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14131-42-1 , 4-Nitrophenyl 2,3,4,6-tetra-O-acetyl-a-D-glucopyranoside, CAS:14131-42-1

14131-42-1 , 4-Nitrophenyl 2,3,4,6-tetra-O-acetyl-a-D-glucopyranoside,
CAS:14131-42-1
C20H23NO12 / 469.4
MFCD04973639

4-Nitrophenyl 2,3,4,6-tetra-O-acetyl-a-D-glucopyranoside

4-Nitrophenyl 2,3,4,6-tetra-O-acetyl-a-D-glucopyranoside is a useful substrate for enzymatic assays. This high-sensitivity chromogenic pNP substrate offers enhanced selectivity and increased detection ability, allowing for a broad range of applications in the field of glycosidase research. Featuring rapid colorimetric readouts with easily detectable endpoint determination, this substrate delivers clear and accurate results every time.

4-Nitrophenyl 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranoside (NP-Glc) is a chromogenic and substrate used to detect enzymes that hydrolyze glycoside bonds. It is composed of a glucopyranoside molecule and a 4-nitrophenyl group, which together form a chromophore that absorbs light in the visible range. The molecule is commonly used in biochemistry and enzymology research to detect the presence of glycosidases and other enzymes that cleave glycosidic bonds.

Synthesis and Characterization:

NP-Glc can be synthesized by several methods, including chemical synthesis and enzymatic methods. One common method involves the acetylation of glucopyranose followed by conversion to the nitrophenyl derivative. The compound can be characterized by several techniques, including nuclear magnetic resonance (NMR), high-resolution mass spectrometry, and infrared spectroscopy.

Analytical Methods:

NP-Glc can be analyzed by several methods, including UV-Vis absorbance spectroscopy and HPLC. UV-Vis absorbance spectroscopy involves measuring the absorbance of the compound at a particular wavelength using a spectrophotometer. HPLC involves separating the compound from other components in a sample using a chromatographic column and then detecting it using a detector such as a UV-Vis detector.

Biological Properties:

NP-Glc is commonly used as a substrate for the detection of glycosidases and other enzymes. It has been used to detect the presence of enzymes in various organisms, including bacteria, fungi, and mammals.

Toxicity and Safety in Scientific Experiments:

NP-Glc is generally considered safe for use in scientific experiments, although it should be handled with care as it can be harmful if ingested or inhaled. Standard laboratory safety procedures should be followed when handling the compound.

Applications in Scientific Experiments:

NP-Glc has a wide range of applications in scientific experiments, including the detection of glycosidases and other enzymes in various organisms. It is also used in the synthesis and study of glycoside derivatives and other carbohydrate-related compounds.

Current State of Research:

Research on NP-Glc is ongoing, with several studies investigating its use in the detection of glycosidases and other enzymes and its potential use in the synthesis of carbohydrate-related compounds.

Potential Implications in Various Fields of Research and Industry:

NP-Glc has potential implications in various fields of research and industry, including biotechnology, pharmaceuticals, and food science. It can be used in the detection of enzymes in various organisms, including bacteria, fungi, and mammals, which has implications for the development of new diagnostic tools and therapies. It also has potential applications in the synthesis and study of carbohydrate-related compounds, which have applications in a wide range of industries.

Limitations and Future Directions:

Despite its potential applications, NP-Glc has several limitations, including its low solubility in water and its limited enzyme specificity. Future research may focus on improving the solubility and enzyme specificity of the compound and exploring its potential applications in various fields, including biotechnology, pharmaceuticals, and food science. Some of the potential future directions are:

1. Synthesis of NP-Glc derivatives with improved enzyme specificity.

2. Development of new analytical methods for the detection of enzymes using NP-Glc derivatives.

3. Investigation of the biochemical pathways involving the cleavage of glycosidic bonds and the potential role of NP-Glc in these pathways.

4. Study of the physiological and pathological implications of glycosidic bond cleavage in various organisms.

5. Development of new therapeutic agents based on the inhibition or activation of enzymes involved in glycosidic bond cleavage.

6. Study of the potential applications of NP-Glc derivatives in the food industry, such as the detection of contaminants or the modification of food properties.

7. Investigation of the potential applications of NP-Glc derivatives in the renewable energy industry, such as the synthesis of biofuels or biomaterials.

8. Study of the structural and functional properties of glycoside derivatives in various organisms and their potential applications in biotechnology and nanotechnology.

9. Investigation of the potential applications of NP-Glc derivatives in the treatment of diseases involving abnormal glycosylation, such as cancer and genetic diseases.

10. Development of new methods for the synthesis and purification of NP-Glc and its derivatives, with improved yields and lower costs.

CAS Number14131-42-1
Product Name4-Nitrophenyl 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranoside
IUPAC Name[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(4-nitrophenoxy)oxan-2-yl]methyl acetate
Molecular FormulaC20H23NO12
Molecular Weight469.4 g/mol
InChIInChI=1S/C20H23NO12/c1-10(22)28-9-16-17(29-11(2)23)18(30-12(3)24)19(31-13(4)25)20(33-16)32-15-7-5-14(6-8-15)21(26)27/h5-8,16-20H,9H2,1-4H3/t16-,17-,18+,19-,20+/m1/s1
InChI KeyBEUISCKWILNFIL-OBKDMQGPSA-N
SMILESCC(=O)OCC1C(C(C(C(O1)OC2=CC=C(C=C2)[N+](=O)[O-])OC(=O)C)OC(=O)C)OC(=O)C
Synonymsp-Nitrophenyl α-D-Glucopyranoside 2,3,4,6-Tetraacetate;
Canonical SMILESCC(=O)OCC1C(C(C(C(O1)OC2=CC=C(C=C2)[N+](=O)[O-])OC(=O)C)OC(=O)C)OC(=O)C
Isomeric SMILESCC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC2=CC=C(C=C2)[N+](=O)[O-])OC(=O)C)OC(=O)C)OC(=O)C


CAS No: 14131-42-1 Synonyms: p-Nitrophenyl 2,3,4,6-tetra-O-acetyl-a-D-glucopyranoside MDL No: MFCD04973639 Chemical Formula: C20H23NO12 Molecular Weight: 469.4


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