Modified syntheses of dopamine-4-sulfate, epinephrine-3-sulfate, and norepinephrine-3-sulfate: determination of the position of the sulfate group by 1H-NMR spectroscopy
| Deutscher übersetzter Titel: | Modifizierte Synthesen von Dopamin-Sulfat, Adrenalin-3-Sulfat und Noradrenalin-3-Sulfat: Bestimmung der Stellung der Sulfatgruppe durch 1H-NMR-Spektroskopie |
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| Autor: | Lernhardt, U.; Strobel, G.; Schell, H.; Werle, E.; Weicker, H. |
| Erschienen in: | International journal of sports medicine |
| Veröffentlicht: | 9 (1988), Suppl. 2, S. S89-S92, Lit. |
| Format: | Literatur (SPOLIT) |
| Publikationstyp: | Zeitschriftenartikel |
| Medienart: | Gedruckte Ressource |
| Sprache: | Englisch |
| ISSN: | 0172-4622, 1439-3964 |
| Schlagworte: | |
| Online Zugang: | |
| Erfassungsnummer: | PU198807012420 |
| Quelle: | BISp |
Abstract
With respect to the growing interest in sulfoconjugated catecholamines (CAS), reliable syntheses of those substances including high purification and unequivocal identification are required. For the syntheses of the 3-O-sulfates of norepinephrine (NE) and epinephrine (EPI), modifications of the methods of Stolz and Arakawa et al. were performed. Noradrenalone and adrenalone were prepared according to the method of Stolz and sulfated by reaction with pyridine-sulfurtrioxide complex in dry pyridine at 60 deg C. After reduction of these ketosulfates by sodium borohydride in dry pyridine, NE-3-O-S and EPI-3-O-S were obtained respectively. We synthesized dopamine-4-O-sulfate (DA-4-O-S) by reaction of DA hydrochloride with pyridine-sulfurtrioxide complex in dry dimethylformamide at 20 deg C (Harbeson et al., 1983). The highly purified products (DA-4-O-S, EPI-3-O-S) were characterized by their melting points (mp), infrared spectra (IR), thin-layer chromatography (TLC), highperformance liquid chromatography (HPLC), elemental analysis, and 1H-nuclear magnetic resonance spectroscopy (1H-NMR). Verf.-Referat