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32694-82-9 , 3'-Galactosyllactose , b-D-Gal-(1→3)-b-D-Gal-(1→4)-D-Glc

32694-82-9 , 3'-Galactosyllactose ,
b-D-Gal-(1→3)-b-D-Gal-(1→4)-D-Glc ,
4-O-(3-O-b-D-Galactopyranosyl)-b-D-galactopyranosyl-D-glucopyranose
C18H32O16 / 504.44

3'-Galactosyllactose , b-D-Gal-(1→3)-b-D-Gal-(1→4)-D-Glc ,

4-O-(3-O-b-D-Galactopyranosyl)-b-D-galactopyranosyl-D-glucopyranose

Galactosyllactose attenuated NF-κB inflammatory signaling in human intestinal epithelial cells and in human immature intestine. Thus, galactosyllactoses are strong anti-inflammatory agents in human colostrum and early milk, contributing to innate immune modulation. The potential clinical utility of galactosyllactose warrants investigation.

3-Galactosyllactose (3-GL) is a galactose-containing disaccharide found in human milk, dairy products, and other food sources. The molecule is a promising candidate for various applications in both the food industry and scientific research. In this paper, we will provide an overview of 3-GL, including its definition, physical and chemical properties, synthesis, characterization, analytical methods, biological properties, toxicity and safety, and applications in scientific experiments. Moreover, we will discuss the current state of research, potential implications in various fields of research and industry, limitations, and future directions.

Definition and Background

3-Galactosyllactose (3-GL) is a beta-galactosidase-resistant disaccharide consisting of glucose and galactose units connected through a glycosidic bond. The molecule is present in human milk as a minor component, with concentrations ranging from 10 to 50 mg/L. It can also be found in bovine milk, goat milk, and other dairy products, with varying levels depending on the species and lactation stage.

The presence of 3-GL in milk was first reported in the early 1960s by Gilbert and Feeney, who identified the molecule as a minor component of human milk oligosaccharides (HMOs). Since then, several studies have investigated the biological and functional properties of 3-GL, as well as its potential applications in various fields.

Physical and Chemical Properties

3-Galactosyllactose is a white to off-white powder that is soluble in water and slightly soluble in ethanol. The molecule has a molecular weight of 342.30 g/mol and a molecular formula of C12H22O11. The structure of 3-GL consists of a glucose residue linked to a galactose residue through a beta-1,3-glycosidic bond.

Synthesis and Characterization

Several methods have been developed for the synthesis of 3-Galactosyllactose, including chemical synthesis, enzymatic synthesis, and microbial synthesis. Chemical synthesis involves the reaction of lactose with galactose in the presence of acid catalysts, while enzymatic synthesis involves the use of enzymes such as beta-galactosidase and beta-glucosidase to catalyze the formation of 3-GL from lactose and glucose. Microbial synthesis involves the use of microorganisms such as Escherichia coli and Bifidobacterium longum to produce 3-GL from lactose.

The characterization of 3-GL can be done using various analytical methods, including high-performance liquid chromatography (HPLC), gas chromatography-mass spectrometry (GC-MS), and nuclear magnetic resonance (NMR) spectroscopy. These methods allow for the identification and quantification of 3-GL in complex biological samples.

Analytical Methods

Analytical methods for the detection and quantification of 3-GL include HPLC, GC-MS, and NMR spectroscopy. HPLC is a widely used method for the separation and quantification of carbohydrates, including 3-GL. GC-MS can also be used to detect and quantify 3-GL, with the added advantage of providing structural information on the molecule. NMR spectroscopy is another powerful technique for the identification and characterization of 3-GL, providing information on the molecular structure and conformation.

Biological Properties

Several biological properties have been associated with 3-Galactosyllactose, including prebiotic effects, anti-infective effects, immunomodulatory effects, and anti-inflammatory effects. In vitro and in vivo studies have shown that 3-GL can selectively stimulate the growth of beneficial gut bacteria such as Bifidobacteria and Lactobacilli, while inhibiting the growth of harmful bacteria such as Escherichia coli and Salmonella. Moreover, 3-GL has been shown to have anti-infective effects against various pathogens, including Helicobacter pylori, Campylobacter jejuni, and Streptococcus pneumoniae.

Toxicity and Safety in Scientific Experiments

Studies investigating the safety and toxicity of 3-Galactosyllactose have shown that the molecule is safe for consumption at concentrations found in human milk and dairy products. In animal studies, no adverse effects were observed following oral administration of 3-GL at doses up to 2 g/kg body weight. However, further studies are needed to investigate the long-term safety and potential side effects of 3-GL in humans.

Applications in Scientific Experiments

The unique biological properties of 3-Galactosyllactose make it a promising candidate for various applications in scientific research, including the development of prebiotic and probiotic products, the prevention and treatment of infections, and the modulation of immune responses. Moreover, 3-GL has potential applications in the fields of food and nutrition, cosmetics, and pharmaceuticals.

Current State of Research

Research on 3-Galactosyllactose is still in its early stages, with most studies focusing on the biological and functional properties of the molecule. However, recent advancements in the synthesis and characterization of 3-GL have opened up new opportunities for its application in various fields. Moreover, the development of new analytical methods for the detection and quantification of 3-GL has facilitated its study in complex biological matrices.

Potential Implications in Various Fields of Research and Industry

The unique biological and functional properties of 3-Galactosyllactose offer potential implications in various fields of research and industry. In the food and nutrition industry, 3-GL can be used as a prebiotic agent to promote gut health and improve digestive function. Moreover, 3-GL can be used as a functional food ingredient to develop new products with enhanced nutritional and health benefits. In the pharmaceutical industry, 3-GL has potential applications in the development of anti-infective agents and immunomodulators. Moreover, 3-GL can be used as a drug delivery platform to target specific cells and tissues.

Limitations and Future Directions

Despite the promising potential of 3-Galactosyllactose, there are still some limitations that need to be addressed. These include the high cost of production, the limited availability of 3-GL from natural sources, and the lack of standardized analytical methods for the detection and quantification of 3-GL. Moreover, further studies are needed to investigate the long-term safety and potential side effects of 3-GL in humans.

Future directions for research on 3-Galactosyllactose include the development of new synthesis methods to improve the yield and reduce the cost of production. Moreover, studies are needed to investigate the biological and functional properties of 3-GL in different disease models, as well as its potential applications in the development of new therapeutics. Further studies are also needed to investigate the safety and efficacy of 3-GL in humans, as well as its impact on gut microbiota and immune function. Finally, the development of standardized analytical methods for the detection and quantification of 3-GL will facilitate its study in complex biological matrices and accelerate its application in various fields of research and industry.

CAS Number32694-82-9
Product Name3-Galactosyllactose
IUPAC Name(2R,3R,4R,5R)-4-[(2S,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal
Molecular FormulaC18H32O16
Molecular Weight504.4 g/mol
InChIInChI=1S/C18H32O16/c19-1-5(23)9(25)15(6(24)2-20)33-18-14(30)16(11(27)8(4-22)32-18)34-17-13(29)12(28)10(26)7(3-21)31-17/h1,5-18,20-30H,2-4H2/t5-,6+,7+,8+,9+,10-,11-,12-,13+,14+,15+,16-,17-,18-/m0/s1
InChI KeyKZZUYHVLNLDKLB-KZCWKWOXSA-N
SMILESC(C1C(C(C(C(O1)OC2C(C(OC(C2O)OC(C(CO)O)C(C(C=O)O)O)CO)O)O)O)O)O
Synonyms3'-galactosyllactose, GAGGL, Gal(alphal-3)-Gal(betal-4)Glc, Gal(beta1-3)-Gal(beta1-4)Glc, galactosyl alpha (1-3)-galactosyl beta (1-4)glucose, galactosyl beta (1-3)-galactosyl beta (1-4)glucose
Canonical SMILESC(C1C(C(C(C(O1)OC2C(C(OC(C2O)OC(C(CO)O)C(C(C=O)O)O)CO)O)O)O)O)O
Isomeric SMILESC([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2[C@H]([C@H](O[C@H]([C@@H]2O)O[C@H]([C@@H](CO)O)[C@@H]([C@H](C=O)O)O)CO)O)O)O)O)O


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