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Int J Sports Med 1988; 09: 89-92
DOI: 10.1055/s-2008-1025622
© Georg Thieme Verlag Stuttgart · New York

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

U. Lernhardt, G. Strobel, H. Schell, E. Werle, H. Weicker
  • Department of Pathophysiology and Sports Medicine, Medical Clinic and Policlinic, University of Heidelberg, FRG
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Publication Date:
14 March 2008 (online)

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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 (12) and Arakawa et al. (1) were performed. Noradrenalone and adrenal-one were prepared according to the method of Stolz (12) and sulfated by reaction with pyridine-sulfurtrioxide complex in dry pyridine at 60°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°C (Harbeson et al., 1983). The highly purified products (DA-4-O-S, NE-3-O-S, EPI-3-O-S) were characterized by their melting points (mp), infrared spectra (IR), thin-layer chromatography (TLC), high-performance liquid chromatography (HPLC), elemental analysis, and 1H-nuclear magnetic resonance spectroscopy (1H-NMR).

Key words

catecholamines - sulfoconjugation - 1H-nuclear magnetic resonance spectroscopy