2818-58-8 ,苯基-b-D-半乳糖苷,
Phenyl b-D-galactopyranoside,
CAS:2818-58-8
C12H16O6 / 256.25
MFCD00063258
Phenyl b-D-galactopyranoside is a glycoside of galactose. It is used as an antigen and cross-linking agent in the preparation of monoclonal antibodies to human serum proteins. Phenyl b-D-galactopyranoside has been shown to be a potent inhibitor of protein synthesis in cells from primary tumors, and it has been found to decrease the rate of tumor growth in mice. This compound also inhibits the growth of certain bacteria, including methicillin-resistant Staphylococcus aureus (MRSA), Mycobacterium tuberculosis, and Mycobacterium avium complex. The mechanism by which phenyl b-D-galactopyranoside inhibits bacterial growth is not well understood.
Phenyl beta-D-galactopyranoside (PBG) is a chemical compound that has gained significance in scientific research in recent years. PBG is a sugar derivative that possesses a phenyl group attached to the C1 position of the pyranose ring of galactopyranoside. PBG is a white crystalline powder with a molecular weight of 294.3 g/mol. In this paper, we will discuss the definition, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity, safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions of PBG.
Definition and Background
PBG is a compound that has been extensively studied in the field of microbiology due to its ability to act as an inducer of the lac operon in Escherichia coli. The lac operon is a set of genes that are responsible for the metabolism of lactose in E. coli. PBG mimics the structure of lactose and binds to the lac repressor protein, which results in the activation of the lac operon. This allows E. coli to efficiently metabolize lactose as a source of carbon and energy.
Physical and Chemical Properties
PBG is a white crystalline powder with a melting point of 130-132°C. It is soluble in water, ethanol, and methanol. The molecular formula of PBG is C12H18O7 and its molecular weight is 294.3 g/mol.
Synthesis and Characterization
PBG can be synthesized by the reaction of phenol with galactose under acidic conditions. The resulting product is then purified using column chromatography.
The structure of PBG can be characterized using techniques such as nuclear magnetic resonance spectroscopy (NMR) and mass spectrometry (MS). The NMR spectrum of PBG shows signals corresponding to the protons on the phenyl group and the anomeric carbon of the galactopyranoside. The MS spectrum of PBG shows a molecular ion peak at m/z 294, which corresponds to the molecular weight of PBG.
Analytical Methods
PBG can be analyzed using techniques such as high-performance liquid chromatography (HPLC) and capillary electrophoresis (CE). These techniques allow for the detection and quantification of PBG in various samples.
Biological Properties
PBG has been shown to possess antimicrobial properties against a range of bacterial and fungal strains. Studies have also shown that PBG can enhance the growth of certain microorganisms such as Lactobacillus acidophilus.
Toxicity and Safety in Scientific Experiments
Studies have shown that PBG is non-toxic at concentrations typically used in scientific experiments. However, it is important to exercise caution when handling PBG and follow proper safety protocols.
Applications in Scientific Experiments
PBG is commonly used as an inducer of the lac operon in E. coli. This allows researchers to control the expression of genes of interest in E. coli. PBG can also be used as a substrate in enzymatic assays.
Current State of Research
Research on PBG is ongoing and its applications in various fields such as microbiology, enzymology, and biotechnology are being explored. Studies have also investigated the potential use of PBG as a drug delivery vehicle due to its ability to be taken up by cells.
Potential Implications in Various Fields of Research and Industry
PBG has potential implications in various fields of research and industry such as biotechnology, pharmaceuticals, and food science. PBG can be used as an inducer of gene expression in recombinant protein production. It can also be used as a substrate in enzymatic assays for drug discovery. In the food industry, PBG can be used as a flavor enhancer due to its ability to mimic the sweetness of lactose.
Limitations and Future Directions
One of the limitations of PBG is its low solubility in organic solvents. This can limit its use in certain applications. Future research can focus on developing methods to improve the solubility of PBG. Additionally, PBG's potential as a drug delivery vehicle and its antibacterial properties can be further explored.
Conclusion
PBG is a sugar derivative that has gained significance in scientific research due to its ability to act as an inducer of the lac operon in E. coli. PBG possesses antimicrobial properties, and its potential implications in various fields such as biotechnology, pharmaceuticals, and food science are being explored. Future research can focus on developing methods to improve the solubility of PBG and exploring its potential as a drug delivery vehicle.
CAS Number | 2818-58-8 |
Product Name | Phenyl beta-D-galactopyranoside |
IUPAC Name | (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-phenoxyoxane-3,4,5-triol |
Molecular Formula | C12H16O6 |
Molecular Weight | 256.25 g/mol |
InChI | InChI=1S/C12H16O6/c13-6-8-9(14)10(15)11(16)12(18-8)17-7-4-2-1-3-5-7/h1-5,8-16H,6H2/t8-,9+,10+,11-,12-/m1/s1 |
InChI Key | NEZJDVYDSZTRFS-YBXAARCKSA-N |
SMILES | C1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O |
Synonyms | phenyl-beta-D-galactopyranoside, phenyl-beta-galactoside, phenyl-D-galactopyranoside, phenyl-D-galactopyranoside, (alpha-D)-isomer, phenyl-D-galactopyranoside, (beta-D)-isomer |
Canonical SMILES | C1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O |
Isomeric SMILES | C1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O |
CAS No: 2818-58-8 MDL No: MFCD00063258 Chemical Formula: C12H16O6 Molecular Weight: 256.25 |
References: 1. Wang L, Li YM, Yip C, Qiu L, Zhou Z, Chan ASC, Adv. Synth. Catal. 2004, Vol346, Issue 8, p947-953 |
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