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  • 42891-16-7 ,N-辛基-b-D-硫代吡喃半乳糖苷, Octyl b-D-thiogalactopyranoside
42891-16-7 ,N-辛基-b-D-硫代吡喃半乳糖苷, Octyl b-D-thiogalactopyranoside

42891-16-7 ,N-辛基-b-D-硫代吡喃半乳糖苷, Octyl b-D-thiogalactopyranoside

42891-16-7 ,N-辛基-b-D-硫代吡喃半乳糖苷,
Octyl b-D-thiogalactopyranoside,
Cas:42891-16-7
C14H28O5S / 308.43
MFCD00133686

Octyl b-D-thiogalactopyranoside

N-辛基-b-D-硫代吡喃半乳糖苷,

Octyl b-D-thiogalactopyranoside is a methylated derivative of galactose. It is a polysaccharide that is used to modify saccharides and oligosaccharides for research purposes. The product is used in glycosylation reactions and can be custom synthesized to meet specific requirements. Octyl b-D-thiogalactopyranoside has been modified with fluorine, which increases its stability against hydrolysis. 

Definition and Background

N-Octyl-beta-D-thiogalactopyranoside (OTG) is a non-ionic surfactant commonly used as a solubilizing agent in membrane biochemistry and protein purification. OTG is a member of the family of alkyl-thioglucosides, and it is composed of an octyl chain and a thiogalactopyranoside headgroup (1). OTG is known for its unique properties as a mild and effective detergent, which preserves the structural integrity and activity of proteins in solution (2). OTG is also used as a substrate for detecting beta-galactosidase activity in histochemical and biochemical assays (3).

Synthesis and Characterization

The synthesis of OTG involves the reaction of 2-thiogalactose with 1-octanol under acidic conditions, followed by purification through crystallization (8). The purity and identity of OTG can be confirmed by various methods, including high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR), and mass spectrometry (MS) (9).

Analytical Methods

OTG can be quantified by various analytical methods, including HPLC, reversed-phase chromatography, and ultraviolet-visible (UV-Vis) spectroscopy (10). HPLC is the most commonly used method to determine the purity and concentration of OTG (11). The presence of OTG can also be detected by thin-layer chromatography (TLC) and colorimetric assays using o-nitrophenyl-beta-D-galactopyranoside (ONPG) as a substrate for beta-galactosidase (12).

Biological Properties

OTG has been shown to have minimal effects on the biological activities of proteins and enzymes (13). OTG is a non-denaturing detergent that preserves the native conformation and function of proteins in solution (14). OTG is commonly used in protein crystallization, as it stabilizes the crystal lattice and enhances the diffraction quality of the protein crystals (15).

Toxicity and Safety in Scientific Experiments

OTG is generally considered safe to use in scientific experiments when handled properly (16). However, OTG can be harmful if ingested or inhaled, and can cause skin and eye irritation (17). OTG should be handled in a fume hood and with appropriate personal protective equipment, including gloves and goggles.

Applications in Scientific Experiments

OTG has a wide range of applications in scientific experiments, including protein solubilization, purification, and crystallization (18). OTG is also used as a detergent in membrane protein research, as it can extract membrane proteins while maintaining their functionality (19). OTG is used as a substrate for detecting beta-galactosidase activity in biochemical and histochemical assays (20). OTG is also used as a non-ionic detergent in protein electrophoresis and immunoblotting (21).

Current State of Research

OTG is a well-established detergent in biochemistry, and its use in protein research is extensively documented in the literature (22). Recent research has focused on improving the properties of OTG, including its solubility, stability, and diffusion coefficient, to enhance its applications in protein research (23).

Potential Implications in Various Fields of Research and Industry

OTG has potential implications in various fields of research and industry, including biotechnology, pharmaceuticals, and food science. OTG can be used as a solubilizing agent for membrane proteins, which could lead to the development of new therapeutic drugs targeting membrane-bound receptors (24). OTG can also be used as a detergent in the food industry, particularly in the production of dairy products such as cheese and yogurt (25).

Limitations and Future Directions

Despite its widespread use, OTG has some limitations, including its high cost and low yield during synthesis (26). Furthermore, OTG may interfere with some analytical techniques, such as electrophoresis and enzyme assays, due to its hydrophobic properties (27). Future research should focus on developing novel OTG-related compounds that are more cost-effective and can overcome some of the limitations of OTG. Additionally, future research should investigate the potential of OTG in other fields of research, such as nanotechnology and biomedical engineering.

Conclusion

OTG is a unique surfactant that has found wide applications in protein research, particularly in protein solubilization, purification, and crystallization. OTG has minimal effects on the biological activities of proteins and is generally safe to use in scientific experiments when handled properly. OTG has potential implications in various fields of research and industry, and future research should focus on developing novel OTG-related compounds and investigating its potential in other fields of research.

CAS Number42891-16-7
Product NameN-Octyl-beta-D-thiogalactopyranoside
IUPAC Name(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-octylsulfanyloxane-3,4,5-triol
Molecular FormulaC14H28O5S
Molecular Weight308.43 g/mol
InChIInChI=1S/C14H28O5S/c1-2-3-4-5-6-7-8-20-14-13(18)12(17)11(16)10(9-15)19-14/h10-18H,2-9H2,1H3/t10-,11+,12+,13-,14+/m1/s1
InChI KeyCGVLVOOFCGWBCS-HTOAHKCRSA-N
SMILESCCCCCCCCSC1C(C(C(C(O1)CO)O)O)O
Canonical SMILESCCCCCCCCSC1C(C(C(C(O1)CO)O)O)O
Isomeric SMILESCCCCCCCCS[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O


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