溴代葡萄糖四醋酸酯, Acetobromo-α-D-glucose

2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide (TAGB) is a carbohydrate derivative and a chemical reagent extensively used in glycochemistry as a glycosyl donor or acceptor in the synthesis of various oligosaccharide compounds. This paper aims to provide a comprehensive overview of TAGB, including its physical and chemical properties, synthesis, characterization, analytical methods, biological properties, toxicity, 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.

Definition and Background:

TAGB, also known as tetraacetylglucal bromide, is a glycosyl donor commonly used in organic chemistry and biochemistry research to synthesize glycosidic bonds between oligosaccharide compounds. The compound has the molecular formula C14H19BrO9 and a molecular weight of 429.20 g/mol. TAGB is a white crystalline powder, soluble in a mixture of chloroform and methanol, and poorly soluble in water. It is commercially available and widely used in glycochemistry research.

Physical and Chemical Properties:

TAGB is a crystalline solid with a white appearance and a melting point of 145-148°C. It is soluble in a mixture of chloroform and methanol, with a solubility of 10 mg/mL. It is poorly soluble in water, with a solubility of 0.1-1 mg/mL. The compound is stable at room temperature and can be stored for an extended period. TAGB is sensitive to moisture and light, which can cause degradation and loss of activity. The chemical structure of TAGB is shown in Figure 1.

Synthesis and Characterization:

TAGB is synthesized by the reaction of tetraacetylglucal with phosphorus tribromide (PBr3). The reaction takes place in anhydrous dichloromethane at room temperature, and the resulting product is purified by column chromatography. The characterization of TAGB is done by a combination of physical and chemical methods, including NMR spectroscopy, mass spectrometry, and infrared spectroscopy.

Analytical Methods:

The analytical methods used to determine the purity and identity of TAGB include High-performance liquid chromatography (HPLC), thin-layer chromatography (TLC), and nuclear magnetic resonance (NMR) spectroscopy. The purity of TAGB can be assessed by HPLC, which separates the compound from impurities. TLC is useful for monitoring the progress of TAGB synthesis by visualizing the compound on a silica gel plate. NMR spectroscopy is used to confirm the identity and purity of TAGB.

Biological Properties:

TAGB has limited biological activity and is not commonly used for medical purposes. However, studies have shown that it can inhibit the growth of certain bacteria and fungi. TAGB has also been used in the synthesis of oligosaccharide compounds that have biological activity.

Toxicity and Safety in Scientific Experiments:

TAGB is generally considered safe for use in scientific experiments. However, it is essential to handle the compound with care and wear appropriate protective equipment when working with it. TAGB is moderately toxic and can cause eye and skin irritation. The compound should not be ingested, inhaled, or allowed to come in contact with mucous membranes.

Applications in Scientific Experiments:

TAGB is widely used in glycochemistry research as a glycosyl donor or acceptor in synthesizing oligosaccharide compounds. The compound is also used in the synthesis of glycopeptides, glycoproteins, and carbohydrates with potential biological activity. TAGB is used to prepare glycosylated natural products and provides access to complex carbohydrate structures for biological studies.

Current State of Research:

Research on TAGB is ongoing, and there is a continued interest in its use as a glycosyl donor or acceptor in glycochemistry research. Studies are being conducted to develop more efficient and selective methods for the synthesis of oligosaccharides using TAGB. The compound is also being investigated for its use in the preparation of complex glycosylated natural products, glycopeptides, and glycoproteins.

Potential Implications in Various Fields of Research and Industry:

TAGB has implications in various fields, including medicine, biochemistry, and the food industry. The compound can be used in the synthesis of carbohydrate structures for the development of drugs. TAGB can also be utilized in producing glycosylated natural products, bioactive molecules, and functional foods.

Limitations and Future Directions:

Despite the broad applicability of TAGB in glycochemistry research, the compound has limitations, including lower reaction yields, increased reaction times, and low stereoselectivity. Future research should focus on overcoming these challenges and streamlining the synthesis process while maintaining high efficiency. Other future directions include the usage of TAGB in drug design and its application in synthetic glycobiology. Newer methodologies to generate and transform glycosides should also be developed, keeping the safety concerns in mind.

Conclusion:

TAGB is an essential glycosyl donor and acceptor used in glycochemistry research. The compound has physical and chemical properties, synthesis, characterization, analytical methods, biological properties, toxicity, 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. Understanding the properties and applications of TAGB will undoubtedly lead to new innovations and discoveries in the fields of biology, medicine, and the food industry.

Title: Acetobromglucose

CAS Registry Number: 572-09-8

CAS Name: a-D-Glucopyranosyl bromide 2,3,4,6-tetraacetate

Additional Names: a-acetobromoglucose; 2,3,4,6-tetraacetyl-a-D-glucopyranosyl bromide

Molecular Formula: C14H19BrO9

Molecular Weight: 411.20

Percent Composition: C 40.89%, H 4.66%, Br 19.43%, O 35.02%

Literature References: Prepd by the action of hydrogen bromide upon anhydrous glucose in acetic anhydride: Redemann, Niemann, Org. Synth. coll. vol. III, 11 (1955). See also Fischer, Ber. 49, 584 (1916); Freudenberg, Ber. 60, 241 (1927); Gattermann-Wieland, Praxis des Organischen Chemikers (de Gruyter, Berlin, 40th ed., 1961) p 340.

Properties: Crystals from isopropyl ether, mp 88-89°. [a]D19 +199.3° (c = 3 in chloroform); [a]D15 +230.3° (c = 9 in benzene). Best stored in a vacuum desiccator. Dec on contact with water. One gram dissolves in 20 ml absolute ethanol, more soluble in methanol. Freely sol in ether, chloroform, acetone, ethyl acetate, benzene. Slightly sol in petr ether.

Melting point: mp 88-89°

Optical Rotation: [a]D19 +199.3° (c = 3 in chloroform); [a]D15 +230.3° (c = 9 in benzene)

COA:

Product name: 2,3,4,6-O-Tetraacetyl-α-D-glucopyranosyl Bromide

M.F.: C₁₄H₁₉BrO₉                 M.W._: 411.2                  CAS: 572-09-8

References:

1. Mota JF, Guzman JFB, et al., Carbohydr. Res. 1992, Vol232, No1, p47-57