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13000-25-4 , Lactosamine , 4-O-(b-D-Galactopyranosyl)-D-glucosamine

13000-25-4 , Lactosamine ,
4-O-(b-D-Galactopyranosyl)-D-glucosamine
C12H23NO10 / 341.31
MFCD01310604

Lactosamine , 4-O-(b-D-Galactopyranosyl)-D-glucosamine

4-O-(b-D-Galactopyranosyl)-D-glucosamine is a sugar that is found in the human body. It has been shown to have anti-cancer properties and is being studied as a potential therapeutic agent for squamous cell carcinoma. Basic structural analysis of 4-O-(b-D-Galactopyranosyl)-D-glucosamine has been performed on methyl glycosides, oligosaccharides, and bovine serum albumin. The sugar can be used to inhibit transcriptional regulation through its interactions with DNA. 4-O-(b-D-Galactopyranosyl)-D-glucosamine has also been found to inhibit the activities of enzymes involved in methyl glycoside synthesis, which may be related to its effects on cancer cells.

Polylactosamine, a polymer composed of β-linked N-acetyllactosamine units, is an important constituent of the extracellular matrix and cell surface glycoconjugates. Polylactosamine is involved in various cellular functions, including cell adhesion, migration, proliferation, and signaling. The unique physical and chemical properties of polylactosamine make it an attractive material for a wide range of applications in scientific research and industry.

Definition and Background:

Polylactosamine is a high-molecular-weight polymer composed of β-linked N-acetyllactosamine units. These units are linked together by a β-1, 3-glycosidic bond, resulting in a linear polymer chain. Polylactosamine is also known as poly-LacNAc or poly-N-acetyllactosamine.

Polylactosamine is found in various tissues, including the extracellular matrix, cell surface glycoconjugates, and secreted glycoproteins. The structure of polylactosamine varies depending on the tissue and developmental stage. In humans, polylactosamine is found in various tissues, including the nervous system, liver, kidney, and lung.

Physical and Chemical Properties:

Polylactosamine is a complex polymer that exhibits unique physical and chemical properties. The polymer chain is linear and may contain up to several hundred N-acetyllactosamine units. Polylactosamine is hydrophilic and can interact with water through hydrogen bonding. The physical properties of polylactosamine are influenced by its degree of polymerization, molecular weight distribution, and conformational flexibility.

The chemical properties of polylactosamine are determined by its chemical structure. Polylactosamine contains numerous hydroxyl and amine groups, which can participate in various chemical reactions, including oxidation, reduction, and esterification. The electrophilic properties of the N-acetyllactosamine units can be used for covalent modification and conjugation with other molecules.

Synthesis and Characterization:

Polylactosamine can be synthesized by enzymatic and chemical methods. The enzymatic synthesis of polylactosamine involves the use of glycosyltransferases, which catalyze the transfer of N-acetyllactosamine units from donor substrates to acceptor substrates. Chemical synthesis of polylactosamine involves the coupling of N-acetyllactosamine monomers using coupling agents, such as dicyclohexylcarbodiimide (DCC), to form a polymer chain.

The characterization of polylactosamine requires various analytical methods, including gel permeation chromatography (GPC), nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry. These techniques provide information on the molecular weight distribution, degree of polymerization, and structural features of polylactosamine.

Analytical Methods:

Analytical methods are necessary for the analysis of polylactosamine in biological samples and synthetic products. The detection and quantification of polylactosamine can be achieved using various analytical techniques, including enzymatic assays, lectin binding, fluorescence labeling, and chromatography.

Enzymatic assays involve the use of enzymes that specifically recognize polylactosamine, such as β1, 4-galactosyltransferase and sialyltransferase. Lectin binding assays use lectins, which bind to specific carbohydrate epitopes of polylactosamine. Fluorescence labeling involves the conjugation of fluorescent dyes to polylactosamine for visual detection. Chromatography includes ion exchange chromatography, gel permeation chromatography, and reverse-phase chromatography.

Biological Properties:

Polylactosamine plays a crucial role in various biological processes, including cell adhesion, migration, proliferation, and signaling. Polylactosamine is involved in the regulation of cell surface receptor activities, such as integrins, growth factor receptors, and immunoglobulin superfamily members. Polylactosamine also modulates signal transduction pathways, such as the Wnt and Notch pathways.

The biological activities of polylactosamine are mediated by its interactions with various proteins and enzymes. Polylactosamine interacts with lectins, such as galectins, which regulate cell adhesion and apoptosis. Polylactosamine also interacts with proteoglycans, such as heparan sulfate proteoglycans, which modulate growth factor signaling.

Toxicity and Safety in Scientific Experiments:

The toxicity and safety of polylactosamine are important considerations in scientific experiments that involve the use of polylactosamine-based materials. Several studies have investigated the toxicity of polylactosamine and its derivatives in different cell types and animal models.

The toxicity of polylactosamine is influenced by its physical and chemical properties, such as its molecular weight and degree of acetylation. Polylactosamine can induce cytotoxicity, apoptosis, and inflammatory responses when administered at high concentrations. However, polylactosamine-based materials have been shown to be safe when used in appropriate concentrations and formulations.

Applications in Scientific Experiments:

Polylactosamine has various applications in scientific research, including the development of biomaterials, drug delivery systems, and therapeutics. Polylactosamine-based materials can be used for the immobilization of cells and enzymes, the delivery of drugs and genes, and the modulation of cell signaling pathways.

Polylactosamine-based materials can also be used for the development of biosensors, bioimaging agents, and tissue engineering scaffolds. Polylactosamine-based biosensors can detect various biomolecules, such as proteins, nucleic acids, and lipids, with high sensitivity and specificity.

Current State of Research:

The current state of research on polylactosamine is focused on the development of novel applications and the elucidation of its biological functions. Polylactosamine-based materials have shown promising results in preclinical studies for drug delivery, tissue engineering, and biosensing applications.

The biological functions of polylactosamine are still poorly understood, and the elucidation of its molecular mechanisms remains a subject of ongoing research. The identification and characterization of polylactosamine binding proteins and enzymes will provide insights into its biological activities and potential therapeutic applications.

Limitations and Future Directions:

The limitations of polylactosamine-based materials include their complex synthesis, limited availability, and variable biological activities. The development of more efficient and scalable synthesis methods and the optimization of the physicochemical properties of polylactosamine-based materials will facilitate their widespread use in scientific research.

Future directions for research on polylactosamine include the identification and characterization of polylactosamine-binding proteins and enzymes, the development of novel polylactosamine-based materials with tailored properties, and the investigation of polylactosamine's role in various physiological and pathological processes.

CAS Number13000-25-4
Product NamePolylactosamine
IUPAC Name(2R,3R,4S,5R)-2-amino-3,5,6-trihydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanal
Molecular FormulaC12H23NO10
Molecular Weight341.31 g/mol
InChIInChI=1S/C12H23NO10/c13-4(1-14)7(18)11(5(17)2-15)23-12-10(21)9(20)8(19)6(3-16)22-12/h1,4-12,15-21H,2-3,13H2/t4-,5+,6+,7+,8-,9-,10+,11+,12-/m0/s1
InChI KeyLAVNEPYDFKGEOD-JVCRWLNRSA-N
SMILESC(C1C(C(C(C(O1)OC(C(CO)O)C(C(C=O)N)O)O)O)O)O
Synonymspolylactosamine
Canonical SMILESC(C1C(C(C(C(O1)OC(C(CO)O)C(C(C=O)N)O)O)O)O)O
Isomeric SMILESC([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]([C@@H](CO)O)[C@@H]([C@H](C=O)N)O)O)O)O)O


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