29781-32-6 , 4-Nitrophenyl 3,4-O-isopropylidene-a-D-galactopyranoside,
Cas:29781-32-6
C15H19NO8 / 341.31
MFCD15145076
4-Nitrophenyl 3,4-O-isopropylidene-a-D-galactopyranoside is a chemiluminescent substrate for detecting beta-galactosidase activity in bacteria. This product is a high purity, high quality compound that can be used as a culture media and environmental testing agent. It has been shown to be effective in diagnostics, chromogenic substrate, and enzyme substrate reactions. 4NPPG has been shown to be a fluorogenic substrate for beta-galactosidase assay and can be used as food testing agent with conjugate.
Definition and Background
4-Nitrophenyl 3,4-O-isopropylidene-a-D-galactopyranoside, also known as NPG and nitrophenylgalactoside, is a colorless crystalline powder that has become an important substrate in a variety of scientific experiments. Discovered by John H. Beynon and Jennie C. Williams in 1946, NPG is a non-toxic and stable compound that has found widespread use in the determination of enzyme activity, particularly those of beta-galactosidase.
Analytical Methods
Several analytical methods have been developed for the detection and quantification of 4-Nitrophenyl 3,4-O-isopropylidene-a-D-galactopyranoside in various biological matrices. These methods include, but are not limited to, spectrophotometry, high-performance liquid chromatography (HPLC), capillary electrophoresis (CE), and mass spectrometry (MS). Spectrophotometry is the most widely used method for measuring NPG hydrolysis, and it involves the monitoring of the formation of 4-nitrophenol at 400 nm.
Biological Properties
4-Nitrophenyl 3,4-O-isopropylidene-a-D-galactopyranoside has been shown to be a substrate for various enzymes such as beta-galactosidase and alpha-L-fucosidase. Its hydrolysis by beta-galactosidase produces 4-nitrophenol and galactose, while its hydrolysis by alpha-L-fucosidase produces 4-nitrophenol and L-fucose. These reactions have been widely used in the determination of enzyme activity and protein expression.
Toxicity and Safety in Scientific Experiments
4-Nitrophenyl 3,4-O-isopropylidene-a-D-galactopyranoside has been shown to be non-toxic and safe for use in scientific experiments. However, caution should be exercised when handling NPG in bulk as it may cause skin and eye irritation. Proper protective measures such as gloves, safety glasses, and laboratory coats should be worn at all times when working with NPG.
Applications in Scientific Experiments
4-Nitrophenyl 3,4-O-isopropylidene-a-D-galactopyranoside has found widespread use in various scientific experiments. It has been used in the determination of enzyme activity, protein expression, carbohydrate analysis, screening of synthetic compounds, and in the development of diagnostic assays. Its ease of use and reliability has made it an essential tool in the fields of biochemistry, biotechnology, and molecular biology.
Current State of Research
Research on 4-Nitrophenyl 3,4-O-isopropylidene-a-D-galactopyranoside is ongoing, and new applications for this compound continue to be discovered. Recent developments include the use of NPG in the detection of bacterial viability, the screening of synthetic compounds for hepatotoxicity, and the detection of human glycosidases in clinical samples.
Potential Implications in Various Fields of Research and Industry
The properties of 4-Nitrophenyl 3,4-O-isopropylidene-a-D-galactopyranoside make it an attractive compound for use in various fields of research and industry. Its non-toxicity, stability, and ease of use make it a valuable tool for the development of diagnostic assays and high-throughput screening applications. Its use in the detection of bacterial viability has potential implications in the field of microbiology, while its use in the screening of synthetic compounds for hepatotoxicity has potential implications in drug development.
Limitations and Future Directions
Despite its wide use, there are limitations to the use of 4-Nitrophenyl 3,4-O-isopropylidene-a-D-galactopyranoside. Its hydrolysis products (4-nitrophenol and galactose or L-fucose) may interfere with some assays, and its hydrolysis rate may differ from that of endogenous substrates. Future directions include the development of new analogs of NPG that can mimic endogenous substrates and the refinement of the analytical methods used to detect and quantify NPG in biological samples.
List of Future Directions:
- Development of NPG analogs that mimic endogenous substrates
- Refinement of the analytical methods used to detect and quantify NPG in biological samples
- Improvement of substrate specificity and sensitivity for NPG in different enzymes
- Exploration of the potential of NPG in the development of novel diagnostic assays for different diseases
- Investigation of the effect of different reaction conditions on the hydrolysis rate of NPG by different enzymes
- Development of new applications for NPG in the fields of biotechnology and materials science
- Use of NPG as a tool for the detection of different glycosylated molecules
- Development of NPG-based biosensors for the detection of various biomolecules
- Identification of new enzymes that can hydrolyze NPG
- Investigation of the mechanism of action of NPG and its hydrolysis products.
CAS Number | 29781-32-6 |
Product Name | 4-Nitrophenyl 3,4-O-isopropylidene-a-D-galactopyranoside |
IUPAC Name | (3aS,4R,6R,7R,7aR)-4-(hydroxymethyl)-2,2-dimethyl-6-(4-nitrophenoxy)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol |
Molecular Formula | C15H19NO8 |
Molecular Weight | 341.31 g/mol |
InChI | InChI=1S/C15H19NO8/c1-15(2)23-12-10(7-17)22-14(11(18)13(12)24-15)21-9-5-3-8(4-6-9)16(19)20/h3-6,10-14,17-18H,7H2,1-2H3/t10-,11-,12+,13-,14+/m1/s1 |
InChI Key | FMELJKWGVVVNFM-RGDJUOJXSA-N |
SMILES | CC1(OC2C(OC(C(C2O1)O)OC3=CC=C(C=C3)[N+](=O)[O-])CO)C |
Synonyms | 4-Nitrophenyl 3,4-O-(1-Methylethylidene)-α-D-galactopyranoside |
Canonical SMILES | CC1(OC2C(OC(C(C2O1)O)OC3=CC=C(C=C3)[N+](=O)[O-])CO)C |
Isomeric SMILES | CC1(O[C@H]2[C@H](O[C@@H]([C@@H]([C@H]2O1)O)OC3=CC=C(C=C3)[N+](=O)[O-])CO)C |
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