The electrochemical reduction of biotin (vitamin B7) and conversion into its ester

摘要: Abstract An electrochemical study on biotin (vitamin B7), performed in aprotic solvents and at a platinum electrode, revealed that approximately E f 0 = − 1.6 to 1.8 vs. (Fc/Fc+)/V ( formal reduction potential Fc ferrocene ) , is reduced by one-electron form its carboxylate anion dihydrogen via direct discharge of the carboxylic acid surface. The process appeared be chemically reversible time-frame cyclic voltammetry (CV) (t ≤ s), but not over extended period controlled electrolysis (CPE) (t ≥ min) where conversion into was found irreversible. A strategy functionalize biotin's carboxyl group established performing bulk reductive electrolysis, then reacting electrochemically generated with iodomethane afford methyl ester excellent yield (91%). Attenuated total reflectance–Fourier transform infrared (ATR–FTIR) spectroscopy successful identifying several distinct characteristic carbonyl absorbance peaks associated analogous forms available before after methylation.