Improved Synthesis of 5-Nitrohomovanillic Acid and 6-Nitrohomovanillic Acid as Probes for Metabolism Studies of Endothelium-Derived Dopamines: Identification in Human Amniotic Fluid.
Rosa Sparaco, Pierfrancesco Cinque, Antonia Scognamiglio, Stefania Vertuccio, Giuseppe Caliendo, Ferdinando Fiorino, Angela Corvino, Elisa Magli, Elisa Perissutti, Vincenzo Santagada, Beatrice Severino, Giorgia Andreozzi, Paolo Luciano, Carmela Dell'Aversano, Alex Henrique Miller
Abstract
Open Access6-Nitrodopamine is an endogenous catecholamine responsible for numerous biological activities. Here, an improved method for the synthesis of both 6-nitrohomovanillic acid (6-NHVA) and its regioisomer 5-nitrohomovanillic acid (5-NHVA) is reported. The developed one-step synthetic procedures ensured the efficient preparation of the target compounds in good yields. Comprehensive structural characterization was achieved through one- and two-dimensional NMR studies and by high-resolution mass spectrometry (HR-MS/MS). The presence of both substances was identified in human amniotic fluid by LC-MS/MS.