l-(1-13C)- and (2-13C)ascorbic acid: synthesis and NMR characterization

✍ Scribed by Kenneth N. Drew; Timothy J. Church; Bidisa Basu; Tapani Vuorinen; Anthony S. Serianni

• Publisher: Elsevier Science
• Year: 1996
• Tongue: English
• Weight: 456 KB
• Volume: 284
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(96)00008-0

✦ Synopsis

Apart from its well-known role in the prevention of scurvy, ascorbic acid (1, vitamin C) has been implicated in a number of diverse biological processes. For example, the monooxygenase, dopamine fl-hydroxylase, which catalyzes the hydroxylation of 3,4-dihydroxyphenylethylamine (dopamine) to noradrenaline (norepinephrine), requires 1 for activity. Several dioxygenases also require 1 as a substrate or cofactor. Thus, 1 is required in the hydroxylation of peptidyl-L-prolyl to peptidyl-trans-hydroxy-L-prolyl by the enzyme, prolyl hydroxylase, during collagen biosynthesis. More recently, it has been proposed that 1 may mediate inter-cellular (inter-organ) energy transfer in living systems [1] (Scheme 1).

In this process, the glycolytic pathway of an erythrocyte generates 1 from dehydroascorbate (2) through the participation of NADH (generated via the reaction catalyzed by D-glyceraldehyde 3-phosphate dehydrogenase), and exports it. Compound 1 is subse-* Corresponding author.