Synthesis of 2-Deoxy-L-ascorbic Acid

摘要

Ascorbic acid (vitamin C) functions as an electron donor and antioxidant for several enzymes and is implicated in host defense mechanisms, endocrine function, and other biological processes. Recent research on the biochemistry of ascorbic acid has been focused on the mechanisms of action of the vitamin as well as on concentrations required for its optimal function. For example, recent clinical studies have shown that the recommended dietary allowance (RDA) for ascorbic acid may be too low. Recent kinetic measurements of transport inhibition by 6-deoxy-6-haloascorbic acid analogues established the presence of separate pathways for the translocation of ascorbic acid and dehydroascorbic acid, suggesting also that the 6-OH group of ascorbic acid is not critical for transport and, presumably, for other functions. In order to extend these studies to an investigation of the importance of the 2-hydroxyl group for ascorbic acid transport, we have prepared 2-deoxy-L-ascorbic acid 1. Compound 1 could also be a versatile intermediate for the preparation of other 2-deoxyascorbic acids, e.g., their as yet unreported 2-halo or 2-alkyl derivatives.