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  • Carbohydrates  (6)
  • Catalytic antibodies  (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
    Synthesis of Highly Functionalised Carbohydrate-Derived Spiroacetals by Ring-Closing Metathesis and Pauson-Khand Reaction of Ketoglycosidic Enynes (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 873-877 
    Details
    ISSN: 1434-193X
    Keywords: Spiro compounds ; Ring-closing metathesis ; Pauson-Khand reaction ; Carbohydrates ; Enynes ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---The synthesis of the ketoglycosidic enynes 5, 7 and 8 starting from 2,3,4,6-tetra-O-benzyl-D-glucopyranolactone (2) is described. These enynes are subjected to ruthenium-mediated ring-closing metathesis and Pauson-Khand cyclisation to afford the highly functionalised carbohydrate spiroacetals 9 and 11-14.
    Type of Medium: Electronic Resource
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  • 3
    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
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  • 4
    Electronic Resource
    Electronic Resource
    Synthesis of Verbascoside: A Dihydroxyphenylethyl Glycoside with Diverse Bioactivity (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 2623-2632 
    Details
    ISSN: 1434-193X
    Keywords: Caffeic acid ; Carbohydrates ; Glycosidations ; Orthoester ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: TMSOTf-mediated condensation of ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside (2) with peracetylated α-L-rhamnopyranosyl trichloroacetimidate donor 3a resulted in the formation of orthoester 4, which, after acetylation, rearranged into ethyl 3-O-(α-L-rhamnopyranosyl)-1-thio-β-D-glucopyranoside derivative 6a. The latter compound was converted into the corresponding trichloroacetimidate donors 8a-b. An alternative approach to trichloroacetimidate 8c commenced with the iodonium ion mediated glycosidation of ethyl 2,3,4-tri-O-benzoyl-1-thio-α-L-rhamnopyranside (15) with 1,2:5,6-diisopropylidene-D-glucofuranose (16) to afford disaccharide 17, which was transformed into 8c in five steps. Condensation of 8a-c with 2-[3,4-di-(tert-butyldimethyl-silyloxy)phenyl]ethanol (12) gave, after deacylation, key intermediate 14. Protecting-group manipulation of 14 and subsequent esterification of resulting 22 with 3,4-di-O-tert-butyldimethylsilylcaffeic acid (27) gave, after deprotection, verbascoside (1).
    Additional Material: 1 Ill.
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  • 5
    Electronic Resource
    Electronic Resource
    Enzymatic Cleavage of N-Phenylacetyl-Protected Ethanolamine Phosphates (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 1215-1220 
    Details
    ISSN: 0947-3440
    Keywords: L-glycero-α-D-manno-Heptopyranosides ; Ethanolamine phosphates ; Phenylacetyl, enzymatic cleavage of ; Carbohydrates ; Glucosylations ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Immobilized penicillin-G acylase mediated removal of the N-phenylacetyl protective group in ethanolamine phosphates 7 and 9 furnished compounds 8 and 10, respectively. Deblocking of N-phenylacetyl-protected ethanolamine phosphate heptosyl disaccharide 22, a protected spacer-containing fragment of the inner-core lipopolysaccharide region of Neisseria meningitidis, immunotype L3 was readily accomplished with penicillin-G acylase, yielding target dimer 2. Disaccharide 22 was accessible by elongation of ethyl 1-thio-L-glycero-α-D-manno-heptopyranosyl donor 13 with acceptor 14 under the influence of N-iodosuccinimide/triflic acid. Protective group manipulations, phosphorylation with the reagent 2-cyanoethyl 2-(phenylacetylamino)ethyl N,N-diisopropylphosphoramidite (5) and deprotection furnished LD-Hepp dimer 22.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970625
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  • 6
    Electronic Resource
    Electronic Resource
    An Efficient Synthesis of (R)-3-{(R)-3-[2-O-(α-L-Rhamnopyranosyl)- α-L-rhamnopyranosyl] oxydecanoyl}oxydecanoic Acid, a Rhamnolipid from Pseudomonas Aeruginosa (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 303-307 
    Details
    ISSN: 1434-193X
    Keywords: Pseudomonas aeruginosa ; Rhamnolipid ; One-pot two-step glycosylation ; Chemoselectivity ; Esterification ; Carbohydrates ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: N-iodosuccinimide/triflic acid mediated one-pot two-step glycosylation of ethyl 2,3,4-tri-O-benzyl-1-thio-α-L-rhamnopyranoside (8) with phenyl 3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-α-L-rhamnopyranoside (10b) and phenacyl (R)-3-hydroxydecanoate (13) gave rhamnolipid 17. The latter was transformed in five steps into the title compound 2. Esterification of 2 with diazomethane resulted into the corresponding methyl ester derivative 1.
    Type of Medium: Electronic Resource
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  • 7
    Electronic Resource
    Electronic Resource
    Synthesis of Tetrameric Arabinogalactans Based on 1,2-Anhydrosugars (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 91-97 
    Details
    ISSN: 1434-193X
    Keywords: Carbohydrates ; Glycals ; Arabinogalactans ; 1,2-Anhydrosugars ; Monoclonal antibodies ; CCRC-M7 ; Thioethyl furanosides ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The spacer-containing tetrameric arabinogalactans 1-3, suitable for CCRC-M7 epitope characterization, are readily accessible by ZnCl2-assisted stepwise elongation of 11-methoxycarbonylundecanol 9 with the 1,2-anhydrogalactose building unit 6. NIS/cat. TfOH-mediated glycosylation of the newly formed 2-OH, 2′-OH, or 2′′-OH function in the β-(1→6)-galactoside backbone with the 1-thioarabinofuranoside donor 8, followed by deprotection, provided the target tetramers in high overall yield.
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