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  • 425427-87-8, 6-氯-3-吲哚beta-D-纤维二糖苷, CAS:425427-87-8
425427-87-8, 6-氯-3-吲哚beta-D-纤维二糖苷, CAS:425427-87-8

425427-87-8, 6-氯-3-吲哚beta-D-纤维二糖苷, CAS:425427-87-8

425427-87-8,6-氯-3-吲哚beta-D-纤维二糖苷,
6-Chloro-3-indolyl beta-D-cellobioside,
CAS:425427-87-8
C20H26ClNO11 / 491.87
MFCD00467205

6-Chloro-3-indolyl b-D-cellobioside

6-氯-3-吲哚beta-D-纤维二糖苷

6-Chloro-3-indolyl b-D-cellobioside (6CI) is a transcription factor that regulates gene expression and belongs to the family of plant cell wall biosynthesis related proteins. It has been shown to be involved in the regulation of genes encoding for enzymes involved in the synthesis of cell wall components such as cellulose, pectin, and xylan. 6CI is regulated by environmental factors and cellular stresses mediated by changes in its expression levels. 6CI also has a role in controlling gene expression profiles, which are used for profiling purposes.

6-Chloro-3-indoxyl-beta-D-cellobioside, also known as X-Cel, is a chemical compound used in scientific experiments as a substrate for the assay of cellobiohydrolases. It is a member of the indoxyl-beta-D-glycosides, which are chromogenic substrates that are commonly used in the detection of enzymes.

Definition and Background:

6-Chloro-3-indoxyl-beta-D-cellobioside is a chromogenic substrate that is cleaved by cellobiohydrolases to produce a blue-colored product. Cellobiohydrolases are glycosyl hydrolases that play a critical role in the hydrolysis of cellulose into glucose. The use of 6-Chloro-3-indoxyl-beta-D-cellobioside as a substrate allows for the measurement of cellobiohydrolase activity in a variety of scientific experiments.

Physical and Chemical Properties:

6-Chloro-3-indoxyl-beta-D-cellobioside is a relatively stable compound that is soluble in water and organic solvents such as methanol, ethanol, and acetonitrile. It has a melting point of 175-180°C and a chemical formula of C26H31ClN2O10.

Synthesis and Characterization:

6-Chloro-3-indoxyl-beta-D-cellobioside can be synthesized by the reaction of indole with 6-chloro-6-deoxy-beta-cellobiosyl bromide. The resulting product is purified through a series of column chromatography techniques, and its structure is confirmed through the use of nuclear magnetic resonance spectroscopy and mass spectrometry.

Analytical Methods:

6-Chloro-3-indoxyl-beta-D-cellobioside is typically analyzed using UV-Vis spectrophotometry, which allows for the measurement of the absorbance of the blue-colored product produced by the reaction with cellobiohydrolases.

Biological Properties:

6-Chloro-3-indoxyl-beta-D-cellobioside is not known to have any direct biological activity on cells or tissues. Its use is strictly limited to scientific experiments as a substrate for the measurement of enzyme activity.

Toxicity and Safety in Scientific Experiments:

6-Chloro-3-indoxyl-beta-D-cellobioside is generally considered to be safe for use in scientific experiments. However, like any chemical compound, it should be handled with care and appropriate safety measures should be taken to prevent exposure.

Applications in Scientific Experiments:

6-Chloro-3-indoxyl-beta-D-cellobioside is primarily used as a substrate for the measurement of cellobiohydrolase activity in a variety of scientific experiments. It has also been used in the detection of other glycosyl hydrolases, such as endoglucanases.

Current State of Research:

6-Chloro-3-indoxyl-beta-D-cellobioside is a well-established substrate that is widely used in the scientific community. However, ongoing research is focused on the development of new and improved substrates for the measurement of enzyme activity.

Potential Implications in Various Fields of Research and Industry:

The use of 6-Chloro-3-indoxyl-beta-D-cellobioside as a substrate has implications for a variety of fields, including biotechnology, biofuels, and environmental science. As the demand for renewable energy sources increases, research into the efficient hydrolysis of cellulose is becoming increasingly important.

Limitations and Future Directions:

Despite its widespread use, 6-Chloro-3-indoxyl-beta-D-cellobioside has several limitations that make it less than ideal for certain applications. These limitations include a narrow pH range, low stability at elevated temperatures, and sensitivity to certain metal ions. Future research is focused on the development of new substrates that are more stable and adaptable to a wider range of experimental conditions. Some potential future directions for research include:

1. Development of new substrates with improved stability and reproducibility

2. Identification of new enzymes that could potentially hydrolyze cellulose more efficiently

3. Investigation of the potential use of 6-Chloro-3-indoxyl-beta-D-cellobioside and other substrates for the detection of other glycosyl hydrolases

4. Exploration of the potential use of 6-Chloro-3-indoxyl-beta-D-cellobioside and other substrates in the production of biofuels and other industrial applications.

CAS Number425427-87-8
Product Name6-Chloro-3-indoxyl-beta-D-cellobioside
IUPAC Name(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-[(6-chloro-1H-indol-3-yl)oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular FormulaC20H26ClNO11
Molecular Weight491.9 g/mol
InChIInChI=1S/C20H26ClNO11/c21-7-1-2-8-9(3-7)22-4-10(8)30-19-17(29)15(27)18(12(6-24)32-19)33-20-16(28)14(26)13(25)11(5-23)31-20/h1-4,11-20,22-29H,5-6H2/t11-,12-,13-,14+,15-,16-,17-,18-,19-,20+/m1/s1
InChI KeyLPDLZDNDKZIJNA-NQXZFOFXSA-N
SMILESC1=CC2=C(C=C1Cl)NC=C2OC3C(C(C(C(O3)CO)OC4C(C(C(C(O4)CO)O)O)O)O)O
Canonical SMILESC1=CC2=C(C=C1Cl)NC=C2OC3C(C(C(C(O3)CO)OC4C(C(C(C(O4)CO)O)O)O)O)O
Isomeric SMILESC1=CC2=C(C=C1Cl)NC=C2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O


CAS No: 425427-87-8 Synonyms: Salmon-cellobioside MDL No: MFCD00467205  Chemical Formula: C20H26ClNO11 Molecular Weight: 491.87

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