7231-46-1Relevant academic research and scientific papers
Efficient Bioconversion of Sucrose to High-Value-Added Glucaric Acid by In Vitro Metabolic Engineering
Su, Hui-Hui,Guo, Ze-Wang,Wu, Xiao-Ling,Xu, Pei,Li, Ning,Zong, Min-Hua,Lou, Wen-Yong
, p. 2278 - 2285 (2019)
Glucaric acid (GA) is a major value-added chemicals feedstock and additive, especially in the food, cosmetics, and pharmaceutical industries. The increasing demand for GA is driving the search for a more efficient and less costly production pathway. In this study, a new in vitro multi-enzyme cascade system was developed, which converts sucrose efficiently to GA in a single vessel. The in vitro system, which does not require adenosine triphosphate (ATP) or nicotinamide adenine dinucleotide (NAD+) supplementation, contains seven enzymes. All enzymes were chosen from the BRENDA and NCBI databases and were expressed efficiently in Escherichia coli BL21(DE3). All seven enzymes were combined in an in vitro cascade system, and the reaction conditions were optimized. Under the optimized conditions, the in vitro seven-enzyme cascade system converted 50 mm sucrose to 34.8 mm GA with high efficiency (75 % of the theoretical yield). This system represents an alternative pathway for more efficient and less costly production of GA, which could be adapted for the synthesis of other value-added chemicals.
Conformation analysis of d-glucaric acid in deuterium oxide by NMR based on its JHH and JCH coupling constants
Enomoto-Rogers, Yukiko,Iwata, Tadahisa,Masaki, Hisaharu,Ito, Tetsuya,Furihata, Kazuo
, p. 561 - 567 (2016)
d-Glucaric acid (GA) is an aldaric acid and consists of an asymmetric acyclic sugar backbone with a carboxyl group positioned at either end of its structure (i.e., the C1 and C6 positions). The purpose of this study was to conduct a conformation analysis of flexible GA as a solution in deuterium oxide by NMR spectroscopy, based on J-resolved conformation analysis using protonproton (3JHH) and protoncarbon (2JCH and 3JCH) coupling constants, as well as nuclear overhauser effect spectroscopy (NOESY). The 2JCH and 3JCH coupling constants were measured using the J-resolved heteronuclear multiple bond correlation (HMBC) NMR technique. NOESY correlation experiments indicated that H2 and H5 were in close proximity, despite the fact that these protons were separated by too large distance in the fully extended form of the chain structure to provide a NOESY correlation. The validities of the three possible conformers along the three different bonds (i.e., C2C3, C3C4, and C4C5) were evaluated sequentially based on the J-coupling values and the NOESY correlations. The results of these analyses suggested that there were three dominant conformers of GA, including conformer 1, which was H2H3:gauche, H3H4:anti, and H4H5:gauche; conformer 2, which was H2H3:gauche, H3H4:anti, and H4H5:anti; and conformer 3, which was H2H3:gauche, H3H4: gauche, and H4H5:anti. These results also suggested that all three of these conformers exist in equilibrium with each other. Lastly, the results of the current study suggested that the conformational structures of GA in solution were bent rather than being fully extended. Copyright
BIOSYNTHESIS OF D-GLUCARIC ACID IN MAMMALS: A FREE-RADICAL MECHANISM?
Marsh, Charles A.
, p. 119 - 131 (1986)
In the presence of iron salts and hydrogen peroxide, D-glucuronic acid was converted into D-glucaric acid.The reaction was strongly inhibited by free-radical scavengers and is ascribed to the action of the hydroxyl radical.The formation of D-glucarate was dependent upon pH and occurred in the presence of some iron-complexing agents.The first product of oxidation was a lactone that was a strong inhibitor of β-D-glucuronidase and assumed to be D-glucaro-1,5-lactone.Microsomal preparations in the presence of NADPH also produced D-glucarate from D-glucuronic acid, presumably due to formation of hydrogen peroxide, and the product was an inhibitor of β-D-glucuronidase.Superoxide did not produce D-glucarate from D-glucuronate.The cytochrome P450 system is more likely than "glucuronolactone dehydrogenase" to be responsible for the production of D-glucaric acid in vivo.
Boosting electrocatalytic nitrogen fixation: Via energy-efficient anodic oxidation of sodium gluconate
Zhao, Lu,Kuang, Xuan,Chen, Cheng,Sun, Xu,Wang, Zhiling,Wei, Qin
, p. 10170 - 10173 (2019)
Here, we report an anodic replacement of the water oxidation reaction with more readily oxidizable species to facilitate ambient electrocatalytic nitrogen reduction reaction (NRR). A self-supported catalyst, CuII-MOF on carbon cloth (JUC-1000/CC), acts as a versatile cathode and anode for both NRR and electro-oxidation of sodium gluconate to glucaric acid. Impressively, the two-electrode system requires a potential of only 0.4 V to achieve an NH3 yield rate of 24.7 μg h-1 mgcat-1, an FE of 11.90% and an SA selectivity of 96.96%, and shows strong electrochemical stability. This study reveals that the strategy avoids the sacrifice of the NH3 yield to increase FE, and offers an efficient and simultaneous electrosynthesis of NH3 and SA.
Catalytic wet air oxidation of D-glucose by perovskite type oxides (Fe, Co, Mn) for the synthesis of value-added chemicals
Geobaldo, Francesco,Pirone, Raffaele,Russo, Nunzio,Scelfo, Simone
, (2022/03/15)
The conversion of common biomasses derived, as D-glucose, into value-added chemicals has received highest attention in the last few years. Among all processes, the catalytic wet air oxidation (CWAO) of derived biomasses using noble metal-based heterogeneo
PROCESSES FOR PREPARING ALDARIC, ALDONIC, AND URONIC ACIDS
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Paragraph 0087-0091; 00100-00102, (2021/05/29)
Various processes for preparing aldaric acids, aldonic acids, uronic acids, and/or lactone(s) thereof are described. For example, processes for preparing a C2-C7 aldaric acid and/or lactone(s) thereof by the catalytic oxidation of a C2-C7 aldonic acid and/or lactone(s) thereof and/or a C2-C7 aldose are described.
Efficient Catalysts for the Green Synthesis of Adipic Acid from Biomass
Deng, Weiping,Yan, Longfei,Wang, Binju,Zhang, Qihui,Song, Haiyan,Wang, Shanshan,Zhang, Qinghong,Wang, Ye
supporting information, p. 4712 - 4719 (2021/01/20)
Green synthesis of adipic acid from renewable biomass is a very attractive goal of sustainable chemistry. Herein, we report efficient catalysts for a two-step transformation of cellulose-derived glucose into adipic acid via glucaric acid. Carbon nanotube-supported platinum nanoparticles are found to work efficiently for the oxidation of glucose to glucaric acid. An activated carbon-supported bifunctional catalyst composed of rhenium oxide and palladium is discovered to be powerful for the removal of four hydroxyl groups in glucaric acid, affording adipic acid with a 99 % yield. Rhenium oxide functions for the deoxygenation but is less efficient for four hydroxyl group removal. The co-presence of palladium not only catalyzes the hydrogenation of olefin intermediates but also synergistically facilitates the deoxygenation. This work presents a green route for adipic acid synthesis and offers a bifunctional-catalysis strategy for efficient deoxygenation.
PROCESSES FOR PREPARING ALDARIC, ALDONIC, AND URONIC ACIDS
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Paragraph 0132-0143, (2021/05/29)
Various processes for preparing aldaric acids, aldonic acids, uronic acids, and/or lactone(s) thereof are described. For example, processes for preparing a C5-C6 aldaric acid and/or lactone(s) thereof by the catalytic oxidation of a C5-C6 aldonic acid and/or lactone(s) thereof and/or a C5-C6 aldose are described.
Bimetallic AuPt/TiO2Catalysts for Direct Oxidation of Glucose and Gluconic Acid to Tartaric Acid in the Presence of Molecular O2
Ding, Jie,Jin, Xin,Lai, Linyi,Liu, Mengyuan,Sun, Yu,Wang, Jinyao,Xia, Qi,Yan, Hao,Yang, Chaohe,Zhang, Guangyu,Zhang, Wenxiang
, p. 10932 - 10945 (2020/11/23)
Tartaric acid is an important industrial building block in the food and polymer industry. However, green manufacture of tartaric acid remains a grand challenge in this area. To date, chemical synthesis from nitric acid-facilitated glucose oxidation leads to only a one-pot aqueous-phase oxidation of glucose and gluconic acid using bimetallic AuPt/TiO2 catalysts in the presence of molecular O2, with ～50% yield toward tartaric acid at 110 °C and 2 MPa. Structural characterization and density functional theory (DFT) calculation reveal that the lattice mismatch between fcc Pt and bcc Au induces the formation of twinned boundaries in nanoclusters and Jahn-Teller distortion in an electronic field. Such structural and electronic reconfiguration leads to enhanced σ-activation of the C-H bond competing with π-πelectronic sharing of the C═O bond on the catalyst surface. As a result, both C-H (oxidation) and C-C (decarboxylation) bond cleavage reactions synergistically occur on the surface of bimetallic AuPt/TiO2 catalysts. Therefore, glucose and gluconic acid can be efficiently transformed into tartaric acid in a base-free medium. Lattice distortion-enhanced reconfiguration of the electronic field in Pt-based bimetallic nanocatalysts can be utilized in many other energy and environmental fields for catalyzing synergistic oxidation reactions.
Visible-light-driven selective oxidation of glucose in water with H-ZSM-5 zeolite supported biomimetic photocatalyst
Chen, Rui,Yang, Changjun,Zhang, Quanquan,Zhang, Bingguang,Deng, Kejian
, p. 297 - 305 (2019/05/24)
A new iron tetra(2,3-bis(butylthio)maleonitrile)porphyrazine (FePz(SBu)8)has been synthesized, then it was loaded on H-ZSM-5 zeolite to obtain a supported biomimetic photocatalyst H-ZSM-5/FePz(SBu)8. Using H2O2 as oxidant, the photocatalytic selective oxidation of glucose in water under visible light (λ ≥ 420 nm)irradiation was carried out in presence of H-ZSM-5/FePz(SBu)8. Under such conditions, the glucose can be efficiently converted into value-added chemicals such as glucaric acid, gluconic acid, arabinose, glycerol and formic acid. More importantly, in comparison with pure FePz(SBu)8 and pure H-ZSM-5 zeolite, the H-ZSM-5/FePz(SBu)8 exhibited a higher photocatalytic activity for glucose oxidation and the formation of glucaric acid was observed only when H-ZSM-5/FePz(SBu)8 was used, deriving from the synergistic effect between FePz(SBu)8 and H-ZSM-5 zeolite. Some reaction parameters of glucose oxidation catalyzed by the H-ZSM-5/FePz(SBu)8 were discussed, such as loading amount of FePz(SBu)8, H2O2:glucose ratio, glucose concentration, and so on. It was demonstrated that the Soret-band of FePz(SBu)8 contributed more to the visible light photocatalytic activity than the Q-band during the photocatalytic process. The stability of H-ZSM-5/FePz(SBu)8 during the photocatalytic process was further evaluated by the reusability test. In addition, the generation of reactive oxygen species was determined by electron spin resonance (ESR)technology and scavenger experiments. A possible reaction pathway of glucose oxidation was also discussed.
