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D-Erythrose is an aldose with four carbon atoms, chemical formula C4H8O4, CAS 583-50-6, molecular weight 120.10 g/mol. It exists as a white crystalline solid. Its appearance may vary depending on method of preparation and purity. It has good solubility in water. It can form hydrogen bonds with water and interact with water molecules. In addition, D-(-)-ERYTHROSE is also soluble in some organic solvents, such as ethanol and methanol. It is an optical isomer with optical properties. Its optical rotation is negative and is usually prefixed with D-(-)- to indicate its optical activity. This means that it rotates the light passing through it to the left by a specific angle. Crystal structures are polymorphic and can adopt different lattice forms. Based on its chemical structure and general properties of organic compounds, we can infer that it has a certain flammability. Widely used in biological research.
It can be used as a substrate for enzyme activity determination and metabolic pathway research. By tracing its metabolic pathways in cells, it is possible to gain insight into the mechanisms of cellular energy metabolism and carbohydrate metabolism. As a natural sugar substance, it is widely used in the cosmetic industry. It has moisturizing, antioxidant and anti-inflammatory properties, and is used as an ingredient in skin care, facial masks and hair care products. It increases skin hydration and improves skin smoothness for more youthful and healthy looking skin. It has important uses in biological research, drug synthesis, cosmetic industry and food industry. Its diverse fields of application demonstrate the importance and potential of this compound.
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Chemical Formula |
C4H8O4 |
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Exact Mass |
120 |
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Molecular Weight |
120 |
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m/z |
120 (100.0%), 121 (4.3%) |
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Elemental Analysis |
C, 40.00; H, 6.71; O, 53.28 |
D-Erythrose, as a multifunctional biobased platform compound, has penetrated into multiple strategic fields such as medicine, materials, and agriculture. With the continuous breakthroughs in synthetic biology and metabolic engineering, the industrial value of this compound will be deeply explored.
Core roles in biochemistry and metabolism research
As a four carbon aldose, it participates in multiple core metabolic pathways in organisms. Its most significant role is as a key intermediate in the pentose phosphate pathway (PPP), which not only generates NADPH (reduced coenzyme II) and ribose-5-phosphate, but also converts D - (-) - erythritol to D-erythrise-4-phosphate through oxidative branching, ultimately producing pyruvic acid or entering the gluconeogenesis pathway. Research has shown that PPP is abnormally active in tumor cells, and the metabolic flux of D - (-) - erythritol can become a potential target for cancer treatment. For example, blocking PPP by inhibiting the activity of transketolase (TKT) can significantly enhance the killing effect of chemotherapy drugs on pancreatic cancer cells.
In microbial metabolic engineering, it is used to construct non natural metabolic pathways. After genetic modification, Escherichia coli can be transformed into 1,3-propanediol precursor, providing a new pathway for the production of biobased materials. In addition, this compound plays a signaling molecule role in plant stress resistance mechanisms, and exogenous application of this substance can activate the antioxidant enzyme system in Arabidopsis thaliana, enhancing salt stress tolerance.
Strategic value in chiral drug synthesis
Its chiral center (C2) makes it an important chiral source for asymmetric synthesis. Multiple high-value chiral intermediates can be prepared through region selective oxidation and reduction reactions
Key intermediate of anti HIV drugs: (S) - glycidyl ester can be synthesized through Sharpless asymmetric epoxidation reaction, which is used to prepare the side chain of integrase inhibitor Raltegravir.
β - lactam antibiotic precursor: Through enzyme catalyzed reverse aldol condensation reaction, (3S) -3-hydroxybutyric acid methyl ester is generated, which is used for constructing carbapenem antibiotic parent nuclei.
Synthesis of neuroprotective agents: After reacting with propargyl bromide, (R) -3-butyn-2-ol is obtained through Lindlar catalyzed hydrogenation, which is used to prepare the key fragment of Rasagiline, a Parkinson's disease treatment drug.
In industry, it has been used as a chiral intermediate for the kilogram level production of the antiepileptic drug Levetiracetam, achieving a 98% ee value through asymmetric Henry reaction.
Development of functional foods and nutritional fortifiers
Although its sweetness is only 60% of sucrose, its unique metabolic characteristics make it highly sought after in the field of functional foods
Zero calorie sweetener combination: When combined with erythritol and steviol glycosides, it can achieve a synergistic sweetener effect while masking the bitterness afterwards. Japan has approved it as an additive for "specific health food".
Sports nutrition supplement: As a PPP metabolic enhancer, it can enhance the NADPH reserve of muscle cells and strengthen antioxidant defense ability. Clinical trials have shown that supplementing with this substance can prolong athletes' exhaustion time by 17.3%.
Intestinal microbiota regulator: In vitro fermentation experiments have shown that it can promote the proliferation of bifidobacteria and lactobacilli, inhibit the growth of harmful bacteria in the Enterobacteriaceae family, and is expected to be used in the development of prebiotic products.
In infant formula, as a precursor for ribose synthesis, it has a supportive effect on nucleotide metabolism and has been included in the list of new food ingredients by the European Union.
Innovative application of bio based material precursors
Its molecular structure endows it with the potential to become a biobased chemical platform:
Degradable polyester monomer: Succinic acid is generated through oxidative fracture, and then polymerized to obtain PBS (polybutylene succinate), which has better mechanical properties than traditional petroleum based polyesters.
Chiral ligand synthesis: C2 symmetric bidentate ligands prepared by reacting with amino alcohols exhibit excellent enantioselectivity (ee>99%) in asymmetric catalytic hydrogenation reactions.
Biobased solvent development: Tetrahydroerythritol prepared by catalytic hydrogenation, with a boiling point of 218 ℃, can be used as a green solvent to replace traditional chlorinated hydrocarbons.
In the field of biofuels, yeast strains modified through metabolic engineering can convert D - (-) - erythritol into isobutanol, with a theoretical conversion efficiency of 0.46 g/g, which is higher than the traditional bio butanol production route.
Clinical diagnosis and drug delivery system
The application in the pharmaceutical field is expanding to diagnostic reagents and drug carriers:
Tumor contrast agent: Its derivatives can be selectively taken up by tumor cells active in the pentose phosphate pathway and used for PET-CT imaging. Pre clinical studies showed that the tumor/background ratio of 68Ga labeled erythrin derivatives in breast cancer models reached 5.2:1.
Targeted drug carrier: By connecting doxorubicin to erythritol modified liposomes through click chemistry, PPP metabolism dependent tumor targeted delivery can be achieved. Animal experiments have shown that drug accumulation at the tumor site is increased by 3.1 times.
Metabolic disease markers: the level of D - (-) - erythrin in plasma is negatively correlated with insulin resistance index, which may be a biomarker for early screening of type 2 diabetes.
Agriculture and Environmental Sustainable Development
In the field of agriculture, it demonstrates multiple application values:
Stress inducer: Foliar spraying can activate the antioxidant system of crops, and field trials of wheat have shown a 22% increase in yield retention under drought stress.
Biological pesticide synergist: In combination with Bt toxin formulations, it can enhance the sensitivity of insect midgut cells to toxins and improve control effectiveness by 40%.
Soil amendments: promote the optimization of rhizosphere microbial community structure, increase the abundance of nitrogen fixing bacteria, and improve nitrogen fixation efficiency by 18% in soybean continuous cropping obstacle fields.
In terms of environmental remediation, as a co metabolic substrate, it can enhance the degradation ability of microorganisms towards polychlorinated biphenyls, and has potential applications in bioremediation of polluted soil.
The preparation method of D erythrose , concrete steps are as follows:
1) configuration structure stabilizer solution; said structure stabilizer can be borax, can also be boric acid, other boron-containing compounds that can generate B(OH)4- in water and acetone etc. can be combined with two hydroxyl groups on glucose Substances that form five-membered rings or six-membered rings; the concentration of the structure stabilizer is 0.1-2.5 mol/liter, and the pH is 7-14.
2) Dissolving sugars in the above solution; the sugars can be five-carbon sugars, six-carbon sugars, disaccharides or other polysaccharides; the sugar concentration is 1wt%~50wt%.
3) Selectively add a basic catalyst in the above system; in the basic catalyst, the homogeneous basic catalyst can be phosphate, hydrogen phosphate, sodium hydroxide or other substances that can make the pH of the solution between 9-14 Alkaline substance, solid-phase alkaline catalyst can be hydrotalcite etc.
4) Place the above reaction solution in an oil bath, oven or microwave reactor for reaction at a temperature of 100-180°C; reaction time: 1 minute to 3 hours for microwave radiation, and 1-12 hours for heating in an oil bath or oven.
5) Separating the above reaction solution through a high-performance liquid chromatography preparative column to obtain D-erythrose. The separation conditions of the high performance liquid chromatography preparative column are: the column temperature is 38-45° C., and the concentration of the mobile phase is 0.4-0.6 millimolar dilute sulfuric acid. Preferably, the column temperature is 40°C, and the concentration of the mobile phase is 0.5 millimolar dilute sulfuric acid.
The method for preparing D erythrose by the above method is applicable to various sugar sources, and the solution can be in a large amount with a wide concentration range. The whole process is carried out in one step, and the process is simple. The reaction catalyst has a wide range of choices, and the common alkaline solution for homogeneous catalysis can be used. The requirement for alkalinity is relatively mild, so the corrosion to equipment is relatively small. The distribution of product composition is very narrow, and there are basically no other by-products. The yield of the method is very high, reaching more than 78.5% (10wt% glucose) and 46.9% (10wt% fructose). Even starting from the five-carbon sugar xylose, the yield of D erythrose is 35.8%.
Method 2:
A new method for producing D-Erythrose from gluconic acid or its salts using a chemical route. An aqueous solution of gluconate is contacted with hydrogen peroxide in the presence of a salt of a metal selected from cobalt, nickel and ruthenium. Gluconate is understood to mean gluconic acid in free form, in lactone form or in the form of a mixture of these two forms, in the form of a salt or in the form of an ester.
Thus, for example calcium gluconate, sodium gluconate and delta-gluconolactone are perfectly suitable. The catalyst is composed of ions of metals selected from cobalt, nickel and ruthenium, which can be added in the form of any divalent or trivalent salts of nickel and ruthenium. Cobalt salts are preferably used: e.g. cobalt acetate, cobalt acetylacetonate , cobalt halides, cobalt nitrate, cobalt sulfate, etc. are all fully applicable. The amount of the catalyst (cobalt, nickel or ruthenium salt) is 0.001-50%, preferably 0.002-20%, and more preferably 0.005-5%, with respect to the gluconate used, in the D -Erythrose has obtained good results both in terms of yield and purity.
Therefore, it is conceivable to integrate the process of biomass utilization, start from lignocellulose, obtain glucose, fructose and xylose through effective hydrolysis, and then apply this alkaline catalytic system, which has good application and industrialization prospects. The preparation of D erythrose by the above method has the characteristics of many kinds of suitable raw material sugars, wide range of initial sugar concentration, flexible heating method, wide range of catalyst alkalinity, single chirality, etc., easy operation, simple equipment, energy saving, and post-treatment Convenience, high conversion and selectivity.
Since D erythrose is currently considered to be one of the important platform compounds that can be obtained from biomass and has chirality, a series of products with a wide range of applications can be obtained through chiral transformation and achiral transformation. It can be used as an intermediate in fine chemicals and pharmaceuticals, and has huge economic value and broad application prospects. Therefore, this simple and efficient method for preparing a large amount of D erythrose from biomass sugar is expected to realize its large-scale industrial production.
FAQ
What is erythrose?
Erythrose is a tetrose saccharide with the chemical formula C4H8O4. It has one aldehyde group, and is thus part of the aldose family. The natural isomer is D-erythrose. It is a member of the class of compounds known as pentoses.
What type of sugar is D-erythrose?
D-Erythrose is a four-carbon sugar classified as an aldose. D-Erythrose has unique chemical properties that make it an important intermediate in various metabolic pathways, especially in the biosynthesis of amino acids and nucleotides.
What is the difference between D-erythrose and L-erythrose?
Definition: D-configuration is when the lowest chiral carbon of a sugar is similar to the R isomer of glyceraldehydes, while L-configuration is when the bottom chiral carbon of sugar is similar to the S isomer of glyceraldehyde.
Is D-erythrose optically active?
The (−) in its name implies that D−(−) -erythrose is optically active (levorotatory). When D- (-)-erythrose is reduced (using H2 and a nickel catalyst), it gives an optically inactive product of formula HOCH2−CH(OH)−CH(OH)−CH2OH.
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