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  • Alzheimer's disease  (1)
  • Organic Chemistry  (1)
  • 1995-1999  (2)
  • 1
    Electronic Resource
    Electronic Resource
    Selective dimerization of cysteines in glycopeptides and phosphopeptides (1997)
    Springer
    International journal of peptide research and therapeutics 3 (1997), S. 371-377 
    Details
    ISSN: 1573-3904
    Keywords: Alzheimer's disease ; Disulfide bond formation ; Peptide ; Repeat domains ; Tau protein ; Thiopyridyl activation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary To study the influence of phosphorylation and oxidation on the repeat domains of human Tau protein, we faced the challenge to selectively dimerize two cysteine-containing peptides in the presence of a nearby phosphate group. To this end, we were able to demonstrate the utility of a selective dimerization approach by forming disulfide bonds in unprotected phosphopeptides and extended the methodology to unprotected glycopeptides. Activation of one cysteine of a peptide chain with 2,2′-dithiodipyridine and coupling this thiopyridyl-peptide to another peptide chain, containing an unprotected cysteine residue, yielded the mixed dimers in high purities and reasonable yields. Phosphate or sugar side chains on either peptide component remained unaffected during the activation and dimerization processes. While for mixed dimers the activated peptides were isolated by chromatography, homodimers were obtained by a simple one-pot reaction after 1 h. We demonstrate that cysteines can be dimerized in unprotected phosphopeptides and glycopeptides, without any side reactions affecting these posttranslational modifications.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00127968
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  • 2
    Electronic Resource
    Electronic Resource
    Cycloadditions, 53. New spirocyclic chiral dienes  -  synthesis and diastereoselective Diels-Alder reactions with N-phenylmaleimide (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 1455-1461 
    Details
    ISSN: 0947-3440
    Keywords: Dienes, chiral ; 1,3-Dioxin-4-ones ; (-)-Menthone ; Diels-Alder reactions, diastereoselective ; Cycloadditions, high-pressure ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis and diastereoselective Diels-Alder reactions of new spirocyclic chiral dienes are reported. Starting with diketene and (-)-menthone (1), we prepared the diastereomeric diketene-menthone adducts 2 and 3. Further derivatization and olefination afforded four chiral dienes 12-15. Diastereoselective Diels-Alder reactions of these dienes with N-phenylmaleimide (NPM) under high-pressure conditions yielded the corresponding cycloadducts 16-19. Olefination of 6-diethylphosphonomethyl-2,2-dimethyl-1,3-dioxin-4-one 8 with formaldehyde led to unexpected compounds 9-11 resulting from the originally formed olefination product.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199508198
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