sulfur-linked analogues of nigerose, laminarabiose, laminaratriose, gentiobiose, gentiotriose, and laminaran trisaccharide Y
    M O Contour-Galcera
    Département de Recherche Fondamentale sur la Matière Condensée SESAM, CEntre d Etudes de Grenoble, France
    Carbohydr Res 281:99-118. 1996
    ..The preparation of thiotrisaccharides 16, 29, and 37 involved a mixed approach...
  29. ncbi Regioselective one-pot protection, protection-glycosylation and protection-glycosylation-glycosylation of carbohydrates: a case study with D-glucose
    Teng Yi Huang
    Genomics Research Center, Academia Sinica, No 128, Section 2, Academia Road, Taipei 115, Taiwan
    Org Biomol Chem 12:376-82. 2014
    ..starting material, we herein show the one-pot preparations of diols, triols and fully protected derivatives of thioglucosides, and, more importantly, we generated building blocks in situ that effectively acted as glycosyl donors and ..
  30. ncbi "Super armed" glycosyl donors: conformational arming of thioglycosides by silylation
    Christian Marcus Pedersen
    Department of Chemistry, University of Aarhus, Langelandsgade 140, DK 8000 Aarhus C, Denmark
    J Am Chem Soc 129:9222-35. 2007
    ..TBS), on the 2-, 3-, and 4-OH groups were found to have superior reactivity compared with benzylated thioglucosides. The enhanced reactivity is explained by the stereoelectronic effects associated with the conformational ..
  31. ncbi Simultaneous regioselective protection of phenyl 1-thioglucosides at the C-3 and C-6 or at the C-2 and C-6 hydroxy groups
    Yasunori Ikeda
    School of Science and Technology, Kwansei Gakuin University, 2 1 Gakuen, Sanda 669 1337, Japan
    Carbohydr Res 337:1499-501. 2002
    ..The C-2 and C-6 hydroxy groups of the alpha-thioglucoside were selectively protected with tert-butyldiphenylsilyl trifluoromethanesulfonate...
  32. ncbi Contrasting reactivity of thioglucoside and selenoglucoside donors towards promoters: implications for glycosylation stereocontrol
    Renate M van Well
    Centre for Carbohydrate Chemistry, School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich NR4 7TJ, UK
    Carbohydr Res 341:1391-7. 2006
    ....
  33. ncbi Benzylglucosinolate, benzylisothiocyanate, and myrosinase activity in papaya fruit during development and ripening
    Maria Rosecler Miranda Rossetto
    Laboratorio de Quimica, Bioquimica e Biologia Molecular de Alimentos, Departamento de Alimentos e Nutricao Experimental, FCF, Universidade de Sao Paulo, Avenida Lineu Prestes 580, Bloco 14, CEP 05508 900, Sao Paulo SP, Brazil
    J Agric Food Chem 56:9592-9. 2008
    ....
  34. ncbi Electrochemical generation of glycosyl triflate pools
    Toshiki Nokami
    Department of Synthetic Chemistry, Kyoto University, Katsura, Kyoto 615 8510, Japan
    J Am Chem Soc 129:10922-8. 2007
    ..were generated and accumulated by the low-temperature electrochemical oxidation of thioglycosides such as thioglucosides, thiogalactosides, and thiomannosides in the presence of tetrabutylammonium triflate (Bu(4)NOTf) as a ..
  35. ncbi Use of octyl beta-thioglucopyranoside in two-dimensional crystallization of membrane proteins
    M Chami
    Section de Recherche, Institut Curie, UMR CNRS 168 et LRC CEA 8, 11 rue Pierre et Marie Curie, 75231 Paris, France
    J Struct Biol 133:64-74. 2001
    ....
  36. ncbi Thioglucosidase activity from Sphingobacterium sp. strain OTG1
    G H Meulenbeld
    Department of Agrotechnology and Food Sciences, Wageningen University, The Netherlands
    Appl Microbiol Biotechnol 56:700-6. 2001
    ..Besides OTG, various other thioglucosides were hydrolysed by the novel thioglucosidase, with almost the same activities regardless of the nature of the ..
  37. ncbi Intestinal microflora plays a crucial role in the genotoxicity of the cooked food mutagen 2-amino-3-methylimidazo [4,5-f]quinoline
    F Kassie
    Institute of Cancer Research, Borschkegasse 8a, A 1090 Vienna, Austria
    Carcinogenesis 22:1721-5. 2001
    ..We conclude that the alkaline SCGE assay with rats harbouring different flora opens new possibilities to investigate the role of intestinal bacteria on health risks caused by dietary carcinogens...
  38. ncbi [Micelle-mediated extraction for concentrating conjugated bilirubin in urine]
    T Matsudo
    Tokyo University of Pharmacy and Life Science, 1432 1 Horinouchi, Hachioji, Tokyo 192 0392, Japan
    Yakugaku Zasshi 121:191-2. 2001
    ..Conjugated bilirubin was successfully determined in the concentration range from 0.05 microgram/ml to 5 micrograms/ml with a 96-well microplate reader absorption spectrophotometer...
  39. ncbi Purification of the H(+)-ATPase from chloroplasts
    R D Kirch
    Biologisches Institut, Universitat Stuttgart, Germany
    Acta Physiol Scand Suppl 607:9-12. 1992
    ..The results indicate that the enzyme can be purified without Triton X-100 and retain full activity...
  40. ncbi Synthesis of S-linked glycoconjugates and S-disaccharides by thiol-ene coupling reaction of enoses
    László Lázár
    Research Group for Carbohydrates, University of Debrecen, P O Box 94, H 4010 Debrecen, Hungary
    Org Lett 14:4650-3. 2012
    ..Addition of glycosyl thiols to a 2,3-unsaturated glycoside also proceeded with good selectivity and afforded a series of 3-deoxy-S-disaccharides...
  41. pmc Turning the 'mustard oil bomb' into a 'cyanide bomb': aromatic glucosinolate metabolism in a specialist insect herbivore
    Einar J Stauber
    Institute of Pharmaceutical Biology, Technische Universitat Braunschweig, Braunschweig, Germany
    PLoS ONE 7:e35545. 2012
    ....
  42. ncbi Dermacentor andersoni: salivary gland proteins suppressing T-lymphocyte responses to concanavalin A in vitro
    D K Bergman
    Department of Entomology, Oklahoma State University, Stillwater 74078, USA
    Exp Parasitol 81:262-71. 1995
    ..Salivary gland preparative SDS-PAGE fractions containing one or more soluble polypeptides or proteins with molecular weights in the range 36 to 43 kDa significantly suppressed murine splenocyte responses to ConA in vitro...
  43. pmc Antigen 85C inhibition restricts Mycobacterium tuberculosis growth through disruption of cord factor biosynthesis
    Thulasi Warrier
    Department of Immunology, Max Planck Institute for Infection Biology, Berlin, Germany
    Antimicrob Agents Chemother 56:1735-43. 2012
    ..tuberculosis envelope. I3-AG85 inhibited the division of and reduced TDM synthesis in an M. tuberculosis strain deficient in Ag85C. Our results indicate that Ag85 proteins are promising targets for novel antimycobacterial drug design...
  44. ncbi Differentiating the 2,3-diols of glucopyranosides by 4,6-O-benzylidene-protected-1,2-D-glucopyranosylorthoesters strategy
    Guangfa Wang
    College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China
    Carbohydr Res 346:2368-73. 2011
    ..Stable thioglucosides were employed as the starting materials to prepare the corresponding 1,2-orthoesters...
  45. ncbi Acyl and silyl group effects in reactivity-based one-pot glycosylation: synthesis of embryonic stem cell surface carbohydrates Lc4 and IV(2)Fuc-Lc4
    Yun Hsu
    Genomics Research Center, Academia Sinica, 128, Section 2, Academia Road, Taipei 115, Taiwan
    J Am Chem Soc 134:4549-52. 2012
    Relative reactivity evaluations showed the graded arming of toluenyl thioglucosides by variously positioned silyl groups but not by their acyl counterparts...
  46. ncbi Alpha-(1-->2)-, and alpha-(1-->3)-, and alpha-(1-->6)-linked thioglycosidic disaccharides: syntheses and anti-HIV testing of thiokojibiose octaacetate, thionigerose, and thioisomaltose
    R N Comber
    Organic Chemistry Department, Southern Research Institute, Birmingham, Alabama 35255 5305
    Carbohydr Res 262:245-55. 1994
    ..Anti-HIV activity was noted only with thiokojibiose octaacetate and its 1-thio analogue (14), which had IC50 values of 51 and 48 micrograms/mL in CEM cells, respectively...
  47. pmc Interaction of octyl-beta-thioglucopyranoside with lipid membranes
    M R Wenk
    Department of Biophysical Chemistry, Biocenter of the University of Basel, Switzerland
    Biophys J 73:2565-74. 1997
    ..As the partition constant remains unchanged, the increase in enthalpy is compensated for by a corresponding increase in entropy, presumably caused by a restructuring of the membrane hydration layer...
  48. ncbi 5-Nitro-2-pyridyl-1-thioglucosides: application in synthesis of analogues of glycosyltransferases natural substrates
    Gabriela Pastuch
    Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Faculty of Chemistry, Silesian University of Technology, Krzywoustego 4, 44 100 Gliwice, Poland
    Acta Pol Pharm 67:642-51. 2010
    5-Nitro-2-pyridyl-1-thioglucosides were used in synthesis of complex uridine derivatives (13-16) in two different sequences of reactions...
  49. pmc Effects of glucosinolates and flavonoids on colonization of the roots of Brassica napus by Azorhizobium caulinodans ORS571
    K J O'Callaghan
    Plant Science Division, University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom
    Appl Environ Microbiol 66:2185-91. 2000
    ....
  50. ncbi Sulfur-containing amides from Entada phaseoloides
    Hui Xiong
    College of Pharmacy, South Central University for Nationalities, Wuhan 430074, China
    Yao Xue Xue Bao 45:624-6. 2010
    ..Compound 1 is a new compound. Compound 4 is isolated from the genus Entada for the first time...
  51. ncbi Chemical synthesis and microvascular effects of new nitric oxide donors in humans
    Faisel Khan
    Vascular Diseases Research Unit, University Department of Medicine, Ninewells Hospital and Medical School, Dundee DD1 9SY, UK
    Clin Sci (Lond) 105:577-84. 2003
    ..Since such compounds release NO in a non-enzymic manner following topical application, they might produce an attractive therapeutic source of localized NO delivery without inducing systemic side effects...
  52. ncbi Molecular dynamics characterization of n-octyl-beta-D-glucopyranoside micelle structure in aqueous solution
    Praveen Konidala
    Institute of Thermodynamics, Helmut Schmidt University University of the Federal Armed Forces Hamburg, Holstenhofweg 85, D 22043 Hamburg, Germany
    J Mol Graph Model 25:77-86. 2006
    ..This result indicates that these atoms are pointed outwards at the hydrophilic/hydrophobic interface, form hydrogen bonds with the water molecules, and thus hydrate the micelle surface effectively...
  53. ncbi Three 1-thio-beta-D-glucopyranosides from the seeds of Afrostyrax lepidophyllus Mildbr
    Annie Ngono Ngane
    SONAS, UFR des Sciences Pharmaceutiques, 16, Bd Daviers, F 49100 Angers, France
    Carbohydr Res 341:2799-802. 2006
    ..Moreover, Afrostyraxthiosides A, B and C constitute a new subclass of 1-thioglycosides isolated from natural sources...
  54. ncbi Solubilization and structural stability of bacteriorhodopsin with a mild nonionic detergent, n-Octyl-β-thioglucoside
    Azusa Asada
    Department of Chemistry and Chemical Biology, Gunma University, Kiryu, Gunma, Japan
    Biosci Biotechnol Biochem 75:376-8. 2011
    ..In comparison with OG-solubilized bR, the structural stability of OTG-solubilized bR was high in the dark and under light illumination. These results indicate that OTG is a detergent superior to OG for solubilizing bR molecules...
  55. ncbi Effect of two different extracts of red maca in male rats with testosterone-induced prostatic hyperplasia
    Gustavo F Gonzales
    Biological and Physiological Sciences, Cayetano Heredia University, Lima, Peru
    Asian J Androl 9:245-51. 2007
    ..To determine the effect of two different extracts of red maca in male rats...
  56. pmc Bacteriorhodopsin/amphipol complexes: structural and functional properties
    Yann Gohon
    Laboratoire de Physico Chimie Moléculaire des Membranes Biologiques, Centre National de la Recherche Scientifique, and Université Paris 7, Institut de Biologie Physico Chimique, Paris, France
    Biophys J 94:3523-37. 2008
    ..In the absence of free APol, BR/APol particles can autoassociate into small or large ordered fibrils...
  57. ncbi Desulfation followed by sulfation: metabolism of benzylglucosinolate in Athalia rosae (Hymenoptera: Tenthredinidae)
    Sebastian E W Opitz
    Department of Chemical Ecology, Bielefeld University, Bielefeld, Germany
    Chembiochem 12:1252-7. 2011
    ..This is the first report on glucosinolate metabolism of a glucosinolate-sequestering insect species...
  58. ncbi N-phenylglucosylamine hydrolysis: a mechanistic probe of β-glucosidase
    Ying Na
    Department of Chemistry, Tulane University, New Orleans, LA 70118, USA
    Bioorg Chem 39:111-3. 2011
    ..These results are consistent with the generally accepted mechanism involving exocyclic bond cleavage by these enzymes...
  59. ncbi Glycosylation with N-Troc-protected glycosyl donors
    U Ellervik
    Chemical Center, Lund Institute of Technology, University of Lund, Sweden
    Carbohydr Res 280:251-60. 1996
    ..The N-Troc protecting group can be removed by reduction with zinc, which allows selective N-deprotection in oligosaccharides containing both N-Troc and N-Phth groups...
  60. pmc Modulation of sulfur metabolism enables efficient glucosinolate engineering
    Morten E Møldrup
    Department of Plant Biology and Biotechnology, Faculty of Life Sciences, University of Copenhagen, Frederiksberg C, Denmark
    BMC Biotechnol 11:12. 2011
    ..However, the accumulation did not reach the expected levels, leaving room for further optimization...
  61. ncbi Synthesis and evaluation of anti-tubercular activity of new dithiocarbamate sugar derivatives
    Yasuhiro Horita
    Department of Molecular Health Sciences, Graduate School of Pharmaceutical Sciences, Nagoya City University, Nagoya, Japan
    Bioorg Med Chem Lett 21:899-903. 2011
    ..Overall, this study presents OCT313HK as a novel and potent compound against MTB, particularly promising to overcome drug resistance...
  62. ncbi Specificity of β1,4-galactosyltransferase inhibition by 2-naphthyl 2-butanamido-2-deoxy-1-thio-β-D-glucopyranoside
    Yin Gao
    Department of Medicine, Division of Rheumatology, Queen s University, Kingston, ON, K7L 3N6, Canada
    Glycoconj J 27:673-84. 2010
    ..In addition, 612 potently inhibits β4GalT in cell homogenates and thus allows assaying β3GalT activity in the presence of β4GalT...
  63. ncbi Glass transition behavior of octyl β-D-glucoside and octyl β-D-thioglucoside/water binary mixtures
    Shigesaburo Ogawa
    Department of Applied Chemistry, Graduate School of Science and Technology, Keio University, 3 14 1 Hiyoshi, Kohoku Ku, Yokohama 223 8522, Japan
    Carbohydr Res 345:2534-41. 2010
    ..And the highest temperature of phase transition from lamellar to isotropic solution was observed at around 50% molar concentration. It was expected that non-percolated state of water existed in extremely higher concentration ranges...
  64. ncbi Performance of a 99mTc-labelled 1-thio-beta-D-glucose 2,3,4,6-tetra-acetate analogue in the detection of infections and tumours in mice: a comparison with [18F]FDG
    Mick M Welling
    Molecular Imaging Laboratories Leiden, Department of Radiology, Section Nuclear Medicine, Leiden University Medical Center, 2333 ZALeiden, The Netherlands
    Nucl Med Commun 31:239-48. 2010
    ....
  65. ncbi The synthesis of compatible solute analogues-solvent effects on selective glycosylation
    Eva C Lourenço
    Instituto de Tecnologia Quimica e Biologica, Universidade Nova de Lisboa, Apartado 127, 2780 901 Oeiras, Portugal
    Carbohydr Res 346:163-8. 2011
    ..The corresponding thiogalactoside underwent similar glycosylations with the same solvents but with low anomer selectivity. These glycosides are key intermediates for the synthesis of new analogues of compatible solutes...
  66. ncbi Synthesis of raphanuside, an unusual oxathiane-fused thioglucoside isolated from the seeds of Raphanus sativus L
    Fei Yang
    State Key Laboratory of Bio organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
    Carbohydr Res 345:309-14. 2010
    ..Raphanuside (1), an unusual oxathiane-fused thioglycoside isolated from the seeds of Raphanus sativus L., was synthesized via 10 steps and in 11% overall yield...
  67. ncbi A direct synthetic approach to uracil anhydrothionucleoside derivatives
    Nouria A Al-Awadi
    Chemistry Department, Faculty of Science, Kuwait University, PO Box 5969, Safat 13060, Kuwait
    Carbohydr Res 344:2322-8. 2009
    ..Heating at 210-220 degrees C was found to give the best yield of a single isomer. The structures of the new anhydrothionucleosides were confirmed by NMR techniques...
  68. ncbi Tropaeolum tuberosum (Mashua) reduces testicular function: effect of different treatment times
    I Cárdenas-Valencia
    Department of Biological and Physiological Sciences, Faculty of Sciences and Philosophy and Instituto de Investigaciones de la Altura, Universidad Peruana Cayetano Heredia, Lima, Peru
    Andrologia 40:352-7. 2008
    ..Finally, mashua reduces testicular function after one spermatogenic cycle by reducing spermatid and sperm number, DSP and epididymal sperm transit time...
  69. pmc The genetic basis of constitutive and herbivore-induced ESP-independent nitrile formation in Arabidopsis
    Meike Burow
    Institut fur Pharmazeutische Biologie, Technische Universitat Braunschweig, 38106 Braunschweig, Germany
    Plant Physiol 149:561-74. 2009
    Glucosinolates are a group of thioglucosides that are components of an activated chemical defense found in the Brassicales. Plant tissue damage results in hydrolysis of glucosinolates by endogenous thioglucosidases known as myrosinases...
  70. ncbi Synthesis of antimitotic thioglycosides: in vitro and in vivo evaluation of their anticancer activity
    Isabel García-Álvarez
    Hospital Nacional de Paraplejicos, SESCAM, Finca La Peraleda s n, 45071 Toledo, Spain
    J Med Chem 54:6949-55. 2011
    ..In vivo experiments in nude mice bearing an implanted C6 glioma showed that the α-thioglycoside 3 reduced tumor volume, while the O-glycosyl derivative was inactive, highlighting the importance of using enzyme resistant glycosides...
  71. ncbi Detergents affect insulin binding, tyrosine kinase activity and oligomeric structure of partially purified insulin receptors
    V Leray
    INSERM U 338, Centre de Neurochimie, Strasbourg, France
    Arch Biochem Biophys 294:22-9. 1992
    ..These alterations in the oligomerization status of the insulin receptor may explain the deleterious effects observed with both Chaps and octylglucoside at higher concentrations...
  72. ncbi Mechanism-based inhibition and stereochemistry of glucosinolate hydrolysis by myrosinase
    S Cottaz
    Centre de Recherches sur les Macromolecules Vegetales, Centre National de la Recherche Scientifique, Grenoble, France
    Biochemistry 35:15256-9. 1996
    ..This enzyme, which is the only glycosidase able to hydrolyze these naturally occurring thioglucosides, has been found previously to display strong sequence similarities with family 1 O-glycosidases...
  73. pmc Electron cryomicroscopy of bacteriorhodopsin vesicles: mechanism of vesicle formation
    N D Denkov
    Protein Array Project, ERATO, JRDC, Tsukuba Research Consortium, Japan
    Biophys J 74:1409-20. 1998
    ..The conditions for vesicle formation and the mechanical properties of the vesicles could also be of interest with respect to the potential technological application of the bR vesicles as light energy converters...
  74. ncbi Highly selective separation of rhodopsin from bovine rod outer segment membranes using combination of divalent cation and alkyl(thio)glucoside
    T Okada
    Department of Physics, Nagoya University, Japan
    Photochem Photobiol 67:495-9. 1998
    ..The present result represents a unique example of selective solubilization of a specific membrane protein from highly aggregated membranes...
  75. ncbi Reactions of a glucosinolate breakdown product (benzyl isothiocyanate) with myoglobin
    H Rawel
    Institute of Nutritional Science, University of Potsdam, Germany
    Phytochemistry 48:1305-11. 1998
    ..In addition, the Mr distribution of the reaction products was determined by MALDI-TOF-mass spectrometry and the overall degree of derivatization calculated from the spectra...
  76. ncbi The family 1 beta-glucosidases from Pyrococcus furiosus and Agrobacterium faecalis share a common catalytic mechanism
    M W Bauer
    Department of Chemical Engineering, North Carolina State University, Raleigh 27695, USA
    Biochemistry 37:17170-8. 1998
    ....
  77. ncbi Renal drug targeting using a vector "alkylglycoside"
    K Suzuki
    Drug Delivery System Institute, Ltd, Noda shi, Chiba, Japan
    J Pharmacol Exp Ther 288:57-64. 1999
    ..In addition, these renally targeted derivatives inhibited the binding of [3H]Glc-S-C7-Me to the kidney membrane fraction. Our findings allow us to conclude that the alkylglycoside is a suitable candidate vector for renal targeting...
  78. ncbi Access to tetrachlorophthalimide-protected ethyl 2-amino-2-deoxy-1-thio-beta-D-glucopyranosides
    L Olsson
    Natural Products and Glycotechnology Research Institute, Durham, NC 27707, USA
    Carbohydr Res 314:273-6. 1998
    ..This was necessary because conditions normally used for beta-1-acetate formation were not tolerated by the tetrachlorophthalimido (TCP) group...
  79. ncbi Structural requirements for alkylglycoside-type renal targeting vector
    K Suzuki
    Pharmaceutical Research Center, Meiji Seika Kaisha, Ltd, Yokohama shi, Kanagawa, Japan
    Pharm Res 16:1026-34. 1999
    ..Thus, "alkylglycoside" is considered to be a novel targeting vector for the kidney (1,2). The present study is designed to clarify the structural requirements for alkylglycoside as a renal targeting vector...
  80. ncbi Properties of H(+)-ATPase from rat liver lysosomes as revealed by reconstitution into proteoliposomes
    M Okamoto
    Department of Biochemistry, Faculty of Pharmaceutical Sciences, Kanazawa University
    J Biochem 120:608-15. 1996
    ..It was inhibited by sulfate, sulfite, and thiocyanate from outside the vesicles, and by nitrate from both inside and outside the vesicles...
  81. ncbi Synthesis of 6-deoxy-5-thio-D-glucose
    E Bozó
    Institute for Drug Research, Budapest, Hungary
    Carbohydr Res 290:159-73. 1996
    ..The mechanism of this rearrangement is discussed in detail. The 6-mesylate 27 was converted via the 6-iodo derivative into the title compound...
  82. ncbi The myrosinase-glucosinolate interaction mechanism studied using some synthetic competitive inhibitors
    R Iori
    Istituto Sperimentale per le Colture Industriali, Bologna, Italy
    FEBS Lett 385:87-90. 1996
    ..Finally, 2d-GTL was shown to be the first strong competitive inhibitor of myrosinase ever reported...
  83. ncbi Purification of a membrane glycoprotein with an inositol-containing phospholipid anchor from Dictyostelium discoideum
    Z C Ti
    School of Biological Sciences, Macquarie University, Sydney, Australia
    J Biotechnol 16:233-43. 1990
    ..The purification strategy provides a means of purifying other GPI proteins, including those produced by protein engineering techniques...
  84. ncbi Changes in differently processed soya bean (Glycine max.) and lima bean (Phaseolus lunatus) with particular reference to their chemical composition and their mineral and some inherent anti-nutritional constituents
    V A Aletor
    Department of Animal Production and Health, Federal University of Technology, Akure, Nigeria
    Nahrung 33:1009-16. 1989
    ..The need to prevent both functional and nutritional damage to food proteins and other nutrients, resulting from excessive heating, was discussed...
  85. ncbi Compositional evaluation of some cowpea varieties and some under-utilized edible legumes in Nigeria
    V A Aletor
    Department of Animal Production and Health, Federal University of Technology, Akure, Nigeria
    Nahrung 33:999-1007. 1989
    ..9% for the cowpea varieties and the other legumes. The cowpea varieties generally had higher levels of thioglucosides, trypsin inhibitor activity (TIA) and lower haemagglutinating activity (mean values of thioglucosides: 3...
  86. ncbi Glucolimnanthin, a plant glucosinolate, increases the metabolism and DNA binding of benzo[a]pyrene in hamster embryo cell cultures
    W M Baird
    Department of Medicinal Chemistry and Pharmacognosy, Purdue University, West Lafayette, IN 47907
    Carcinogenesis 9:657-60. 1988
    ..These results indicate that the glucosinolate glucolimnanthin can increase the metabolic activation of B[a]P in mammalian cells in culture...
  87. ncbi Purin-6-yl 6-deoxy-1-thio-beta-D-glucopyranoside. Enzymology, chemistry, and cytotoxicity
    C K Zercher
    Department of Medicinal Chemistry, State University of New York, Buffalo 14260
    Carbohydr Res 165:299-305. 1987
    ..The 6-deoxyglucoside is more active than the D-glucosiduronic acid in an L1210 mouse screen...
  88. ncbi Mechanism of the enhancement effect of n-octyl-beta-D-thioglucoside on the transdermal penetration of fluorescein isothiocyanate-labeled dextrans and the molecular weight dependence of water-soluble penetrants through stripped skin
    T Ogiso
    Faculty of Pharmaceutical Sciences, Kinki University, Osaka, Japan
    J Pharm Sci 83:1676-81. 1994
    ..997, p < 0.001). However, the viable epidermis and dermis restricted the penetration of macromolecules, such as FD-70...
  89. ncbi Synthesis of a thio analogue of n-propyl kojibioside, a potential glucosidase inhibitor
    J S Andrews
    Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada
    Carbohydr Res 270:51-62. 1995
    ..3 mixture if the alpha and beta disaccharides (9 and 10); evidence is presented for the occurrence of the orthoester 11, as an intermediate in the formation of the beta-disaccharide...
  90. ncbi [Effects of thioglucoside on thyroid and iodine metabolism]
    B Q Jin
    Institute of Food and Feed Jiangsu Provincial Academy of Agricultural Sciences, Nanjing
    Zhonghua Yu Fang Yi Xue Za Zhi 28:333-6. 1994
    ..If iodine was supplied in the fodder and the antidotes were administered, the morphology and ultrastructure of the thyroid tissues in swine restored to normal, and their T4 and ratio of T4 to T3 tended to be normal, too...
  91. ncbi Optimization of glucosinolate separation by micellar electrokinetic capillary chromatography using a Doehlert's experimental design
    L Paugam
    Laboratoire de Microbiologie et Sécurité Alimentaire, Technopole Brest Iroise, Plouzane, France
    J Chromatogr A 864:155-62. 1999
    ..This method was validated by a statistical analysis and showed good linearity, repeatability and reproducibility...
  92. ncbi Fe(II)/Cu(I)-dependent P-type ATPase activity in the liver of Long-Evans cinnamon rats
    Kazuo Takeda
    Department of Molecular Cell Biology, University of Occupational and Environmental Health, Kitakyushu, 807 8555, Japan
    Life Sci 76:2203-9. 2005
    ..On the basis of these results, together with the similarity in optimal conditions required for full activity of the enzyme, we conclude that the Fe(II)-dependent ATPase (H-type) and WNDP may be identical...
  93. ncbi Chiral separation of amino acids by capillary electrophoresis with octyl-beta-thioglucopyranoside as chiral selector
    Chieu D Tran
    Department of Chemistry, Marquette University, PO Box 1881, Milwaukee, WI 53201, USA
    J Chromatogr A 978:221-30. 2002
    ..All amino acids were baseline separated with this OTG-SDS-CD system at optimal conditions...
  94. ncbi Analysis of urinary N-acetyl-beta-D-glucosaminidase using 2,4-dinitrophenyl-1-thio N-acetyl-beta-D-glucosaminide as the substrate
    Magohei Yamada
    International Reagents Company, Ltd, Kobe, Japan
    J Clin Lab Anal 17:127-31. 2003
    ..The optimum pH for the absorbance of p-nitrophenol and 2-chloro-4-nitrophenol does not match that for the enzyme reaction...
  95. ncbi ATP hydrolytic activity of an iron-stimulated P-type ATPase of mouse liver microsomes
    K Takeda
    Division of Molecular Cell Biology, School of Medicine, University of Occupational and Environmental Health, Japan, Yahatanishi ku, Kitakyushu 807 8555, Japan
    J UOEH 22:317-24. 2000
    ..Vanadate inhibited the iron-stimulated ATPase activity. These results suggest that microsomes from mouse liver contain the Fe(2+)-stimulated P-type ATPase...
  96. ncbi Glycosidase-catalyzed deoxy oligosaccharide synthesis. Practical synthesis of monodeoxy analogs of ethyl beta-thioisomaltoside using Aspergillus niger alpha-glucosidase
    Toshiyuki Nishio
    Laboratory of Bio organic Chemistry, College of Bioresource Sciences, Nihon University, 1866 Kameino, Fujisawa shi, Kanagawa 252 8510, Japan
    Biosci Biotechnol Biochem 67:1024-9. 2003
    ..0% isolated yield (based on 3D-Glc alpha-O-pNP). Products were not obtained from the enzymatic reactions between 4D- or 6D-Glc alpha-O-pNP and Glc beta-S-Et...
  97. ncbi Liposomes composed of reconstituted membranes for induction of tumor-specific immunity
    Larry E Westerman
    VGS DVRD NCID, Centers for Disease Control and Prevention, Atlanta, Georgia 30322, USA
    Methods Enzymol 373:118-27. 2003
  98. ncbi In vitro digestion of sinigrin and glucotropaeolin by single strains of Bifidobacterium and identification of the digestive products
    D L Cheng
    Department of Bioproductive Sciences, Utsunomiya University, 350 Minemachi, Utsunomiya, 321 8505 Japan
    Food Chem Toxicol 42:351-7. 2004
    ..AITC and benzyl isothiocyanate (BzITC) were barely detectable in the broth. It was concluded that the three species of Bifidobacteria could be involved in digestive degradation of glucosinolates in the human intestinal tract...
  99. ncbi Comparative evaluation of D-glucosyl thiouronium, glucosylthio heterocycles, Daonil, and insulin as inhibitors for hepatic glycosidases
    Olfat M El din Awad
    Department of Biochemistry, Faculty of Science, Alexandria University, Alexandria 21321, Egypt
    Carbohydr Res 339:469-76. 2004
    ..Compound 1 inhibited both alpha- and beta-glucosidases, but the inhibition was more potent with the beta-enzyme. Compound 2 was found to be a weaker inhibitor of these enzymes, while compound 3 showed a slight apparent activation...
  100. pmc Selective transport systems mediate sequestration of plant glucosides in leaf beetles: a molecular basis for adaptation and evolution
    Jürgen Kuhn
    Bioorganic Chemistry, Max Planck Institute for Chemical Ecology, Hans Knoll Strasse 8, D 07745 Jena, Germany
    Proc Natl Acad Sci U S A 101:13808-13. 2004
    ..vitellinae), we studied the molecular basis of sequestration by feeding the larvae structurally different thioglucosides resembling natural O-glucosides...
  101. pmc The Arabidopsis epithiospecifier protein promotes the hydrolysis of glucosinolates to nitriles and influences Trichoplusia ni herbivory
    V Lambrix
    Department of Genetics and Evolution, Max Planck Institute for Chemical Ecology, Carl Zeiss Promenade 10, D 07745 Jena, Germany
    Plant Cell 13:2793-807. 2001
    Glucosinolates are anionic thioglucosides that have become one of the most frequently studied groups of defensive metabolites in plants...

Research Grants2

  1. Hybrid triple quadrupole linear ion trap mass spectrometer
    Jan Stevens; Fiscal Year: 2006
    ..unreadable] [unreadable]..
  2. Ascorbylation of Oxidized Lipids and Atherosclerosis
    Jan Frederik Stevens; Fiscal Year: 2010
    ..This project contributes to our long- term goal to determine the role of lipid peroxidation in inflammatory and age-related disease and how its effects can be modulated by therapeutic or dietary intervention. ..