Mechanism of formation of 5-(hydroxymethyl)-2-furaldehyde from d-fructose and sucrose

When a proton attacks cellobiose in the gas phase: ab initio molecular dynamics simulations

“…Qian et al [12][13][14] were first to study protonated sugar monomers of glucose and xylose, by AIMD and recently by metadynamics. 15 The authors confirm a previously proposed hydrolysis mechanism for xylose 16,17 and propose several degradation pathways for glucose, involving water extraction. 15 Acidic dehydration and competing reaction pathways were studied computationally in b-glucose, and free energies for such reactions were characterized recently in great detail.…”

Bifunctional Solid Catalysts for the Selective Conversion of Fructose to 5-Hydroxymethylfurfural

“…Similar selectivities have been reported for solid acid catalysts such as PK-216, Amberlyst 15, H-Mordenite, and Nafion NR50 [9,18]. Higher selectivity can be achieved by addition of dimethylsulfoxide (DMSO) or dimethylformamide (DMF) as promoters [17,19,20], however, product isolation is complicated by their high boiling points [21].…”

Renal organic anion transporters OAT1 and OAT3 mediate the cellular accumulation of 5-sulfooxymethylfurfural, a reactive, nephrotoxic metabolite of the Maillard product 5-hydroxymethylfurfural

“…It is formed when reducing hexose moieties are heated in the presence of amino acids or proteins (Maillard reaction) [1] and via direct thermal dehydration of fructose, sucrose and glucose [2]. HMF is present at high levels in many foods, with particularly high concentrations found in caramel products (up to 9.5 g/kg), dried fruit (especially plums), old…”