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  • Catalytic antibodies  (1)
  • Double reductive amination  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Approach Toward a Generic Treatment of Gram-Negative Infections: Synthesis of Haptens for Catalytic Antibody Mediated Cleavage of the Interglycosidic Bond in Lipid A (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 2593-2600 
    Details
    ISSN: 1434-193X
    Keywords: Endotoxin ; Immunotherapy ; Catalytic antibodies ; Glycosidases ; Azasugars ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In order to develop a generic treatment for infections with Gram-negative bacteria, we developed a synthesis of 2-acylamino-deoxynojirimycin derivatives (17, 18, 19 and 20), which will be used as haptens for raising catalytic antibodies capable of hydrolyzing the interglycosidic bond in the lipid A moiety of endotoxins. A key intermediate in the preparation of compounds 17, 18, 19 and 20 is 3,4,6-tri-O-benzyl-2-[(benzyloxycarbonyl)amino]-2-deoxy-D-glucono-δ-lactam (6), which was prepared from known 3,4,6-tri-O-benzyl-2-[(benzyloxycarbonyl)amino]-2-deoxy-D-glucosamine (1) in four steps in 47% overall yield. Antibodies were generated against 2-[(6-aminohexanoyl)amino]-2-deoxy-D-glucono-δ-lactam (17) coupled to the carrier protein bovine serum albumin.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 2
    Electronic Resource
    Electronic Resource
    A Short and Flexible Route to Aza-β-(1→6)-C-disaccharides: Selective α-Glycosidase Inhibitors (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 1185-1189 
    Details
    ISSN: 1434-193X
    Keywords: Carbohydrates ; Aza sugars ; Double reductive amination ; Enzyme inhibitors ; Glycosidase inhibitors ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The syntheses of azaMan-β-(1→6)-C-Glc (4), azaGlc-β-(1→6)-C-Glc (5), and azaGal-β-(1→6)-C-Glc (6) based upon double reductive amination of acetylenic carbohydrate-derived diketones is described. The required diketones are obtained by addition of the acetylenic sugar anion derived from dibromoolefin 7 to benzyl-protected mannopyranolactone, glucopyranolactone, or galactopyranolactone, followed by reduction of the ketose and oxidation of the resulting diol. Ensuing double reductive amination and hydrogenolysis affords the target compounds in reasonable to good yields. Enzyme inhibition tests show that neither of the three compounds 4, 5, and 6 inhibit β-glycosidases, while moderate to good inhibitory activities were found on α-glycosidases, the most active being 6 (α-galactosidase: Ki = 0.092 μM).
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    Location Call Number Limitation Availability
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    Paper (German National Licenses)
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