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  • 1
    Electronic Resource
    Electronic Resource
    Bausteine von Oligosacchariden, CX. Synthese von potentiellen Inhibitoren für die N-Acetylglucosaminyltransferase I (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 67-76 
    Details
    ISSN: 0947-3440
    Keywords: Carbohydrates ; Saccharides ; Trichloroacetimidates ; Glycosyltransferases ; Enzymes ; Transferases ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Building Units of Oligosaccharides, CX.  -  Synthesis of Potential Inhibitors of N-Acetylglucosaminyltransferase IModified derivatives of the trisaccharide octyl α-D-Man-(1→3)-[α-D-Man(1→6)]-β-D-Man were synthesized by attaching reactive groups via a pentyl spacer to the 4′-OH and 6′-OH group. Glycosylation steps were carried out by using the trichloroacetimidate method with suitable building blocks. The compounds substituted at 6′-OH are of special interest. The epoxide 27 and the diazirine 25 are reversible inhibitors of N-acetylglucosaminyltransferase I (GlcNAc-T I). Product 26 with a spacer-linked iodoacetamide is an irreversible inhibitor of GlcNAc-T I.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199519950110
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  • 2
    Electronic Resource
    Electronic Resource
    Bausteine von Oligosacchariden, CIX. Synthese von modifizierten Oligosacchariden der N-Glycoproteine zur Untersuchung der Substratspezifität der N-Acetylglucosaminyltransferase I (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 53-66 
    Details
    ISSN: 0947-3440
    Keywords: Carbohydrates ; Saccharides ; Glycosyltransferases ; Trichloroacetimidates ; Transferases ; Enzymes ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Building Units of Oligosaccharides, CIX.  -  Synthesis of Modified Oligosaccharides of N-Glycoproteins for Substrate Specificity Studies of N-Acetylglucosaminyltransferase IA series of modified derivatives of the trisaccharide octyl α-D-Man(1→3)-[α-D-Man(1→6)]-β-D-Man were synthesized for substrate specificity studies of N-acetylglucosaminyltransferase I (GlcNAc-T I). The hydroxyl groups at C-3, C-4 and C-6 of the α(1→3)-linked Mannose were replaced by hydrogen and methoxy groups. At the α(1→6)-linked mannose the hydroxyl group at C-2 was deoxygenated and the hydroxyl groups at C-3, C-4 and C-6 were replaced by methoxy groups. The syntheses of the ten trisaccharides were carried out by the interchangeable combination of modified building blocks. The trichloroacetimidate method was favourable for all glycosylation steps.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199519950109
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  • 3
    Electronic Resource
    Electronic Resource
    Bausteine von Oligosacchariden, CVII - Synthese von modifizierten Oligosacchariden der N-Glycoproteine zur Untersuchung der Substratspezifität der N-Acetylglucosaminyltransferase II (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 721-735 
    Details
    ISSN: 0170-2041
    Keywords: Carbohydrates ; Oligosaccharides ; Saccharides ; Glycoproteins ; Glycosyltransferase ; Transferases ; Enzymes ; Proteins ; Trichloroacetimidates ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Building Units of Oligosaccharides, CVII. - Synthesis of Modified Oligosaccharides of N-Glycoproteins for Substrate Specificity Studies of N-Acetylglucosaminyltransferase IISeveral modified derivatives of the tetrasaccharide β-D-GlcNAc-(1→2)-α-D-Man-(1→3)-[α-D-Man-(1→6)]-β-D-Man-octyl (1) were synthesized for substrate specifity studies of N-acetylglucosaminyltransferase II (GlcNAcT II). The hydroxyl groups at C-3, C-4 or C-6 of the α(1→6)-linked Man residue and the hydroxyl groups at C-3 and C-6 of the α(1→3)-linked Man were replaced by deoxy groups. All five tetrasaccharides were synthesized by a block synthesis by using deoxy saccharide residues. The trichloroacetimidate method was particulary successful for synthesizing the glycosidic linkages. The modified compounds have been tested as substrates for N-acetylglucosaminyltransferase II (GlcNAcT II) from rat liver. The substrate specificity of GlcNAcT II will be discussed.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1993199301118
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  • 4
    Electronic Resource
    Electronic Resource
    Bausteine von Oligosacchariden, CVIII. Synthese von modifizierten Oligosacchariden der N-Glycoproteine zur Untersuchung der Substratspezifitäten der N-Acetylglucosaminyltransferasen III bis VI (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 737-750 
    Details
    ISSN: 0170-2041
    Keywords: Carbohydrates ; Oligosaccharides ; Saccharides ; Glycoproteins ; Glycosyltransferase ; Transferases ; Enzymes ; Proteins ; Trichloroacetimidates ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Building Units of Oligosaccharides, CVIII. - Synthesis of Modified Oligosaccharides of N-Glycoproteins for Substrate Specificity Studies of N-Acetylglucosaminyltransferase III to VIThe pentasaccharide β-D-GlcNAc-(1→2)-α-D-Man-(1→3)-[β-D-GlcNAc-(1→2)-α-D-Man-(1→6)]-β-D-Man-octyl (3) and a series of modified derivatives of this compound were synthesized. The 4-OH group of the β-Man residue, the 3-OH or 4-OH group of the α-(1→3)-linked Man residue or the 6-OH group of the α(1→6)-linked Man residue were replaced by deoxy groups. The modified pentasaccharides were synthesized by a block synthesis using functionalized deoxy saccharide residues. Glycosylation reactions were achieved by the trichloroacetimidate method. These pentasaccharides are useful for substrate specificity studies of N-acetylglucosaminyltransferases III to VI (GlcNAcT III to VI). The substrate specificity of GlcNAcT V will be discussed since this activity has been found to be increased in malignancies.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1993199301119
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  • 5
    Electronic Resource
    Electronic Resource
    Bausteine von Oligosacchariden, CIV. Synthese von verzweigten Tetrasaccharid- und Pentasaccharid-Strukturen von N-Glycoproteinen, methyliert an 4′-OH des Verzweigungsgliedes (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 1303-1313 
    Details
    ISSN: 0170-2041
    Keywords: Carbohydrates ; Oligosaccharides ; Glycoproteins ; Transferases ; Enzymes ; Saccharides ; Trichloroacetimidates ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Building Units of Oligosaccharides, CIV.  -  Synthesis of Branched Tetrasaccharide and Pentasaccharide Structures of N-Glycoproteins Methylated at 4′-OH of the Branching UnitThe tetrasaccharide α-D-Manp-(1→3)[α-D-Manp-(1→6)]-4-O-methyl-β-D-Manp-(1→4)-D-GlcNAc (15) and the pentasaccharide β-D-GlcpNAc-(1→2)-α-D-Manp- (→3)[α-D-Manp-(→6)]-4-O-methyl-β-D-Manp- (→4)-D-GlcNAc (23) were synthesized by adding the respective functionalized building blocks. The compounds are useful for studies of the substrate specificities of GlcNAc transferases I and II in the biosynthesis of N-linked oligosaccharides, respectively. In addition we developed an effective synthesis for the β-glycosidically linked building block β-D-Manp-(→4)-α-D-GlcpNAc. The trichloroacetimidate method was particularly successful for synthesizing these glycosidic linkages.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1992199201215
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