5-Thio-D-glucose

5-Thio-D-Glucose is a sulfur analog of D-glucose, a simple sugar found in the human diet and biosphere. Also known as 5-thio-D-glucopyranose, it exhibits significant differences from glucose in its chemical, physical, and biological properties. This compound has been actively studied by scientists and pharmacologists for its potential application in various fields of research and industry, including medicinal chemistry, biotechnology, and environmental science.

Physical and Chemical Properties:

5-Thio-D-Glucose is a stable crystalline solid with a molecular formula C6H12O5S. It has a molar mass of 196.22 g/mol . It is soluble in water and ethanol, but insoluble in ether and chloroform. The compound shows a distinctive conformational feature and strong donor-acceptor hydrogen bonding, resulting in significant changes in its physical and chemical properties.

Synthesis and Characterization:

5-Thio-D-Glucose can be synthesized by various methods, including the addition of thioglycosyl-accepting reagent to a glycosyl donor, glycosylation of a thioglycoside donor, or by enzymatic methods. The compound has been characterized using techniques such as NMR spectroscopy, X-ray crystallography, and mass spectrometry.

Analytical Methods:

Several analytical methods have been developed to quantify 5-Thio-D-Glucose in various biological and environmental samples. These methods include the use of high-performance liquid chromatography (HPLC), gas chromatography (GC), and capillary electrophoresis (CE).

Biological Properties:

5-Thio-D-Glucose exhibits diverse biological properties, including antiviral, antitumor, and antibacterial activities. It inhibits the growth of tumor cells in vitro and in vivo by inducing apoptosis, cell cycle arrest, and DNA damage. The compound also acts as an inhibitor of glycogen phosphorylase, a key enzyme in glucose metabolism, making it a potential drug candidate for the treatment of diabetes and other metabolic disorders.

Toxicity and Safety in Scientific Experiments:

Studies have shown that 5-Thio-D-Glucose has low toxicity and is safe for use in scientific experiments. However, its potential toxicity and safety concerns in human consumption and environmental exposure require further investigation.

Applications in Scientific Experiments:

The unique properties of 5-Thio-D-Glucose make it an attractive molecule for various applications in scientific experiments. It has been utilized as a probe to study glycogen metabolism, as a tool to map glycosylation patterns on proteins, and as a precursor in the synthesis of novel drugs and antimicrobial agents.

Current State of Research:

The ongoing research on 5-Thio-D-Glucose is mainly focused on its therapeutic potential as an antitumor and antiviral agent, as well as its role in glycogen metabolism and glycosylation pathways. Several studies have been conducted to investigate the compound’s mechanisms of action, potency, and toxicity, with promising results.

Potential Implications in Various Fields of Research and Industry:

The unique properties and potential applications of 5-Thio-D-Glucose can have significant implications in various fields of research and industry. In medicinal chemistry, it can be used to develop novel drugs for the treatment of cancer and metabolic disorders. In biotechnology, it can be applied as a tool in biomedical research and drug discovery. In environmental science, it can be used in the development of eco-friendly and sustainable technologies for the management of pollution and waste.

Limitations and Future Directions:

Despite its promising potential, 5-Thio-D-Glucose also has limitations and challenges that need to be addressed in future research. These include its low solubility, limited scalability, and potential toxicity concerns. Future research can focus on developing new synthesis methods, improving its solubility and bioavailability, and investigating its long-term safety and environmental impact.

Future Directions:

1. Development of novel delivery methods for 5-Thio-D-Glucose, such as nanoparticles and liposomes, to improve its bioavailability.

2. Investigation of the role of 5-Thio-D-Glucose in other metabolic pathways and its potential for the treatment of other metabolic disorders.

3. Exploration of the potential of 5-Thio-D-Glucose in the field of immunotherapy for cancer treatment.

4. Synthesis of novel derivatives of 5-Thio-D-Glucose with improved potency and selectivity against cancer cells.

5. Investigation of the potential of 5-Thio-D-Glucose as a scaffold for the development of glycosylated biomimetics.

6. Evaluation of the environmental impact and long-term safety of 5-Thio-D-Glucose in human consumption and waste management.

7. Exploration of the use of 5-Thio-D-Glucose in the development of novel antimicrobial agents.

8. Development of efficient and scalable methods for the synthesis of 5-Thio-D-Glucose and its derivatives.

Title: 5-Thio-D-glucose

CAS Registry Number: 20408-97-3

CAS Name: 5-Thio-a-D-glucopyranose

Additional Names: a-D-glucothiopyranose

Molecular Formula: C6H12O5S

Molecular Weight: 196.22

Percent Composition: C 36.73%, H 6.16%, O 40.77%, S 16.34%

Literature References: The nearest analog of normal D-glucose available to date. Thought to interfere with cellular transport systems utilizing D-glucose due to this structural similarity. The first chemical other than a hormone or alkylating agent which can interfere reversibly with spermatogenesis and which also has been effective against malignant cultured cells. Prepn: M. S. Feather, R. L. Whistler, Tetrahedron Lett. 1962, 667; Rowell, Whistler, J. Org. Chem. 31, 1514 (1966); U. G. Nayak, R. L. Whistler, ibid. 34, 97 (1969); Abd El-Rahman, Whistler, Org. Prep. Proced. Int. 5, 245 (1973); H. Driguez, B. Henrissat, Tetrahedron Lett. 22, 5061 (1981). Pharmacology: D. J. Hoffman, R. L. Whistler, Biochemistry 7, 4479 (1968); R. L. Whistler, W. C. Lake, Biochem. J. 130, 919 (1972). Radioprotective effect on tissue in vivo: V. L. Schuman et al., Int. J. Radiat. Oncol. Biol. Phys. 8, 589 (1982). Brief review: Science 186, 431 (1974).

Properties: Crystals from methanol, mp 135-136?. [a]D20 +188? (c = 1.56 in water). LD50 i.p. in mice: 5.5 g/kg (Schuman).

Melting point: mp 135-136?

Optical Rotation: [a]D20 +188? (c = 1.56 in water)

Toxicity data: LD50 i.p. in mice: 5.5 g/kg (Schuman)

Use: Tool for examination of D-glucose biochemistry.

Product name: 5-Thio-D-glucose, predominantly alpha-anomer

M.F.: C₆H₁₂O₅S                 M.W._: 196.22                CAS: 20408-97-3  

References:

1. Cantour-Galcera M-O, Ortiz-Mellet C, Defaye J, Carhohydr. Res. 1996, 281, p119