Lipase‐Catalyzed Synthesis of d‐Psicose Fatty Acid Diesters and their Emulsification Activities

Abstract

The diesterification of D-psicose (the C-3 epimer of D-fructose) with fatty acid vinyl esters of selected acyl chain lengths (C 8 , C 10 , and C 12 ) was successfully carried out using Candida antarctica lipase (Novozym 435) at 45°C for 24 h to give the 1,6-diacyl-D-psicofuranoses with a high regioselectivity in good yields (83-90%). These diesters of D-psicose have hydrophilic-lipophilic balance (HLB) values (6.5-8.2) similar to HLB values of monoglyceride compounds which constitute the largest single type of emulsifiers employed by the food industry. Ability of the D-psicose diesters to stabilize oil-in-water emulsions and the weight-averaged oil-droplet diameter in the emulsions was evaluated in this study. Emulsion stability of oil droplets stabilized by D-psicose dicaprylate (0.3%, w/v in oil phase) was comparable to D-fructose dicaprylate (0.2%, w/v). It was further confirmed that the D-psicose diesters exhibited an emulsification activity depending on the chain length of fatty acid; D-psicose dicaprate showed better emulsion stability than the other diesters.

Biocatalytic Synthesis of D-Allulose Using Novel D-Tagatose 3-Epimerase From Christensenella minuta

“…D -allulose is a C-3 epimer of D -fructose having 70% sweetness and 0.3% energy relative to sucrose (Matsuo et al, 2001 ). Some of the notable physiological properties of D -allulose are: (1) anti-hyperglycemic effects (Hossain et al, 2011 , 2015 ), (2) anti-hyperlipidemic effects (Matsuo et al, 2001 ; Afach et al, 2008 ), (3) anti-inflammatory effects (Oh, 2007 ), (4) neuroprotective effects (Takata et al, 2005 ), (5) reactive oxygen species (ROS) scavenging activity scavenging activity (Suna et al, 2007 ). Besides its therapeutic potential, D -allulose is also used as food flavor and processing since it reduces the oxidation process greatly (Sun et al, 2004 ).…”

Biochemical characterization of a d‐psicose 3‐epimerase from Treponema primitiaZAS‐1 and its application on enzymatic production of d‐psicose

“…It also improves the gelling properties of foods through the Maillard reaction . Meanwhile, d ‐psicose has advantageous physiological functions, including the ability to reduce fat accumulation, reactive oxygen species scavenging activity, neuroprotection, low glycemic response, insulin resistance and the ability to reduce blood lipid levels . Recently, d ‐psicose was declared ‘generally regarded as safe’ (GRAS) for food production by the Food and Drug Administration (FDA).…”

“…5,6 Meanwhile, D-psicose has advantageous physiological functions, including the ability to reduce fat accumulation, 7 reactive oxygen species scavenging activity, 8 neuroprotection, 9 low glycemic response, 10 -12 insulin resistance 11,13 and the ability to reduce blood lipid levels. 7,14 Recently, D-psicose was declared 'generally regarded as safe' (GRAS) for food production by the Food and Drug Administration (FDA). Hence D-psicose is a feasible substitute for sucrose 15 and represents a new type of sweetener with a bright commercial future for the food industry.…”

Optimization of the Solvent‐Free Lipase‐Catalyzed Synthesis of Fructose‐Oleic Acid Ester Through Programming of Water Removal

“…The major problem is the poor miscibility of polar and non-polar substrates, resulting in slow reaction rates. Although several methods have been successfully utilized to enhance the miscibility, particularly the employment of co-solvents: polar organic solvents [9][10][11] supercritical CO 2 [12,13] and ionic liquids [14,15], their use involves several disadvantages, including the high cost of solvents and/or their recovery or disposal, reduction of process safety, and the environmental impact of solvent utilization.…”