34395-01-2 , 1,6-Anhydro-b-lactose;
Lactosan,
1,6-Anhydro-4-O-b-D-galactopyranosyl-b-D-glucopyranose,
Cas:34395-01-2
C12H20O10 / 324.28
1,6-Anhydro-4-O-b-D-galactopyranosyl-b-D-glucopyranose
N-acetyllactosamine is a monosaccharide that belongs to the group of n-acetyllactosamine. It can be found in the form of an agglutinin, lactose, and lectin. The conformation of this molecule is an equilibrium between its alpha and beta forms. The pyridine can act as an acid catalyst for the alpha conformation. There are two forms of this molecule: one synthesized from D-glucose and one synthesized from D-galactose. 1,6-Anhydro-4-O-b-D-galactopyranosyl-b-D-glucopyranose is synthesized from D-glucose. Oligosaccharides containing this molecule have been expressed in Saccharomyces cerevisiae cells and purified by affinity chromatography on columns that contain immobilized antibody to human serum albumin.
1,6-Anhydrolactose (1,6-ANL) is a lactose derivative that has been gaining attention in recent years for its potential applications in various fields, including biomedicine, food technology, and material science. It is a cyclic compound that is formed when a lactose molecule loses a water molecule from the hydroxyl group at the sixth position. This reaction can occur spontaneously, but it can also be induced by different methods, such as acid hydrolysis, heat treatment, or enzymatic conversion.
Synthesis and Characterization
As mentioned, 1,6-ANL can be synthesized by different methods, depending on the desired purity and yield. Acid-catalyzed hydrolysis of lactose is one of the most common methods used to produce 1,6-ANL, but it can also result in the formation of other by-products such as lactulose, galactose, and glucose. Enzymatic conversion using β-galactosidase has been shown to be a more selective and efficient method for 1,6-ANL synthesis, but it requires specific conditions such as pH, temperature, and substrate concentration.
Characterization of 1,6-ANL is essential to determine its purity, structure, and properties. Techniques such as Nuclear Magnetic Resonance (NMR), Infrared (IR) spectroscopy, and High-Performance Liquid Chromatography (HPLC) can be used to identify 1,6-ANL and quantify its content in a sample. Crystallography and X-ray diffraction can also provide information about its crystal structure and morphology.
Analytical Methods
Detection and quantification of 1,6-ANL in complex matrices, such as food products, require sensitive and specific analytical methods. Currently, several methods have been developed for the determination of 1,6-ANL, including liquid chromatography-mass spectrometry (LC-MS), gas chromatography-mass spectrometry (GC-MS), and capillary electrophoresis (CE). However, the lack of standardization and reference materials limits the comparability and reliability of these methods.
Biological Properties
Several studies have investigated the biological properties of 1,6-ANL, including its antioxidant, anti-inflammatory, and prebiotic effects. As a prebiotic, 1,6-ANL has been shown to selectively stimulate the growth of beneficial gut bacteria, such as Bifidobacteria and Lactobacilli, and increase the production of short-chain fatty acids (SCFAs). Moreover, 1,6-ANL has been demonstrated to have immunomodulatory effects on both innate and adaptive immune responses, suggesting its potential as a novel therapeutic agent for immune-mediated disorders.
Toxicity and Safety in Scientific Experiments
Toxicity and safety evaluation are critical steps in the development of any new chemical compound, including 1,6-ANL. Several studies have investigated the acute and subchronic toxicity of 1,6-ANL in different animal models, and the results indicate that it is relatively safe at doses ranging from 100 to 5000 mg/kg. However, further studies are needed to investigate the potential long-term effects of 1,6-ANL consumption on human health and determine its maximum tolerated dose (MTD).
Applications in Scientific Experiments
1,6-ANL has potential applications in various scientific fields, including biomedicine, food technology, and material science. In biomedicine, 1,6-ANL can be used as a dietary supplement, a prebiotic, and an immunomodulatory agent. In food technology, it can be used as a functional ingredient to improve the nutritional and sensory properties of food products. In material science, it can be used as a building block for the synthesis of new macromolecules or as a template for the formation of metal nanoparticles.
Current State of Research
Despite growing attention in recent years, the research on 1,6-ANL is still relatively limited, and several gaps need to be addressed. The lack of standardization and reference materials for analytical methods hinders the comparability and reliability of the published data. Moreover, there is a need for more in-depth studies to investigate the potential applications of 1,6-ANL in different scientific fields, understand its mechanism of action, and determine its toxicity and safety in different contexts.
Potential Implications in Various Fields of Research and Industry
1,6-ANL has several potential implications in different scientific fields and industries, including:
- Biomedical science: 1,6-ANL has potential applications as a dietary supplement, a prebiotic, and an immunomodulatory agent. It can be used to improve gut health, prevent and treat immune-mediated disorders, and enhance overall health and well-being.
- Food technology: 1,6-ANL can be used as a functional ingredient to improve the nutritional and sensory properties of food products. It can be used to replace sucrose or other sweeteners, reduce fat content, and enhance the dietary fiber content of food products.
- Material science: 1,6-ANL can be used as a building block for the synthesis of new macromolecules or as a template for the formation of metal nanoparticles. It can be used to design new materials with unique properties such as biocompatibility, self-assembly, and biodegradability.
Limitations and Future Directions
There are several limitations and challenges that need to be addressed to enhance the potential applications of 1,6-ANL in different fields, including:
- Standardization and reference materials for analytical methods: The lack of standardization and reference materials for analytical methods limits the comparability and reliability of the published data. The development of reference materials and standard methods is essential to advance the research on 1,6-ANL.
- Toxicity and safety evaluation: Further studies are needed to investigate the long-term effects of 1,6-ANL consumption on human health and determine its maximum tolerated dose (MTD).
- Mechanism of action: The mechanism of action of 1,6-ANL in different contexts is not fully understood, and more studies are needed to elucidate its mechanism of action and its interactions with other compounds.
- Potential applications in new fields: The potential applications of 1,6-ANL in new fields, such as energy storage, drug delivery, and environmental remediation, need to be explored, and the feasibility of these applications needs to be evaluated.
- Optimization of synthesis and characterization methods: The optimization of synthesis and characterization methods is essential to improve the purity and yield of 1,6-ANL and reduce the formation of unwanted by-products.
In conclusion, 1,6-ANL is a promising lactose derivative that has potential applications in various scientific fields and industries. Its unique properties, such as prebiotic effects, immunomodulatory effects, and structural versatility, make it an attractive candidate for the development of new materials, food products, and therapeutic agents. However, more studies are needed to address the limitations and challenges that hinder the advancement of the research on 1,6-ANL and unlock its full potential.
CAS Number | 34395-01-2 |
Product Name | 1,6-Anhydrolactose |
IUPAC Name | (2S,3R,4S,5R,6R)-2-[[(1S,2S,3R,4R,5S)-3,4-dihydroxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol |
Molecular Formula | C12H20O10 |
Molecular Weight | 324.28 g/mol |
InChI | InChI=1S/C12H20O10/c13-1-3-5(14)6(15)8(17)12(20-3)22-10-4-2-19-11(21-4)9(18)7(10)16/h3-18H,1-2H2/t3-,4+,5+,6+,7-,8-,9-,10-,11+,12+/m1/s1 |
InChI Key | LTYZUJSCZCPGHH-BNQXPIRTSA-N |
SMILES | C1C2C(C(C(C(O1)O2)O)O)OC3C(C(C(C(O3)CO)O)O)O |
Synonyms | 1,6-anhydrolactose |
Canonical SMILES | C1C2C(C(C(C(O1)O2)O)O)OC3C(C(C(C(O3)CO)O)O)O |
Isomeric SMILES | C1[C@H]2[C@H]([C@@H]([C@H]([C@@H](O1)O2)O)O)O[C@H]3[C@@H]([C@H]([C@H]([C@H](O3)CO)O)O)O |
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