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Digitale Medien

Selective dimerization of cysteines in glycopeptides and phosphopeptides (1997)

Hoffmann, Ralf ; Otvos, Laszlo

Springer

International journal of peptide research and therapeutics 3 (1997), S. 371-377

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ISSN: 1573-3904

Schlagwort(e): Alzheimer's disease ; Disulfide bond formation ; Peptide ; Repeat domains ; Tau protein ; Thiopyridyl activation

Quelle: Springer Online Journal Archives 1860-2000

Thema: Chemie und Pharmazie

Notizen: 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.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1007/BF00127968

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Digitale Medien

Cycloadditions, 53. New spirocyclic chiral dienes - synthesis and diastereoselective Diels-Alder reactions with N-phenylmaleimide (1995)

Hoffmann, Ralf ; Mattay, Jochen

Weinheim : Wiley-Blackwell

Liebigs Annalen 1995 (1995), S. 1455-1461

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ISSN: 0947-3440

Schlagwort(e): Dienes, chiral ; 1,3-Dioxin-4-ones ; (-)-Menthone ; Diels-Alder reactions, diastereoselective ; Cycloadditions, high-pressure ; Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: 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.

Zusätzliches Material: 1 Tab.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/jlac.1995199508198

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