Vinylogy the α-carbon immediately adjacent to the carbonyl, as would a simple enolate. Allylic electrophiles often react by vinylogous attack of a nucleophile rather than direct addition. A further example of vinylogous reactivity: ascorbic acid (Vitamin C) behaves as a vinylogous carboxylic acid by involvement of its carbonyl moiety, a vinyl group within the ring, and the lone pair on the hydroxyl group acting as the conjugated system. Acidity of the hydroxyl proton at the terminus of the vinyl group in ascorbic acid is more comparable to a typical carboxylic acid than an alcohol because two major resonance structures stabilize the
Chemistry of ascorbic acid acid. American and Chinese researchers are competing to engineer a mutant that can carry out a one-pot fermentation directly from glucose to 2-KGA, bypassing both the need for a second fermentation and the need to reduce glucose to sorbitol. There exists a -ascorbic acid, which does not occur in nature but can be synthesized artificially. To be specific, -ascorbate is known to participate in many specific enzyme reactions that require the correct enantiomer (-ascorbate and not -ascorbate). -Ascorbic acid has a specific rotation of [α] = +23°. The traditional way to analyze the ascorbic acid content is the process of