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  • Pseudosugars  (4)
  • Arsenic  (3)
  • Wiley-Blackwell  (7)
  • American Institute of Physics (AIP)
  • 1
    Electronic Resource
    Electronic Resource
    Pseudosugars, 35. Synthesis of glycosylceramide analogs composed of imino-linked unsaturated 5a-carbaglycosyl residues: Potent and specific gluco- and galactocerebrosidase inhibitors (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 279-284 
    Details
    ISSN: 0947-3440
    Keywords: Carbohydrates ; Pseudosugars ; Cyclitols ; Glycolipid analogs ; Lipids, cyclitol ; Glycosylceramides, 5a-carba- ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 5a-Carba-β-glucosyl- E-3 and galactosylceramide analogs E-4 were synthesized by coupling of the protected derivatives 5 of β-valienamine and 15 of 4-epi-β-valienamine with the aziridines E-6 and Z-6, as the sphingosine precursors, respectively, and subsequent deprotection and N-acylation. Both the new analogs and their corresponding Z-isomers Z-3 and Z-4 were shown to be very potent and specific gluco- and galactocerebrosidase inhibitors, and, interestingly, the Z-isomers possess inhibitory activity comparable to that of the corresponding E-isomers.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199519950237
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  • 2
    Electronic Resource
    Electronic Resource
    Pseudosugars, 34. Synthesis of 5a-carba-β-D-glycosylceramide analogs linked by imino, ether and sulfide bridges (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 267-277 
    Details
    ISSN: 0947-3440
    Keywords: Carbohydrates ; Pseudosugars ; Cyclitols ; Glycoceramide analogs ; Lipids ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Carbocyclic analogs of glycoceramides, (2S,3R,4E)-1-(5a-carba-β-D-glycopyranosyl)-2-(hexadecanoylamino)-4-octa-decen-3-ols E-3-E-6, linked by imino, ether and sulfide bridges, were synthesized by coupling of aziridines, as the sphingosine precursors, with protected 1-amino, 1-hydroxy and 1-mercapto derivatives of 5a-carba sugars and subsequent deprotection and N-acylation. Biological assay of 5a-carbaglycosylceramides showed that both imino-linked E-3 and E-4 having gluco and galacto configurations are mild immunomodulators and possess a mild inhibitory activity against gluco- and galactocerebrosidases. These findings prompted us to prepare the corresponding Z-isomers Z-3 and Z-4, which interestingly show a similar enzyme-inhibitory activity.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199519950236
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  • 3
    Electronic Resource
    Electronic Resource
    Pseudosugars, 33. Synthesis of some 5a-carbaglycosylamides, glycolipid analogs of biological interests (1994)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1994 (1994), S. 103-107 
    Details
    ISSN: 0170-2041
    Keywords: Carbohydrates ; Pseudosugars ; Cyclitols ; Glycolipid analogs ; Lipids, cyclitol ; Glycosylamides, 5a-carba- ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Five carbocyclic analogs of glycosylamides, N-(5a-carba-D-glycopyranosyl)-N-octadecyldodecanamides 2-6, having β-galacto, α- and β-gluco-, and α- and β-manno configurations, were synthesized by coupling of the protected anhydro derivatives 12, 15, and 21 of 5a-carba-sugars with octadecylamine, followed by N-acylation. Walden inversion of the 2-OH functions of 17 and 24 was carried out through O-sulfonylation. A bioassay (in vivo) of 5a-carbaglycosylamides showed that they are potent immunomodulators, obviously comparable to the true sugar analogs, suggesting that the 5acarbasugar analogs may provide appropriate model compounds for biochemical studies in glycolipid chemistry.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199419940202
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  • 4
    Electronic Resource
    Electronic Resource
    Historical cohort studies in three arsenic poisoning areas in japan (1992)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 6 (1992), S. 333-341 
    Details
    ISSN: 0268-2605
    Keywords: Arsenic ; exposure cancer ; standardized mortality rate ratio ; epidemiology ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The results of historical cohort studies of three arsenic poisoning incidents in Japan are presented. The first episode was in a small mountainous community near an arsenic mine and refinery, at Toroku, where patients with chronic arsenism were certified by application of the Pollution Health Damage Compensation Law. The second area was in a small town, Namiki-cho, near Nakajo-machi, where wells were poisoned by arsenic produced in an arsenic(III) sulfide factory. As to the third cohort, eight residents of Nishikawa-machi who ingested well-water suffered arsenic poisoning about 35 years ago. The standardized mortality ratios were used in analyzing these data. Excesses of cancer mortality, especially lung cancer, were observed among the subjects in these areas. In Japan, there are many arsenic poisoning episodes, involving for example soy-sauce poisoning, powdered-milk poisoning and other incidents associated with arsenic mines. Thus it is necessary to clarify the chronic effects of arsenic in these areas.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/aoc.590060405
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  • 5
    Electronic Resource
    Electronic Resource
    Comparisons of survival time estimates for niigata prefecture (japan) residents exposed to ingested arsenic (1994)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 8 (1994), S. 237-244 
    Details
    ISSN: 0268-2605
    Keywords: Arsenic ; environmental exposure ; Kaplan-Meier method ; lifetime survival ; life test analysis ; logrank test ; survival analysis ; survival time ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Survival analysis was used to analyze follow-up data on an arsenic-poisoned area, identified in 1959, in order to assess the effect of arsenic on survival time. The subjects were 443 residents of Namiki-cho, Nakajo-machi, Niigata Prefecture, Japan, who ingested well water contaminated with arsenic between 1955 and 1959. Their exposure to arsenic was only by ingestion of well water. We observed this historical cohort from October 1959 to February 1992. Survival time was calculated in two ways: from 1959 (the end of exposure) until death or until 1992 (the termination of follow-up); or from birth until death or until 1992. The entire cohort was divided into two groups according to the arsenic concentration measured in the wells in 1959. Different survival curves of the two were drawn using the Kaplan-Meier method. The lifetime survival curves indicate that the lifetimes of arsenic-exposed residents were significantly shorter than that of the low-dose exposure group or of unexposed residents. From the differences in the estimated lifetime survival curves, the effect of arsenic on the mortality of the residents can be inferred.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/aoc.590080313
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  • 6
    Electronic Resource
    Electronic Resource
    Did Arsenic Contamination in the Inagawa River Occur in Geogenic Relation to the Great Hanshin (Kobe) Earthquake of 1995? (1996)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 10 (1996), S. 757-760 
    Details
    ISSN: 0268-2605
    Keywords: Arsenic ; environmental standard ; river ; ground water ; earthquake ; Chemistry ; Industrial Chemistry and Chemical Engineering
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Arsenic contamination in river and ground water was investigated in the Inagawa area of Kansai district, Japan, from August to October, 1995. Arsenic has been continually detected at a level about 2 times higher than the environmental standard in the two tributaries of the Inagawa River, i.e. the Kimo and the Shio Rivers. The arsenic contamination was probably caused by the topographical change after the Great Hanshin Earthquake.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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  • 7
    Electronic Resource
    Electronic Resource
    Pseudosugars, 32. - Synthesis of 1,4-Imino-linked Carbadisaccharides Composed of a 2-Amino-5a-carba-2-deoxyglucopyranosylamine Residue and Its Congeners (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 755-769 
    Details
    ISSN: 0170-2041
    Keywords: Carbohydrates ; Pseudosugars ; Cyclitols ; Glucopyranose, 5a-carba- ; Acarviosin analogs ; Saccharides ; Carbasaccharides ; Carbaglucopyranoses ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Carbadisaccharide 5, containing a 2-acetamido-5a-carba-2-deoxyhexopyranosylamine residue, was synthesized by coupling of methyl 4-amino-4-deoxy-α-D-glucopyranoside (41) with the N-(2,4-dinitrophenyl)epimino compound 16 followed by deprotection. The 6′-acetamido-6′-deoxy analog 3 of a potent α-glucosidase inhibitor methyl acarviosin (1) was synthesized from a condensate 50 obtained by coupling of 41 with the protected epimino compound 18, possessing an exo-methylene function. This process involves a sequence of reactions: replacement by a benzoate ion and successive dehydrobromination of the dibromide 52 obtained from 50. Hydroxymercuration of 50 followed by demetalation and deprotection gave two carbadisaccharide analogs 7 and 9 containing the valiolamine-type branched aminocyclitol moieties. The free amines 4, 6, 8, and 10 were prepared by treatment of the corresponding N-protected derivatives with Amberlite IRA 400 (OH-) resin. Biological assays of all carbadisaccharides were carried out with three sugar hydrolases. Only compounds 6 and 8 were shown to be very weak α-mannosidase inhibitors. The introduction of the acetamido or amino function instead of the hydroxyl group into the C-6′ position of the methyl acarviosin analog 2 resulted in an appreciable decrease of the inhibitory activity.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1993199301121
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