Selective conversion of glucosamine (G1cNH(2)) to deoxyfructosazine (DOF) and fructosatine (FZ) With additives was investigated. Significantly enhanced yield of DOF can be improved to 40.2% with B(OH)(3) as the additive. Chemical shift titration (via one-dimensional nuclear magnetic resonance (1D H-1 and C-13 NMR)) and two-dimensional nuclear magnetic resonance (2D NMR) including H-1-C-13 HSQC and H-1-H-1 COSY are used to investigate intermolecular interactions between B(OH)(3) and G1cNH(2). Diffusion-ordered NMR spectroscopy (DOSY) was further employed to identify intermediate species. Mechanistic investigation by NMR combined with electron spray ionization-mass spectroscopy (ESI-MS) discloses that a:mixed 1:1 boron complex was identified as the major species; shedding light on the promotional effects of B(OH)3, which is substantiated by density functional theory (DFT). Boron coordination effects make ring-opening and subsequent dehydration reaction thermodynamically and kinetically More favorable. Dehydration of dihydrofructosazine is a key step in controlling overall process (49.7 kcal/mol). Interestingly, chelating effect results in substantial reduction of this free-energy barrier (31.5 kcal/mol). Notably, FZ was gradually becoming the main product (yield up to 25.3%), with H2O2 as, the oxidant.