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  • 1
    Electronic Resource
    Electronic Resource
    Synthese von L-Prolin-haltigen O-Glycopeptiden (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 719-739 
    Details
    ISSN: 0170-2041
    Keywords: Glycopeptide synthesis ; Mucin ; O-Glycoproteins ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of L-Proline-Containing O-GlycopeptidesThe synthesis of a number of L-proline-containing O-glycopeptides in which 2-acetamido-2-deoxy-α-D-galacto-pyranose is α-glycosidically linked to L-threonine is described. For N-terminal extension with amino acids the building block 3 is preferred. For C-terminal extension a new intermediate is developed, that includes the Aloc/tBu combination of protective groups which can be synthesized with high yield and stereoselectivity. The Aloc group shows a low steric hindrance and is very stable. Therefore, the carbohydrate-containing compound 68 can also be coupled C-terminally with low-reactive L-proline derivatives in good yields. The synthesized O-glycopeptides shall be used in the investigation of the dependence of the protein structure on the glycosyltransferase activity of the biosyntheses of mucins.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1990199001138
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  • 2
    Electronic Resource
    Electronic Resource
    Bausteine von Oligosacchariden, CII. Synthese von modifizierten Derivaten der 2-Acetamido-2-desoxy-D-galactose zur Untersuchung der Substratspezifität der Core-1-β3-Gal-Transferase und der Core-3-β3-GlcNAc-Transferase der Biosynthese von O-Glycoproteinen (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 735-745 
    Details
    ISSN: 0170-2041
    Keywords: Carbohydrates ; Galactose, 2-acetamido-2-deoxy-D- ; O-Glycoproteins ; Glycosyltransferases ; Enzymes ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Building Units of Oligosaccharides, CII. - Synthesis of Modified Derivatives of 2-Acetamido-2-deoxy-D-galactose for the Examination of Substrate Specificities of Core 1-β3-Gal-Transferase and Core 3-β3-GlcNAc-Transferase Involved in the Biosynthesis of O-GlycoproteinsThe 2-, 3-, 4-, and 6-deoxy derivatives of benzyl 2-acetamido-2-deoxy-α-D-galactopyranoside (7) have been synthesized to test substrate specificities of glycosyltransferases involved in the biosynthesis of O-glycoproteins. The core 1-β3-Gal-transferase dose not require the 6-hydroxyl group for activity in contrast to the glycosylation reaction of the core 3-β3-GlcNAc-transferase which requires the 6-hydroxyl group. Compounds with reactive groups substituting the 6-hydroxyl group such as the diazirine 45 could be suitable for photolabeling of the former enzyme. A column for affinity chromatography with the 6-deoxy derivative as the ligand could be useful to separate the two enzymes during purification.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1992199201124
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  • 3
    Electronic Resource
    Electronic Resource
    Bausteine von Oligosacchariden, CIII. Synthese von modifizierten Derivaten des Disaccharides β-D-Gal-(1 → 3)-α-D-GalNAc zur Untersuchung der Substratspezifität der Core-2-β6-GlcNAc-Transferase und α-3-Sialyltransferase der Biosynthese von O-Glycoproteinen (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 747-758 
    Details
    ISSN: 0170-2041
    Keywords: Carbohydrates ; Oligosaccharides ; Glycosyltransferases ; O-Glycoproteins ; Enzymes ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Building Units of Oligosaccharides, CIII.  -  Synthesis of Modified Derivatives of the Disaccharide β-D-Gal-(→3)-α-D-GalNAc for the Examination of Substrate Specificities of Core 2-β6-GlcNAc-Transferase and α-3-Sialyltransferase Involved in the Biosynthesis of O-GlycoproteinsDerivatives of benzyl β-D-galactopyranosyl-(1→3)-2-acet-amido-2-deoxy-α-D-galactopyranoside have been synthesized. The 6′-, 4′- and 3′-OH group of the galactose moiety as well as the 6- and 4-OH and the 2-acetamido group of the 2-acet-amido-2-deoxy-D-galactose moiety have been selectively substituted by the corresponding deoxy function. The compounds are useful in studies of the substrate specificities of the core 2-β6-GlcNAc-transferase and the α3-sialyltransferase involved in the biosynthesis of O-glycoproteins.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1992199201125
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    Paper (German National Licenses)
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