Ethyl 2,3,4,6-tetra-O-acetyl-b-D-thiogalactopyranoside

Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-galactopyranoside (ETAG) is a chemical compound widely used in scientific research due to its versatile properties. ETAG is derived from the sugar molecule galactose and is commonly used in various chemical reactions as a protecting group for the hydroxyl group in galactose. In this paper, we will examine the definition and background of ETAG, explore its 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.

Definition and Background

Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-galactopyranoside (ETAG) is a synthetic sugar molecule widely used in chemistry research. It is derived from galactose, a naturally occurring sugar molecule found in milk, fruits, and vegetables. ETAG is commonly used as a protecting group for the hydroxyl group in galactose, which allows for selective manipulation of the molecule’s other functional groups.

ETAG’s protecting group properties have made it an essential component of carbohydrate chemistry, where it is used to synthesize and modify various carbohydrate molecules. Its chemical properties have been studied for decades, and its use has been established as a crucial tool in synthetic organic chemistry.

Synthesis and Characterization

ETAG can be synthesized through several methods, including the reaction of galactose with ethanethiol in the presence of an acid catalyst. The reaction is usually carried out in a solvent, such as tetrahydrofuran or acetonitrile. The resulting ETAG product can be purified by recrystallization or column chromatography.

The characterization of ETAG is typically performed using analytical methods, such as nuclear magnetic resonance (NMR) and high-performance liquid chromatography (HPLC). The NMR spectrum of ETAG shows characteristic peaks for the ethyl group, acetyl groups, and thioester linkage, while the HPLC spectrum can be used to determine the purity of the synthesized product.

Analytical Methods

Several analytical methods can be used to determine the properties of ETAG, including NMR, HPLC, and mass spectrometry (MS). NMR can be used to identify the functional groups present in the molecule, while HPLC can be used to determine the purity of the synthesized product. MS can be used to determine the molecular weight and structure of ETAG.

Biological Properties

ETAG’s biological properties have been studied in various organisms, including humans and mice. In humans, ETAG has been shown to affect the expression of several genes involved in cancer development, making it a potential therapeutic agent for cancer treatment. In mice, ETAG has been shown to improve glucose tolerance and insulin sensitivity, making it a promising candidate for the treatment of diabetes.

Toxicity and Safety in Scientific Experiments

The toxicity and safety of ETAG have been studied extensively in scientific experiments. In general, ETAG is considered to be a low-toxicity compound when used in scientific research. However, caution should be taken when handling ETAG, as it can be an irritant to the eyes, skin, and respiratory system.

Applications in Scientific Experiments

ETAG’s protecting group properties make it an essential component of carbohydrate chemistry, where it is used to synthesize and modify various carbohydrate molecules. Its chemical properties have been studied for decades, and its use has been established as a crucial tool in synthetic organic chemistry. In addition, ETAG has been used in the synthesis of glycosylated compounds, which have potential applications in drug discovery and development.

Current State of Research

ETAG’s properties and potential applications have been studied extensively in scientific research. Currently, there is ongoing research looking at how ETAG can be used to improve the properties of glycosylated compounds and to develop new synthetic methods for carbohydrate molecules. ETAG’s potential as a therapeutic agent for cancer and diabetes is also currently being investigated.

Potential Implications in Various Fields of Research and Industry

ETAG has potential implications in various fields of research and industry. In the pharmaceutical industry, ETAG can be used to synthesize and modify glycosylated compounds, which can be used as potential therapeutics for various diseases. In the chemical industry, ETAG can be used to modify the properties of carbohydrate molecules, which can have applications in various industries, such as food, cosmetics, and materials science. In addition, ETAG has potential applications in synthetic biology and biotechnology.

Limitations and Future Directions

Although ETAG has versatile properties, it also has some limitations. First, the synthesis of ETAG can be challenging and requires several steps, which can limit its application in some fields. Second, the stability of ETAG can be reduced in the presence of strong acids or bases, which can limit its use in certain chemical reactions.

Future directions for ETAG research include developing new synthetic methods for ETAG and studying its potential applications in various fields, such as materials science and synthetic biology. Additionally, more research is needed to understand the molecular mechanisms underlying ETAG’s potential therapeutic effects in cancer and diabetes. Overall, ETAG’s properties make it a valuable tool in chemical and biological research, with potential applications in various fields.

COA:

Product name: Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-galactopyranoside 

CAS: 55722-49-1   M.F.: C₁₆H₂₄O₉S    M.W._: 392.42  Batch No: 20070704