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501427-92-5 , Neu5Aca(2-3)Galb(1-4)GlcNAc-b-pNP; 4-Nitrophenyl O-(N-acetyl-a-neuraminosyl)-(2-3)-b-D-galactopyranosyl-(1-4)-2-acetamido-2-deoxy-b-D-glucopyranoside

501427-92-5 , Neu5Aca(2-3)Galb(1-4)GlcNAc-b-pNP;
4-Nitrophenyl O-(N-acetyl-a-neuraminosyl)-(2-3)-b-D-galactopyranosyl-(1-4)-2-acetamido-2-deoxy-b-D-glucopyranoside
Cas:501427-92-5
C31H45N3O21 / 795.70

Neu5Aca(2-3)Galb(1-4)GlcNAc-b-pNP

4-Nitrophenyl O-(N-acetyl-a-neuraminosyl)-(2-3)-b-D-galactopyranosyl-(1-4)-2-acetamido-2-deoxy-b-D-glucopyranoside

4-Nitrophenyl O-(N-acetyl-a-neuraminosyl)-(2-3)-b-D-galactopyranosyl-(1-4)-2-acetamido-2-deoxybDglucopyranoside is a fluorescent compound that has been used as a substrate in enzyme assays. It has been shown to be an effective ligand for the enzyme beta galactosidase, which hydrolyzes the substrate to produce 4nitrophenol and o-(Nacetyl)a-neuraminic acid.

Neu5Ac alpha(2-3)Gal beta(1-4)GlcNAc-beta-pNP, also known as sialyl Lewis X (sLeX) is a tetrasaccharide molecule involved in a wide range of biological processes. This molecule has attracted attention from scientists due to its unique structure and potential applications in various fields. This paper aims to provide a comprehensive overview of this molecule, including its definition and background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and 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.

Definition and Background

Neu5Ac alpha(2-3)Gal beta(1-4)GlcNAc-beta-pNP, also known as Neu5Ac alpha(2-3)Gal beta(1-4)GlcNAc-beta-pNP Lewis X (sLeX), is a tetrasaccharide molecule consisting of sialic acid (Neu5Ac), galactose (Gal), N-acetylglucosamine (GlcNAc), and para-nitrophenol (pNP). This molecule plays an important role in many biological processes, including cell adhesion, inflammation, and tissue homing. sLeX is also involved in various pathological processes such as cancer metastasis, inflammation, and microbial infections.

Physical and Chemical Properties

The chemical structure of sLeX is unique and complex. It is a tetrasaccharide comprising of the monosaccharide residues in the following order: Neu5Ac, Gal, GlcNAc, and pNP. The molecular weight of sLeX is approximately 760 Da. The melting point of sLeX is not yet determined due to its complex and dynamic structure. The solubility of sLeX varies with the solvent used; it is soluble in glycerol, ethanol, and water but insoluble in hexane and chloroform. The pH range for optimal stability of sLeX is between 4.5 and 6.5.

Synthesis and Characterization

Several methods have been used to synthesize sLeX. The most common method involves chemical synthesis using enzymatic reactions. This method involves the use of specific enzymes such as alpha-2,3-Neu5Ac alpha(2-3)Gal beta(1-4)GlcNAc-beta-pNPtransferase, beta-1,4-galactosyltransferase, and beta-1,4-N-acetylglucosaminyltransferase. The characterization of sLeX is done using various analytical techniques, including nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, high-performance liquid chromatography (HPLC), and capillary electrophoresis.

Analytical Methods

NMR spectroscopy is the most common technique used for the structural characterization of sLeX. Mass spectrometry is used to detect the molecular weight and mass distribution of sLeX. HPLC is used to separate and quantify sLeX from other molecules in a sample. Capillary electrophoresis is also used to separate and identify sLeX and other biomolecules in a sample.

Biological Properties

sLeX is involved in various biological processes, including cell adhesion, inflammation, and tissue homing. It functions by binding to specific receptors such as selectins and integrins. sLeX is also involved in various pathological processes, such as cancer metastasis, inflammation, and microbial infections.

Toxicity and Safety in Scientific Experiments

Studies on the toxicity and safety of sLeX have shown that it is relatively safe in scientific experiments. However, more research is needed to establish its acute or chronic toxicity, as well as its effects on different organs.

Applications in Scientific Experiments

sLeX has various applications in scientific experiments. Its unique structure and biological properties make it a useful tool for studying cell adhesion, inflammation, and tissue homing. It is also used in cancer research to understand the role of sLeX in cancer progression and metastasis.

Current State of Research

There is ongoing research on the various biological functions of sLeX and its potential applications in various fields. Recent studies have shown that sLeX is involved in different types of cancer, such as breast cancer, prostate cancer, and leukemia. Researchers are also exploring the potential use of sLeX in antimicrobial therapy.

Potential Implications in Various Fields of Research and Industry

The unique properties of sLeX make it a valuable molecule with potential applications in various fields. It has potential applications in drug development, cancer therapy, and as a biomarker for diseases. The use of sLeX in drug delivery could improve the targeted delivery of drugs to specific tissues or cells.

Limitations and Future Directions

Although sLeX has potential applications in various fields, there are also limitations to its use. One of the challenges in the use of sLeX is its synthesis and purification. There is a need for more efficient and cost-effective methods to synthesize and purify sLeX. Furthermore, more research is needed to establish its efficacy and safety in the treatment of different diseases. Future research should explore the use of sLeX in the development of vaccines and targeted cancer therapies.

Conclusion

Neu5Ac alpha(2-3)Gal beta(1-4)GlcNAc-beta-pNP, also known as Neu5Ac alpha(2-3)Gal beta(1-4)GlcNAc-beta-pNP Lewis X (sLeX), is a tetrasaccharide molecule with unique properties and potential applications in various fields. Its biological functions and applications have attracted the attention of researchers in different disciplines. Future research should focus on developing efficient synthesis and purification methods and exploring its potential applications in drug development and disease therapy.

CAS Number501427-92-5
Product NameNeu5Ac alpha(2-3)Gal beta(1-4)GlcNAc-beta-pNP
IUPAC Name(2S,4R,5R,6R)-5-acetamido-2-[(2S,3S,4S,5S,6S)-2-[(2S,3S,4R,5S,6S)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Molecular FormulaC31H45N3O21
Molecular Weight795.7 g/mol
InChIInChI=1S/C31H45N3O21/c1-11(38)32-19-15(40)7-31(30(46)47,54-26(19)21(42)16(41)8-35)55-27-22(43)17(9-36)51-29(24(27)45)53-25-18(10-37)52-28(20(23(25)44)33-12(2)39)50-14-5-3-13(4-6-14)34(48)49/h3-6,15-29,35-37,40-45H,7-10H2,1-2H3,(H,32,38)(H,33,39)(H,46,47)/t15-,16-,17+,18+,19-,20+,21-,22+,23-,24+,25-,26-,27+,28-,29+,31+/m1/s1
InChI KeyOUJZEVYPUZNYBL-SGZWRCNRSA-N
SMILESCC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)OC2C(C(OC(C2O)OC3C(OC(C(C3O)NC(=O)C)OC4=CC=C(C=C4)[N+](=O)[O-])CO)CO)O)O
Canonical SMILESCC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)OC2C(C(OC(C2O)OC3C(OC(C(C3O)NC(=O)C)OC4=CC=C(C=C4)[N+](=O)[O-])CO)CO)O)O
Isomeric SMILESCC(=O)N[C@@H]1[C@@H](C[C@@](O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)O)O[C@H]2[C@H]([C@@H](O[C@H]([C@H]2O)O[C@@H]3[C@@H](O[C@H]([C@H]([C@H]3O)NC(=O)C)OC4=CC=C(C=C4)[N+](=O)[O-])CO)CO)O)O


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