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Thioglucosides (1):
Recent article
Thioglucosides
Abstract
In-vitro binding studies revealed that both tracers bind more effectively to tumour cells expressing the glucose transporter 1 rather than the glucose transporter 2, and this binding was specific for [F]FDG. Tc-TG shows the highest binding to bacteria and, in addition, gives the highest rate of accu...
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PMID: 20032803
PDF is available here.
PDF is available here.
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Abstract
We report the one-step transfer of the last three steps of the benzylglucosinolate pathway (comprising the C-S lyase, glycosyltransferase and sulfotransferase) from Arabidopsis to tobacco. This was achieved using an expression construct consisting of a single 2A polycistronic open reading frame, whi...
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PMID: 18830705
PDF is available here.
PDF is available here.
Biophysical Journal (94)9 2008
Abstract
The membrane protein bacteriorhodopsin (BR) can be kept soluble in its native state for months in the absence of detergent by amphipol (APol) A8-35, an amphiphilic polymer. After an actinic flash, A8-35-complexed BR undergoes a complete photocycle, with kinetics intermediate between that in detergen...
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PMID: 18192360
PDF is available here.
PDF is available here.
Abstract
We find that short OGA, which possesses O-GlcNAcase catalysis machinery like that of long OGA, exhibits comparative resistance to previously described potent inhibitors of long OGA and lysosomal hexosaminidases, including PUGNAc and NAG-thiazoline, suggesting a role for the HAT domain in O-GlcNAcase...
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PMID: 17994748
PDF is available here.
PDF is available here.
Abstract
Prostate weight was similar in rats treated with freeze-dried aqueous extract of red maca prepared after 2 and 3 hours of boiling. Freeze-dried aqueous extract of red maca, hydroalcoholic extract of red maca and finasteride reduced prostate weight in rats with prostatic hyperplasia. No difference wa...
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PMID: 17334591
PDF is available here.
PDF is available here.
Carbohydrate Research (341)17 2006
Abstract
To develop novel biologically active organic compounds possessing a sugar moiety, a series of 2-phenylsulfonylhydrazono-3-(2',3',4',6'-tetra-O-acetyl-beta-d-glucopyranosyl)thiazolidine-4-one were synthesized via reaction of the thiosemicarbazide with ethyl bromoacetate. Their chemical structures wer...
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PMID: 17027940
PDF is available here.
PDF is available here.
Carbohydrate Research (341)17 2006
Abstract
Three new 1-thioglycosides namely methylthiomethyl 1-thio-beta-D-glucopyranoside (Afrostyraxthioside A), methylsulfonylmethyl 1-thio-beta-D-glucopyranoside (Afrostyraxthioside B) and methylsulfonylmethylthiomethyl 1-thio-beta-D-glucopyranoside (Afrostyraxthioside C) were isolated from the seeds of A...
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PMID: 17054924
PDF is available here.
PDF is available here.
ChemBioChem (7)12 2006
Abstract
We show that P. rapae larvae convert benzylglucosinolate to phenylacetylglycine, which is released in their faeces. Feeding experiments with isotopic tracers suggest that phenylacetonitrile and phenylacetic acid are intermediates in this conversion. We also identified additional glycine and isoserin...
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PMID: 17086559
PDF is available here.
PDF is available here.
Abstract
n-Octyl-beta-D-glucopyranoside (OG) is a non-ionic glycolipid, which is used widely in biotechnical and biochemical applications. All-atom molecular dynamics simulations from two different initial coordinates and velocities in explicit solvent have been performed to characterize the structural behav...
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PMID: 16386443
PDF is available here.
PDF is available here.
Carbohydrate Research (341)10 2006
Abstract
The stereochemical outcome of glycosylation reactions with model thioglycosides and selenoglycosides proved to be dependent on the source of promoter iodonium ion, with iodine giving different results to N-iodosuccinimide (NIS) alone or N-iodosuccinimide/trimethylsilyltrifluoromethanesulfonate (NIS/...
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PMID: 16697999
PDF is available here.
PDF is available here.
Abstract
Abstract
The phase behavior and microstructure of aqueous mixtures of n-octyl-beta-D-glucoside (C8betaG1) and triethylene glycol mono-n-octyl ether (C8E3) is presented. C8betaG1 forms a one-phase micellar solution in water at surfactant concentrations up to 60 wt %, whereas mixtures with C8E3 show a liquid-l...
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PMID: 16229514
PDF is available here.
PDF is available here.
Abstract
Glycosylation reactions of 5-thioglucopyranosyl trichloroacetimidates bearing ethereal protective groups at the 2-O-position 14-15, and 37 proceed smoothly to give alpha-glycosides stereoselectively by using a catalytic amount of silyl triflate. This methodology allowed us to achieve syntheses of su...
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PMID: 15982892
PDF is available here.
PDF is available here.
Life Sciences (76)19 2005
Abstract
We conclude that the Fe(II)-dependent ATPase (H-type) and WNDP may be identical....
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PMID: 15733935
PDF is available here.
PDF is available here.
Abstract
We studied the molecular basis of sequestration by feeding the larvae structurally different thioglucosides resembling natural O-glucosides. Their accumulation in the defensive systems demonstrated that the larvae possess transport systems, which are evolutionarily adapted to the glycosides of their...
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PMID: 15365181
PDF is available here.
PDF is available here.
Journal of Biological Chemistry (279)35 2004
Abstract
We describe two crystal structures: the structure of antigen 85C co-crystallized with octylthioglucoside as substrate, resolved to 2.0 A, and the crystal structure of antigen 85A, which was solved at a resolution of 2.7 A. The structure of 85C with the substrate analog identifies residues directly i...
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PMID: 15192106
PDF is available here.
PDF is available here.
Abstract
Three strains of Bifidobacterium sp., B. pseudocatenulatum, B. adolescentis, and B. longum were studied for their ability to digest glucosinolates, sinigrin (SNG) and glucotropaeolin (GTL), in vitro. All strains digested both glucosinolates during 24-48 h cultivation, accompanied by a decline in the...
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PMID: 14871576
PDF is available here.
PDF is available here.
Carbohydrate Research (339)3 2004
Abstract
Comparison of the in vivo and in vitro effects of S-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)thiuronium bromide (1), 2-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylthio-1,3,4-thiadiazolin-5-thione (2), and 2-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylthio)-1,3-benzoxazole (3), as well as the...
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PMID: 15013383
PDF is available here.
PDF is available here.
Abstract
New acylated 5-thio-beta-D-glucopyranosylimino-disusbstituted 1,3,4-thiadiazols 8, and 11 were prepared, via spontaneous rearrangements, by cycloaddition of the glycosyl isothiocyanate 2 with the reactive intermediates 1-aza-2-azoniaallene hexachloroantimonates 4 and 6, respectively. Reaction of 2 w...
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PMID: 15598075
PDF is available here.
PDF is available here.
Clinical Science (105)5 2003
Abstract
We now report on some novel NO-donor drugs, based on thiosugars that generate NO spontaneously. From the range of compounds synthesized, D-SNAG ( S -nitroso-1-thio-2,3,4,6-tetra- O -acetyl-beta-D-glucopyranose) was as effective a vasodilator as any other and, as it was the easiest to synthesize, we...
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PMID: 12837129
PDF is available here.
PDF is available here.
Phytotherapy Research (17)6 2003
Abstract
We found that a crude extract from the roots of Lepidium virginicum exhibited antiprotozoal activity against Entamoeba histolytica trophozoites (IC(50) of 100.1 micro g/mL). Bioassay-guided fractionation resulted in the isolation of one known glucosinolate responsible for such activity. This compoun...
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PMID: 12820228
PDF is available here.
PDF is available here.
Abstract
Enzymatic transglycosylation using four possible monodeoxy analogs of p-nitrophenyl alpha-D-glucopyranoside (Glc alpha-O-pNP), modified at the C-2, C-3, C-4, and C-6 positions (2D-, 3D-, 4D-, and 6D-Glc alpha-O-pNP, respectively), as glycosyl donors and six equivalents of ethyl beta-D-thioglucopyran...
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PMID: 12834279
PDF is available here.
PDF is available here.
Journal of Plant Physiology (160)3 2003
Abstract
These results suggested that phototropic stimulation promotes myrosinase gene expression and myrosinase activity in the illuminated side, resulting in the conversion of inactive MTBG to active MTBI and simultaneously producing more active raphanusanins, causing a phototropic response....
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PMID: 12749082
PDF is available here.
PDF is available here.
Abstract
2,4-Dinitrophenyl-1-thio N-acetyl-beta-D-glucosaminide was examined as a new substrate for analyzing the level of N-acetyl-beta-D-glucosaminidase in the urine of patients suffering from renal diseases. The analysis is based on the fact that the substrate, when hydrolyzed in the presence of N-acetyl-...
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PMID: 12784261
PDF is available here.
PDF is available here.
Methods in Enzymology (373) 2003
Abstract
Journal of Chromatography A (978)1-2 2002
Abstract
1-S-Octyl-beta-D-thioglucopyranoside (OTG) was evaluated as a chiral selector for the separation of dansyl-amino acids by capillary electrophoresis. Enantiomeric separations of the amino acids can be accomplished by judiciously adjusting the pH of the solution and the concentration of OTG. Better se...
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PMID: 12458958
PDF is available here.
PDF is available here.
Carbohydrate Research (337)1 2002
Abstract
N-Bromosuccinimide (NBS) together with a catalytic amount of Me(3)SiOTf was found to be effective for the activation of thioglycosides. Concurrently with formation of the glycosidic bond, bromination took place on the activated aromatic ring of a 4-methoxyphenyl aglycon.
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PMID: 11755909
PDF is available here.
PDF is available here.
Abstract
One- and two-dimensional (1)H NMR spectroscopy were used to study the biotransformation of two dietary glucosinolates, sinigrin (SIN), and glucotropaeolin (GTL) by the human digestive microflora in vitro. The molecular structures of the new metabolites issued from the aglycone moiety of the glucosin...
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PMID: 11602519
PDF is available here.
PDF is available here.
Carcinogenesis (22)10 2001
Abstract
We investigated the impact of the intestinal microflora on the genotoxicity of 2-amino-3-methylimidazo[4,5-f] quinoline (IQ), a mutagenic/carcinogenic heterocyclic amine commonly found in fried meats and fish. In parallel, we also examined the effect of the microflora on the protective effect of glu...
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PMID: 11577015
PDF is available here.
PDF is available here.
Abstract
Screening for novel thioglucoside hydrolase activity resulted in the isolation of Sphingobacterium sp. strain OTG1 from enrichment cultures containing octylthioglucoside (OTG). OTG was hydrolysed into octanethiol and glucose by cell free extracts. Besides thioglucoside hydrolysis, several other gluc...
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PMID: 11601617
PDF is available here.
PDF is available here.
Carbohydrate Research (334)2 2001
Abstract
Treatment of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-beta-D-glucopyranose with 1,6-anhydro-3,4-dideoxy-2-O-p-toluenesulfonyl-beta-D-erythro-hex-3-enopyranose gave 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl-(1-->4)-1,6-anhydro-2,3-dideoxy-4-thio-beta-D-erythro-hex-2-enopyranos...
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PMID: 11502271
PDF is available here.
PDF is available here.
Biochemistry (Washington) (40)10 2001
Abstract
We now report, using simple esterification as well as acidolysis (triglycerides as substrates) as nonaqueous model reactions, that the presence of a detergent (n-octyl-beta-glucopyranoside) in the freeze-drying buffer, at concentrations below the critical micellar concentration, generates different...
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PMID: 11258933
PDF is available here.
PDF is available here.
YAKUGAKU ZASSHI (121)2 2001
Abstract
An extraction method based on the phase separation of aqueous micellar solutions of n-octyl-beta-D-thioglucoside (OTG) was applied to the concentrating conjugated bilirubin in urine. The analyte in sample solutions could be efficiently concentrated into a small volume of surfactant-rich phase, while...
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PMID: 11218735
PDF is available here.
PDF is available here.
Abstract
We report on the use of the detergent n-octyl beta-d-thioglucopyranoside in 2D crystallization trials of membrane proteins with radically different structures including FhuA from the outer membrane of Escherichia coli, light-harvesting complex II from Rubrivivax gelatinosus, and Photosystem I from c...
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PMID: 11356065
PDF is available here.
PDF is available here.
Zhongguo ji sheng chong xue yu ji sheng chong bing za zhi = Chinese journal of parasitology & parasitic diseases (19)5 2001
Abstract
Journal of UOEH (22)4 2000
Abstract
These results suggest that microsomes from mouse liver contain the Fe(2+)-stimulated P-type ATPase....
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PMID: 11132520
PDF is available here.
PDF is available here.
Biochemistry (Washington) (39)47 2000
Abstract
We have developed conditions for recording the low-frequency S(2)/S(1) Fourier transform infrared difference spectrum of hydrated PSII samples. By exchanging PSII samples with buffered (18)O water, we found that a positive band at 606 cm(-)(1) in the S(2)/S(1) spectrum in (16)O water is clearly down...
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PMID: 11087389
PDF is available here.
PDF is available here.
Analytical Biochemistry (285)2 2000
Abstract
We have determined the major ingredients of the commercially available reagents M-PER, Y-PER, and B-PER from Pierce Chemical Co. using electrospray mass spectrometry. These three proprietary reagents have been widely used in the biochemical community as cell membrane dissolving tools during the init...
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PMID: 11017703
PDF is available here.
PDF is available here.
Abstract
We investigated the chain elongation pathway for methionine that is involved in glucosinolate biosynthesis in Eruca sativa. Isotopically labeled methionine and acetate were administered to cut leaves and the major product, 4-methylthiobutylglucosinolate (isolated as its desulfated derivative), was a...
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PMID: 10860559
PDF is available here.
PDF is available here.
Abstract
A metabolically stable beta-N-acetylglucosaminyl-1-thio-N-Fmoc-serine (S-GlcNAc-Ser) derivative was synthesized in two procedures: one involving a coupling of a readily obtainable 1-pseudo-thiourea of GlcNAc (S-GlcNAc) and iodo-N-Boc-L-alanine benzyl ester, and the other utilizing a modified Mitsuno...
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PMID: 10866402
PDF is available here.
PDF is available here.
Biomaterials (21)12 2000
Abstract
Spoilage is a primary factor in the biocompatibility of soft contact lenses (SCL) within the lacrimal fluid. Tears are a complex mixture of proteins, lipids, natural surfactants and salts. The spoilation process is due to a contribution of all these components and of the nature of SCL materials them...
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PMID: 10811301
PDF is available here.
PDF is available here.
Phytochemistry (54)3 2000
Abstract
These results suggest that phototropic stimulation promotes myrosinase activity in the illuminated side of radish hypocotyls, releasing bioactive MTBI from inactive MTBG and simultaneously producing bioactive raphanusanins....
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PMID: 10870181
PDF is available here.
PDF is available here.
Journal of Chromatography A (879)2 2000
Abstract
An extraction method based on polymer-induced phase separation of aqueous micellar solutions of octyl-beta-D-thioglucoside (OTG) was assessed for concentrating hydrophobic analytes. Various hydrophobic compounds such as polycyclicaromatic hydrocarbons, alkylbenzenes, alkylphenols, chlorobenzenes, ch...
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PMID: 10893028
PDF is available here.
PDF is available here.
Journal of Biological Chemistry (275)19 2000
Abstract
We report cloning and characterization of cytochrome P450 CYP79A2 involved in aldoxime formation in the glucosinolate-producing Arabidopsis thaliana L. The CYP79A2 cDNA was cloned by polymerase chain reaction, and CYP79A2 was functionally expressed in Escherichia coli. Characterization of the recomb...
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PMID: 10799553
PDF is available here.
PDF is available here.
Abstract
Plants of Brassica napus were assessed quantitatively for their susceptibility to lateral root crack colonization by Azorhizobium caulinodans ORS571(pXLGD4) (a rhizobial strain carrying the lacZ reporter gene) and for the concentration of glucosinolates in their roots by high-pressure liquid chromat...
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PMID: 10788398
PDF is available here.
PDF is available here.
Abstract
These results indicate that p-NPbetaSglc is transported by the Na+/glucose cotransporter in small intestine. The order of turnover rate for glycoside transport by Na+/glucose cotransporter was 3-OMG > p-nitrophenyl beta-O-glucoside > p-NPbetaSglc > p-NPbetaSgal, indicating that the presence of a gal...
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PMID: 10757418
PDF is available here.
PDF is available here.
Carbohydrate Research (323)1-4 2000
Abstract
A novel pseudo-disaccharide having an imino sugar residue at the non-reducing end, namely, a sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide, which is a potential specific inhibitor for glycosidases that recognize not only the glycosidic linkage but also the aglycone moiety, was synthesized...
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PMID: 10782281
PDF is available here.
PDF is available here.
Journal of Chromatography A (864)1 1999
Abstract
The aim of this study was to optimize by micellar electrokinetic chromatography the separation of four glucosinolates, i.e. sinigrin, glucobrassicin and methoxyglucobrassicin involved in Cruciferae resistance mechanisms and glucotropaeolin used as an internal standard. The separation borate buffer w...
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PMID: 10630880
PDF is available here.
PDF is available here.
Allelochemicals released in soil following incorporation of rapeseed (Brassica napus) green manures.
Abstract
Plant-derived allelochemicals such as those produced by glucosinolate hydrolysis in Brassica napus, or rapeseed, are viable alternatives to synthetic compounds for the control of soil-borne plant pests. However, allelochemical production and residence times in field soils have not been determined. S...
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PMID: 10552731
PDF is available here.
PDF is available here.
Pharmaceutical Research (16)7 1999
Abstract
The structural requirements for the renal targeting vector have been identified to be as follows: a hydrophobic group (alkyl chain or aromatic ring) should be introduced to a sugar (D-glucose, D-mannose, or 2-deoxy-D-glucose) via a beta-glycoside binding atom (S > NH > O)....
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PMID: 10450926
PDF is available here.
PDF is available here.
Journal of Membrane Biology (170)1 1999
Abstract
These results suggest that microsomes from mouse liver contain copper/iron-stimulated P-type ATPase....
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PMID: 10398756
PDF is available here.
PDF is available here.
Abstract
These results indicate a role for indole glucosinolates and IAN/IAA in relation to symptom development in clubroot disease....
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PMID: 10384731
PDF is available here.
PDF is available here.
Abstract
We studied the inhibitory effects of glycosylated derivatives on the binding of [3H]Glc-O-C8-AVP [a glucosylated derivative of Arg8-vasopressin (AVP), Kd = 55 nM] to clarify the structural requirements necessary for renal recognition. Glc-S-C7-Me (octyl beta-D-thioglucoside) markedly inhibited the b...
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PMID: 9862753
PDF is available here.
PDF is available here.
Carbohydrate Research (314)3-4 1998
Abstract
Ethyl 2-deoxy-2-tetrachlorophthalimido-1-thio-beta-D-glucopyranoside (7) was prepared from glucosamine hydrochloride in four steps with a 20-25% overall yield. Formation of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-tetrachlorophthalimido-beta-D- glucopyranoside (5) was found to be crucial for this reaction s...
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PMID: 10335593
PDF is available here.
PDF is available here.
Biochemistry (Washington) (37)49 1998
Abstract
Comparisons of catalytic mechanisms have not previously been performed for homologous enzymes from hyperthermophilic and mesophilic sources. Here, the beta-glucosidase from the hyperthermophilic archaeon Pyrococcus furiosus was recombinantly produced in Escherichia coli and shown to have biophyscial...
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PMID: 9860830
PDF is available here.
PDF is available here.
Journal of Molecular Biology (283)2 1998
Abstract
We suggest that it is initiated by insertion of the detergent molecules into the membrane. At low temperature, the transformation into the vesicular structure is inhibited and no large crystal is produced directly from membrane/detergent/precipitant mixtures. When a suspension of the spherical vesic...
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PMID: 9769218
PDF is available here.
PDF is available here.
Phytochemistry (48)8 1998
Abstract
We have run the reaction under denaturing conditions. The results showed that the reaction of myoglobin with high concentrations of benzyl-ITC in the presence of 8 M urea led to a higher degree of derivatization than in the presence of water only. In addition, the Mr distribution of the reaction pro...
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PMID: 9720313
PDF is available here.
PDF is available here.
Abstract
The micellization process of bovine rod outer segment (ROS) membranes is investigated utilizing a series of neutral detergents. It is found that when alkyl(thio)glucosides with an appropriate hydrophillic-lipophilic balance (e.g. octylthioglucoside) are used in combination with a divalent cation, rh...
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PMID: 9613234
PDF is available here.
PDF is available here.
Biophysical Journal (74)3 1998
Abstract
We obtained vesicles from purple membrane of Halobacterium halobium at different suspension compositions (pH, electrolytes, buffers), following the procedure of Kouyama et al. (1994) (J. Mol. Biol. 236:990-994). The vesicles contained bacteriorhodopsin (bR) and halolipid, and spontaneously formed du...
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PMID: 9512037
PDF is available here.
PDF is available here.
Carbohydrate Research (304)3-4 1997
Abstract
Condensation of 5-thio-D-glucopyranose pentaacetate with 4-cyanobenzenethiol, in the presence of trimethylsilyl triflate, gave 4-cyanophenyl 2,3,4,6-tetra-O-acetyl-1,5-dithio-alpha-D-glucopyranoside 7 and 3,4,6-tri-O-acetyl-2,5-anhydro-5-thio-D-mannose bis(4-cyanophenyl) dithioacetal 9 in a 2:3 rati...
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PMID: 9468629
PDF is available here.
PDF is available here.