Synthesis of pyrazine via chemoselective reduction of β-keto-α-oximino ester using baker’s yeast

Publication date: January 2016 Source:Journal of Molecular Catalysis B: Enzymatic, Volume 123 Author(s): Kilwoong Mo, Jin Hyeong Park, Soon Bang Kang, Youseung Kim, Yong Sup Lee, Jae Wook Lee, Gyochang Keum The synthesis of pyrazines by the baker’s yeast-mediated reaction of β-keto-α-oximino esters and amides is described. Baker’s yeast reduced oximes selectively over ketones of β-keto-α-oximino esters to give the corresponding β-keto-α-amino ester intermediates, which underwent spontaneous dimerization followed by air-induced aromatization to yield pyrazines. The chemoselective reduction of β-keto-α-oximino amides using baker’s yeast also afforded the corresponding pyrazines. Interestingly, both hydroximes and alkoximes gave the pyrazines by the baker’s yeast-mediated reduction via the corresponding amino ketones, the known precursors of pyrazines. The reaction was strongly dependent upon pH of reaction medium, and gave optimum yields at pH 5. These results demonstrate that pyrazines were synthesized efficiently and eco-friendly using a whole-cell biocatalytic system as an alternative to chemical reduction. Graphical abstract

Source: Journal of Molecular Catalysis B: Enzymatic - December 6, 2015 Category: Biochemistry Source Type: research