Bioconversion of 1,5-Anhydro-D-fructose to 1,5-Anhydro-D-glucitol and 1,5-Anhydro-D-mannitol Using Saccharomyces cerevisiae

High-temperature solvent-free synthesis of low-molecular-weight organogelators consisting of starch-derived 1,5-anhydro-d-glucitol coupled with fatty acids

“…Low-molecular-weight gelators form bers by self-assembly and conne the liquid between the bers, thereby eliminating the liquid's uidity and creating a gel. [1][2][3][4][5][6] We previously synthesized derivatives of 1,5-anhydro-D-glucitol (1,5-AG), a cyclic polyol obtained by enzymatic and fermentation treatments of starch, 7,8 containing various linear saturated fatty acids of different lengths via ester linkages, and reported that these compounds can gelatinize various organic solvents (C-AG series). [9][10][11] We also synthesized compounds in which a linear saturated fatty acid with an amide group was introduced into 1,5-AG via ester linkages to further strengthen the intermolecular hydrogen bond (GABA-AG series); as a result, the effect of the amide group produced a harder and more transparent gel than those of the C-AG series without an amide group.…”

Development of Low-Molecular-Mass Organogelators: Synthesis and Physical Properties of N-Linear Saturated Fatty Acyl-GABAs and Their Ester Derivatives

“…Due to these very weak intermolecular interactions, the C16AG gel was fragile to external physical force. 1,5-Anhydro- d -glucitol (1,5-AG) − was successfully derived from starch-derived 1,5-anhydro- d -fructose and had a structure in which the hydroxy group at the anomeric position of d -glucopyranose (Glc) is deoxygenated. Because there is no hydroxy group at the anomeric position, which is the most reactive position, it has excellent stability in acidic, alkaline, and high-temperature conditions.…”

Development of Novel Low-Molecular-Mass Oil-gelling Agents: Synthesis and Physical Properties of 1,5-Anhydro-D-glucitol and 1,5-Anhydro-D-mannitol Protected with Saturated Linear Fatty Acids

“…Recently, 1,5-anhydro-D-glucitol (1,5-AG) and 1,5-anhydro-D-mannitol (1,5-AM) were successfully synthesized from starch via 1,5-anhydro-D-fructose. 16) 17) 18) In 1,5-AG and 1,5-AM, the anomeric hydroxy groups of glucose and mannose, respectively, are deoxygenated. Since the anomeric hydroxy group is the most reactive hydroxy group among the hydroxy groups on glucose and mannose, 1,5-AG and 1,5-AM, which are deoxygenated here, are more stable than native glucose and mannose, respectively, under acidic, alkaline, and high-temperature conditions.…”