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  • 1
    ISSN: 0170-2041
    Keywords: Affinity labelling ; Epoxides ; β-Hexosaminidases ; Thioglycosides ; Enzymes ; Carbohydrates ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Irreversible Deactivation of Human β-Hexosaminidase A with the Alkylating Pseudodisaccharide (3,4,6/5)-6-(2-Acetamido-2-deoxy-β-D-glucopyranosylthio) -3,4-epoxy-5-hydroxycyclohexene(3,4,6/5)-6-(2-Acetamido-2-deoxy-β-D-glucopyranosylthio)-3,4-epoxy-5-hydroxycyclohexene (8b) has been synthesised and found to deactivate irreversibly human β-D-hexosaminidase from lysosomes. Deactivation did not take place in the presence of the competitive inhibitor (3,6/4,5)-6-(2-acetamido-2-deoxy-β-D-glucopyranosylthio)-4-bromo-3,5-dihydroxy-cyclohexene (5a/b).
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 419-426 
    ISSN: 0170-2041
    Keywords: Sphingosines ; Azidosphingosines ; Octadec-4-enes ; Enzymes ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Treatment of 2,4-O-benzylidene-D-threose (3) with the Wittig reagent obtained from 2-bromopentadecane furnished 5-methyloctadec-4-ene derivatives (E,Z)-8. The introduction of the azido group into the 2-position and acid-catalyzed removal of the benzylidene protective group afforded 5-methyl-substituted azidosphingosines (E)-10 and (Z)-10 which were converted via azide reduction into the corresponding sphingosines (E)-1 and (Z)-1, respectively. Reaction of 3 with methylmagnesium bromide, ensuing selective 2-O-mesylation, and then 4-O-oxidation gave ketone 13. The Wittig reaction of 13 with triphenyltetradecylphosphorane afforded exclusively 4-methyloctadec-4-ene derivative (Z)-16 which was transformed into 4-methyl-substituted sphingosine (Z)-2 as described above. For the synthesis of the corresponding E isomer, 3 was converted into carbinols 21h,l. 2-O-Silyl protection and then water elimination furnished 4-methyl-substituted (4E)-octadec-4-ene derivative (E)-23 which was transformed into (E)-2.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 16 (1977), S. 273-285 
    ISSN: 0570-0833
    Keywords: Sphingolipids ; Hereditary diseases ; Neurochemistry ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Sphingolipids are components of animal membranes that are made up of a hydrophobic ceramide and a hydrophilic moiety (phosphorylcholine, oligosaccharides or their derivatives). Several enzymes are required for the step-by-step degradation of the sphingolipids. If one of these enzymes is deficient or totally lacking, then its substrates accumulate in the body and cause severe damage, especially when storage occurs in the nervous system. The enzyme defects are inherited in a recessive manner.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
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