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  • 1
    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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  • 2
    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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  • 3
    Electronic Resource
    Electronic Resource
    Pseudo-sugars, 31. New Synthesis of 2-Amino-5a-carba-2-deoxy-α-DL-glucopyranose and Its Transformation into Valienamine and Valiolamine Analogues (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 637-641 
    Details
    ISSN: 0170-2041
    Keywords: Carbohydrates ; Pseudo-sugars ; Cyclitols ; Glucopyranose, 5a-carba- ; Valienamine analogue ; Valiolamine analogue ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The positional isomers 2, 4, and 6 of respective validamine (1), valiolamine (3), and valienamine (5), derived from 2-amino-5a-carba-2-deoxy-α-D-glucopyranose, were synthesized as racemates from DL-(1,3/2,4,6)-3-acetamido-1,2-di-O-acetyl-4-bromo-6-bromomethyl-1,2-cyclohexanediol (8). Compounds 2, 4, and 6 showed very weak inhibitory activities against yeast α-D-glucosidase.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1992199201109
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  • 4
    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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  • 5
    Electronic Resource
    Electronic Resource
    Pseudo-sugars, 30. Synthesis of Amino-5a-carba-deoxyhexopyranoses from 2(3)-Acetoxy-5-acetoxymethyl-3(2)-p-toluenesulfonamido-7-oxabicyclo[2.2.1]heptanes (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 629-636 
    Details
    ISSN: 0170-2041
    Keywords: Carbohydrates ; Pseudo-sugars ; Cyclitols ; Hexopyranoses, 5a-carba- ; Bicyclo[2.2.1]heptanes, 7-oxa- ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: cis-Hydroxyamination of endo-2-acetoxymethyl-7-oxabicyclo[2.2.1]hept-5-ene (1) under Sharpless conditions affords two positional isomers 3 and 7 of 5-endo-acetoxymethyl-2(3)-exo-hydroxy-3(2)-exo-p-toluenesulfonamido-7-oxabicyclo[2.2.1]heptanes. Cleavage of the 1,4-anhydro ring of the corresponding acetyl derivatives 4 and 8 with 18% hydrogen bromide in acetic acid at 80°C produces several bromodeoxy aminocyclitol derivatives, from which, on hydrolysis or nucleophilic substitution with an acetate ion, the known 2-acet-amido-5a-carba-2-deoxy-α-DL-allo (25) and -gulopyranose tetraacetates (26), and new 3-acetamido-5a-carba-3-deoxy-α-DL-allopyranose tetraacetate (30) have been obtained. Likewise, the new 3-acetamido-5a-carba-3-deoxy-β-DL-talopyranose tetraacetate (39) has been prepared by starting from the exo-isomer 2.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1992199201108
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  • 6
    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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