Stability determination for cyclized 2,4-dinitrophenyl hydrazone derivative of glucose

Abstract Background The most well established tactic for the analysis of monosaccharaides, such as glucose, relies on derivatization procedures, using reagents as 2,4-dinitrophenylhydrazine (DNPH). Usually, the instability of the formed imine product deteriorates the detection of trace amounts of the sugar; rendering the spectrophotometric analysis of monosaccharaides extremely challenging. Methods In this study, we propose a modified derivatization procedure, reliant on the formation of a stable DNPH-glucose derivative, to aid in the spectrophotometric analysis of glucose. The derivatization procedure was customized to perform the product work-up step under acidic conditions. Results The proton rich media resulted in direct reduction of the Schiff’s base with concomitant intramolecular rearrangement of the product to yield a stable cyclized DNPH-glucose derivative. The annealed structure of the titled compound was verified by 1NMR, 13C-NMR, HMBC and X-ray crystallography. Conclusions The derivative revealed extended stability in spiked plasma samples which suggests a potential to employ the described procedure for glucose analysis and detection in biological samples