6-deoxy-6-bromoascorbic acid

6-deoxy-6-bromoascorbic acid is a **synthetic analog of ascorbic acid (vitamin C)**, characterized by the replacement of the hydroxyl group at the C-6 position with a bromine atom. This derivative is notable for its **selective substrate specificity for sodium-dependent vitamin C transporters (SVCT1 and SVCT2)**, but not for glucose transporters (GLUTs). Its unique interaction with SVCTs has enabled researchers to dissect vitamin C transport pathways in vivo[1][5]. Mechanistically, it is transported via SVCTs with kinetics similar to ascorbic acid but shows limited transport by GLUTs[5]. In laboratory studies, **6-deoxy-6-bromoascorbic acid exhibited antioxidant properties, inhibition of melanoma cell growth, and moderate antiscorbutic (anti-scurvy) activity** in animal models[1]. This compound is mainly a research tool for understanding vitamin C biology and potential anticancer research. Its preparation involves bromination of ascorbic acid[1], and the structural modification imparts improved stability in solution and enhanced transport pathway specificity.

Other names

6-bromoascorbate6-bromo-6-deoxy-(S)-ascorbic acid6-bromo-L-ascorbic acid6-deoxybromo ascorbateL-Ascorbic acid, 6-bromo-6-deoxy-(R)-5-((R)-2-Bromo-1-hydroxyethyl)-3,4-dihydroxyfuran-2(5H)-one