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80951-92-4 , Thiocellobiose, CAS:80951-92-4

80951-92-4 , Thiocellobiose,
CAS:80951-92-4
C12H22O10S / 358.362
MFCD00270082

硫代纤维二糖, hiocellobiose

Thiocellobiose is a disaccharide comprised of two glucose units connected by a β1-4 glycosidic bond, with sulfur replacing the sixth carbon atom of the non-reducing glucose. Thiocellobiose is soluble in water, methanol, and ethanol but insoluble in ether and chloroform. In 1951, researchers identified it as a partial cellulase inhibitor present in the culture liquid of Cellvibrio celluloseum.

Synthesis and Characterization

Thiocellobiose can be synthesized by reacting cellobiose with 2-chloroethanesulfonyl chloride in pyridine. It can also be produced enzymatically by the use of Escherichia coli or through cellobiose phosphorylase-mediated enzymatic coupling of glucosyl-SO_3^– with glucose.

Analytical Methods

The quantification and characterization of thiocellobiose are performed by using chromatographic or spectroscopic methods. High-performance liquid chromatography (HPLC) coupled with ultraviolet-visible detectors (UV-Vis) is commonly used to measure thiocellobiose concentration in culture supernatants. Infrared (IR) spectroscopy and nuclear magnetic resonance (NMR) spectroscopy can be used for its characterization.

Biological Properties

Thiocellobiose is used as a substrate for cellobiose phosphorylase, a glycoside hydrolase that catalyzes the reversible phosphorolysis of β-glucosides to produce glucose 1-phosphate and glucose. Thiocellobiose also acts as an inhibitor of cellobiohydrolases and other cellulase enzymes.

Toxicity and Safety in Scientific Experiments

Thiocellobiose has been classified as a non-toxic compound for animal studies, and no harmful side effects have been reported. In studies where it is used as a substrate or inhibitor, concentrations are kept below the threshold to minimize potential adverse effects on the animals.

Applications in Scientific Experiments

Thiocellobiose's unique properties and applications have made it useful in numerous scientific fields. It has been used as a substrate for cellobiose phosphorylase in protein engineering and enzyme kinetics studies. Thiocellobiose has been shown to efficiently inhibit endoglucanase enzymes, resulting in its use as a precursor to develop new inhibitors.

Current State of Research

There is ongoing research into the synthesis and characterization of thiocellobiose and its potential applications in various scientific fields. The use of thiocellobiose substrates and inhibitors in synthetic biology, biotechnology, and the pharmaceutical industry is an active area of research.

Potential Implications in Various Fields of Research and Industry

Thiocellobiose has the potential for numerous applications in various scientific fields and industries. Its use as a substrate in protein engineering will allow the creation of enzymes with enhanced catalytic properties. Thiocellobiose's inhibition of cellulose is valuable for developing new treatments for cellulose-related diseases such as obesity, cancer, and diabetes.

Limitations and Future Directions

The combination of thiocellobiose with other molecules, as well as evaluating its potential toxicity and antagonistic effects, are areas that require further examination. Future research that investigates the catalyst's molecular mechanisms and the wide-ranging applications that could emerge will serve as a foundation for its broader use.

Future Directions

The following research areas have the potential to unleash the full potential of thiocellobiose in research and industry:

1. Examination of its potential as a substrate for β-glucosidase to produce high-value metabolites

2. Investigation of thiocellobiose’s potential in crop improvement via cell wall manipulation

3. Examining its potential as a cell-penetrating synthetic sugar

4. Studying the effect of thiocellobiose in aiding microbial consortia in cellulose degradation.

Conclusion

Thiocellobiose is an important disaccharide derivative with a sulfur replacement in glucose's sixth carbon atom, making it a vital tool in a variety of scientific research and industries. It has unique physical and chemical properties, which make it a unique catalyst for numerous applications. The future of research into thiocellobiose is immense, as there is potential for further development in many fields, as outlined in the future directions section.

Competitive inhibitor of β-glucosidase from Streptomyces sp. and Paenibacillus polymyxa, occupying enzyme’s aglycone-binding site.  The compound is also a potent inducer of cellulase and other lignin-degrading enzymes in Schizophyllum commune.

CAS Number

80951-92-4

Product Name

Thiocellobiose

IUPAC Name

(2R,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylhexanal

Molecular Formula

C12H22O10S

Molecular Weight

358.36 g/mol

InChI

InChI=1S/C12H22O10S/c13-1-4(16)7(18)11(5(17)2-14)23-12-10(21)9(20)8(19)6(3-15)22-12/h1,4-12,14-21H,2-3H2/t4-,5+,6+,7+,8+,9-,10+,11+,12-/m0/s1

InChI Key

VMEDEPBFFWJMMG-WELRSGGNSA-N

SMILES

C(C1C(C(C(C(O1)SC(C(CO)O)C(C(C=O)O)O)O)O)O)O

Synonyms

Glc1S1-b-4Glc; 4-S-β-D-Glucopyranosyl-4-thio-D-glucose;

Canonical SMILES

C(C1C(C(C(C(O1)SC(C(CO)O)C(C(C=O)O)O)O)O)O)O

Isomeric SMILES

C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)S[C@H]([C@@H](CO)O)[C@@H]([C@H](C=O)O)O)O)O)O)O


CAS No: 80951-92-4 MDL No: MFCD00270082 Chemical Formula: C12H22O10S Molecular Weight: 358.362

References: 1. J. Bacteriol. 1982, 149, 47-532. Hamacher K, Carbohydr. Res. 1984


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