D-纖維二糖, D-Cellobiose

D-(+)-Cellobiose is a disaccharide consisting of two D-glucose units linked by a β(1→4) glycosidic bond. It is commonly found in cellulose, hemicelluloses, and plant cell walls. D-(+)-Cellobiose has been extensively studied due to its potential applications in the field of science, specifically in the production of biofuels. This paper provides an overview of the definition and background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions of D-(+)-Cellobiose.

Definition and Background

D-(+)-Cellobiose is a type of disaccharide, which is a molecule that consists of two monosaccharides linked by a glycosidic bond. Monosaccharides are simple sugars that cannot be broken down into simpler molecules by hydrolysis. D-(+)-Cellobiose is made up of two D-glucose molecules linked by a β(1→4) glycosidic bond. It is commonly found in cellulose, which is the main component of plant cell walls.

Physical and Chemical Properties

D-(+)-Cellobiose is a white crystalline solid that is soluble in water but insoluble in most organic solvents. It has a melting point of 187-189°C and a specific rotation of +27.0° (c=1, water). D-(+)-Cellobiose is a reducing sugar, which means that it can undergo oxidation-reduction reactions. Its chemical formula is C12H22O11, and its molecular weight is 342.30 g/mol.

Synthesis and Characterization

D-(+)-Cellobiose can be synthesized through the hydrolysis of cellulose or by the enzymatic breakdown of cellulose using cellobiase. The synthesis of D-(+)-Cellobiose can also be achieved through chemical reactions. The most commonly used methodology is through the transglycosylation of β-glucosidase.

D-(+)-Cellobiose can be characterized using various techniques, including chromatography, Fourier transform infrared (FTIR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, and X-ray crystallography. FTIR spectroscopy provides information on the functional groups in D-(+)-Cellobiose, while NMR spectroscopy gives detailed information about the chemical environment of each atom in the molecule. X-ray crystallography determines the exact three-dimensional structure of the molecule.

Analytical Methods

Various analytical methods have been used to determine the purity and concentration of D-(+)-Cellobiose. These methods include high-performance liquid chromatography (HPLC), gas chromatography (GC), and mass spectrometry (MS). HPLC and GC can be used to separate and analyze the components of a sample, while MS can be used to identify the molecular weight and structural information of a compound.

Biological Properties

D-(+)-Cellobiose has low biological activity and is not easily metabolized by most organisms. However, it can be hydrolyzed by cellobiase into two glucose molecules. In addition, D-(+)-Cellobiose has been shown to have potential prebiotic effects, meaning that it can selectively stimulate the growth and activity of beneficial microorganisms in the gut.

Toxicity and Safety in Scientific Experiments

D-(+)-Cellobiose is generally considered safe for scientific experiments. However, a study conducted in rats showed that high doses of D-(+)-Cellobiose can lead to weight loss, diarrhea, and changes in gut microbiota. It is important to note that the safety of D-(+)-Cellobiose in human consumption has not been fully established, but at present the consumption of small quantities is unlikely to have any adverse effects.

Applications in Scientific Experiments

D-(+)-Cellobiose has several potential applications in the field of science, specifically in the production of biofuels. It can be used as a substrate for the production of biofuels such as ethanol and butanol. In addition, D-(+)-Cellobiose can be used as a growth substrate for microorganisms, which can be used to produce other valuable products such as enzymes, proteins, and antibiotics.

Current State of Research

D-(+)-Cellobiose is a widely studied disaccharide due to its potential applications in the field of science. Research has focused on the production of biofuels and the prebiotic effects of D-(+)-Cellobiose. Many studies have investigated the use of different microorganisms and enzymes for the conversion of D-(+)-Cellobiose into biofuels. In addition, research has shown that D-(+)-Cellobiose has potential prebiotic effects that can promote gut health.

Potential Implications in Various Fields of Research and Industry

D-(+)-Cellobiose has potential implications in various fields of research and industry. In the field of biochemistry, D-(+)-Cellobiose can be used as a substrate for studying the structure and function of enzymes involved in the breakdown of cellulose. In the field of agriculture, D-(+)-Cellobiose can be used as a natural fertilizer to improve soil quality and promote plant growth. In the field of medicine, D-(+)-Cellobiose can be used as a prebiotic supplement to promote gut health.

Limitations and Future Directions

Despite its potential applications, there are some limitations to the use of D-(+)-Cellobiose in scientific experiments. The synthesis of D-(+)-Cellobiose can be expensive and time-consuming, and its use requires specialized equipment and expertise. In addition, the safety and toxicity of D-(+)-Cellobiose in human consumption have not been fully established.

Future research should focus on overcoming these limitations and exploring new applications of D-(+)-Cellobiose in various fields. Studies can be conducted to optimize the synthesis of D-(+)-Cellobiose and evaluate its safety in human consumption. New research can also investigate the use of D-(+)-Cellobiose in the production of other valuable products, such as pharmaceuticals and chemicals. Furthermore, future directions could focus on the role of D-(+)-Cellobiose in sustainable development and renewable energy.

COA:

Product name: D-Cellobiose, 4-beta-D-glucopyransoyl-D-glucopyranose

CAS: 528-50-7           M.F.: C₁₂H₂₂O₁₁      M.W.: 342.3

Title: Cellobiose

CAS Registry Number: 528-50-7

CAS Name: 4-O-b-D-Glucopyranosyl-D-glucose

Additional Names: b-cellobiose; cellose; 4-(b-D-glucosido)-D-glucose

Molecular Formula: C12H22O11

Molecular Weight: 342.30

Percent Composition: C 42.11%, H 6.48%, O 51.41%

Literature References: Unit of cellulose and lichenin. Does not occur free in nature, or as glucoside. Prepn from cotton: Braun, Org. Synth. coll. vol. II, 122, 124 (1943). Prepn from cell-free enzymatic hydrolyzate of cellulose: Whistler, Smart, J. Am. Chem. Soc. 75, 1916 (1953). Structure: Haworth, Hirst, J. Chem. Soc. 119, 193 (1923); Charlton et al., ibid. 1926, 89; Zemplén, Ber. 59, 1254 (1926); Haworth et al., J. Chem. Soc. 1927, 2809; Peterson, Spencer, J. Am. Chem. Soc. 49, 2822 (1927); Helferich et al., Ber. 63, 992 (1930); Hess, Dziengel, ibid. 68, 1594 (1935); Hassid, Ballou in The Carbohydrates, W. Pigman, Ed. (Academic Press, New York, 1957) p 490. Synthesis: Haskins et al., J. Am. Chem. Soc. 64, 1289 (1942). Review: Pazur in The Carbohydrates vol. 2A, W. Pigman et al., Eds. (Academic Press, New York, 2nd ed., 1970) pp 109-110; R. G. Edwards, Dev. Food Carbohydr. 2, 229-273 (1980).

Properties: Minute crystals from dil alcohol which retain 0.25 to 0.50 mol water after drying in vacuo. Indifferent taste. Dec 225°. Shows mutarotation. [a]D20 +14.2° ? +34.6° (15 hrs, c = 8). One gram dissolves in 8 ml water, in 1.5 ml boiling water. Almost insol in abs alc and ether. Reduces Fehling's soln. Hydrolysis with acid or emulsin yields 2 mols b-D-glucose. Not fermented by brewers' yeast, maltase, or invertase.

Optical Rotation: [a]D20 +14.2° ? +34.6° (15 hrs, c = 8)

Derivative Type: Octaacetyl-aldehydro-cellobiose

Molecular Formula: C28H38O19

Molecular Weight: 678.59

Percent Composition: C 49.56%, H 5.64%, O 44.80%

Properties: mp 105-110°. [a]D20 +17.7° (c = 3 in chloroform).

Melting point: mp 105-110°

Optical Rotation: [a]D20 +17.7° (c = 3 in chloroform)

Derivative Type: Octaacetyl-a-cellobiose

Molecular Formula: C28H38O19

Molecular Weight: 678.59

Percent Composition: C 49.56%, H 5.64%, O 44.80%

Properties: mp 229°. [a]D20 +41° (c = 6 in chloroform).

Melting point: mp 229°

Optical Rotation: [a]D20 +41° (c = 6 in chloroform)

Derivative Type: Octaacetyl-b-cellobiose

Properties: mp 202°. [a]D20 -14.7° (c = 5 in chloroform).

Melting point: mp 202°

Optical Rotation: [a]D20 -14.7° (c = 5 in chloroform)

D-Cellobiose is a disaccharide that consists of two β-glucose molecules linked by a β-1,4 glycosidic bond. It can be used as a substrate of β-glucosidase.

Cellobiose, also known as GLCB1-4GLCB or cellose, belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Cellobiose exists as a solid, soluble (in water), and a very weakly acidic compound (based on its pKa). Cellobiose has been found in human intestine and spleen tissues. Within the cell, cellobiose is primarily located in the cytoplasm. Cellobiose exists in all eukaryotes, ranging from yeast to humans.

Beta-cellobiose is a cellobiose with beta configuration at the reducing-end glucose residue. It has a role as an epitope.

A disaccharide consisting of two glucose units in beta (1-4) glycosidic linkage. Obtained from the partial hydrolysis of cellulose.

References:

1. Pitson SM, et al., Enzyme Microbiol. Technol. 1997, 21, p182
2. Beil. 17/7, V, 191