Oxidative Nebenreaktionen bei der Dansylierung von SH-Verbindungen
- 1 January 1976
- journal article
- research article
- Published by Walter de Gruyter GmbH in Hoppe-Seyler´s Zeitschrift Für Physiologische Chemie
- Vol. 357 (1), 225-232
- https://doi.org/10.1515/bchm2.1976.357.1.225
Abstract
Dansyl chloride can act as an oxidizing agent on compounds which are easily oxidized. During the reaction of mercaptanes, e.g. cysteine, homocysteine, cysteamine, with dansyl chloride, the corresponding disulfides are formed and dansyl chloride is reduced to 5-dimethylaminonaphthalene 1-sulfinic acid. This reaction is so rapid that the normal dansylation can take place only after complete oxidation of all SH-compounds. Therefore only the dansyl derivatives of the corresponding disulfides are formed during normal dansylation of SH-compounds. If different SH-compounds are present in the reaction mixture mixed disulfides are formed as well. These can be separated by microchromatography on 3 .times. 3 cm micropolyamide sheets. Dependent on the concentration of dansyl chloride, 6 or even 15 different dansylated disulfides are formed from 3 different SH-compounds so that interpretation of these chromatograms is difficult. The actual dansylmercaptanes (e.g., dansylcysteine, dansylhomocysteine, dansylcysteamine) can be prepared by reduction of the dansylated disulfides with suitable reducing agents.This publication has 10 references indexed in Scilit:
- Thin-layer chromatography of 1-dimethylaminonaphthalene-5-sulphonyl derivatives of amino acids present in superfusates of cat cerebral cortexBiochemical Journal, 1967
- Zur chromatographie einiger i-Dimethylamino-naphthalin-5- sulfonyl-derivate auf kieselgel g-schichtenJournal of Chromatography A, 1967
- Quantitative Bestimmung von Aminen und von Aminosäuren als 1-Dimethylamino-naphthalin-5-sulfonsÄureamide auf DünnschichtchromatogrammenAnalytical and Bioanalytical Chemistry, 1966
- The separation of 1-dimethylaminonaphthalene-5-sulphonamido acids (DNS-amino acids) by thin-layer chromatographyJournal of Chromatography A, 1965
- A Nuclear Magnetic Resonance Study of the Structures of L- and meso-Cystine in Aqueous Solutions1Journal of the American Chemical Society, 1965
- Dithiothreitol, a New Protective Reagent for SH Groups*Biochemistry, 1964
- The active centre of chymotrypsinBiochimica et Biophysica Acta, 1956
- CCXLI.—Syntheses of disulphoxidesJournal of the Chemical Society, Transactions, 1925
- Verhalten der Chloranhydride organischer Sulfonsäuren gegen Thiophenole und Thioalkohole bei Gegenwart von AlkaliEuropean Journal of Inorganic Chemistry, 1891
- Versuche zur Darstellung von Thioäthern der Benzolsulfonsäure und ParatoluolsulfonsäureEuropean Journal of Inorganic Chemistry, 1876