6-Deoxy-6-fluoro-l-ascorbic acid: crystal structure and oxidative degradation

Radiosynthesis and preliminary biodistribution in mice of 6‐deoxy‐6‐[131I]iodo‐L‐ascorbic acid

“…HPLC purification using a reversephase column gave 6-deoxy-6-[ 131 I]iodo-L-ascorbic acid in radiochemical yield of 36-60% with high radiochemical purity and satisfactory-specific radioactivity in a total preparation time of 90 min. Biodistribution studies in fibrosarcoma-bearing mice showed a high uptake in the adrenal glands, accompanied by low activity of tumor accumulation, accumulation properties similar to previous results obtained with 14 C-labeled ascorbic acid and 6-deoxy-6-[ 18 F]fluoro-L-ascorbic acid, in spite of high level of deiodination. …”

“…Thus, it is most likely that the activities of these specific membrane transporters crucially influence transport, intracellular accumulation, and recycling of AsA in the living body. 4 Studies of tissue distribution of the radioactivity of 14 C-labeled AsA in animals were initially carried out mainly using wholebody autoradiography, and high levels of radioactivity were observed in the adrenal glands, pituitary glands and parotid glands, depending on the time after injection. [5][6][7] Colombetti et al proposed that AsA might be useful as a potential imaging agent of the pituitary gland if labeled with a suitable radionuclide.…”

Thioltranferase Mediated Ascorbate Recycling in Human Lens Epithelial Cells

“…It has been well documented that the DHA is very unstable, and, if it is not reduced to ascorbate, it can be irreversibly oxidized to L-erythrulose and L-threose, although existence of the latter sugar is controversial. 28 It has also been shown that DHA is irreversibly converted to 2,3-DKG, both chemically and enzymatically in vivo. 36,37 These ascorbate degradation products can undergo a Maillard reaction with proteins, which are responsible for browning and cross-linking of proteins in certain diseases and in aging and also can contribute to cataract formation.…”

“…6-Fluoro-6-deoxy ascorbic acid (F-ASA) was synthesized in the laboratory of Vincent Monnier at the Case Western Reserve University, as previously described. 28 All the other chemicals and reagents were standard commercial products of analytical grade.…”

“…Fluoroascorbic acid (6-deoxy-6-fluoro-ascorbic acid) was synthesized as previously described. 28 For the production of fluoro-DHA (F-DHA), fluoroascorbic acid (F-ASA) was dissolved in ice-cold water (Mili Q; Millipore, Bedford, MA) and 10 L bromine (catalog no. B8548, minimum 99.5%, Sigma-Aldrich) was added.…”