2-Chloro-4-nitrophenyl-alpha-L-fucopyranoside
[CAS# 157843-41-9]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyran compound
• Name: 2-Chloro-4-nitrophenyl-alpha-L-fucopyranoside
• Synonyms: (2S,3S,4R,5S,6S)-2-(2-chloro-4-nitrophenoxy)-6-methyloxane-3,4,5-triol
• Molecular Formula: C₁₇H₂₄ClNO₇
• Molecular Weight: 389.83
• CAS Registry Number: 157843-41-9
• SMILES: C[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)OC2=C(C=C(C=C2)[N+](=O)[O-])Cl)O)O)O

Properties

• Density: 1.6±0.1 g/cm³ Calc.^*
• Boiling point: 527.3±50.0 ºC 760 mmHg (Calc.)^*
• Flash point: 272.7±30.1 ºC (Calc.)^*
• Solubility: wate 100 mg/mL (Expl.)
• Index of refraction: 1.631 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Discovory and Applicatios

2-Chloro-4-nitrophenyl-alpha-L-fucopyranoside is a synthetic chromogenic substrate widely used in enzymatic assays to detect and measure the activity of alpha-L-fucosidase enzymes. The molecule consists of an alpha-L-fucopyranoside sugar moiety linked glycosidically to a 2-chloro-4-nitrophenyl group. This linkage allows alpha-L-fucosidase enzymes to hydrolyze the glycosidic bond, releasing the chromogenic 2-chloro-4-nitrophenol group.

The discovery of this compound is rooted in the development of sensitive substrates for glycosidase enzymes. The 2-chloro-4-nitrophenyl group serves as a chromophore that absorbs light strongly in the visible spectrum upon release, enabling easy quantification of enzyme activity through spectrophotometric methods. The incorporation of chlorine and nitro groups into the phenyl ring enhances the chromogenic properties by increasing the molar absorptivity and shifting the absorption to a visible wavelength.

Applications of 2-chloro-4-nitrophenyl-alpha-L-fucopyranoside primarily involve its use in biochemical and clinical laboratories to assay alpha-L-fucosidase activity. Alpha-L-fucosidase is an important lysosomal enzyme involved in the breakdown of fucose-containing glycoproteins and glycolipids. Deficiencies or abnormalities in alpha-L-fucosidase activity are associated with certain lysosomal storage disorders, such as fucosidosis, making the substrate valuable in diagnostic testing.

In research, this substrate aids in characterizing the enzymatic properties of alpha-L-fucosidase from various biological sources. It allows for the screening of potential enzyme inhibitors or modulators, which could have therapeutic relevance in diseases linked to aberrant fucosidase activity.

Additionally, 2-chloro-4-nitrophenyl-alpha-L-fucopyranoside is utilized in enzymology to study substrate specificity and enzyme kinetics, contributing to a better understanding of the enzyme’s catalytic mechanism and function.

In summary, 2-chloro-4-nitrophenyl-alpha-L-fucopyranoside is a chromogenic substrate designed for sensitive detection of alpha-L-fucosidase activity. Its role in diagnostic assays, enzymatic research, and potential therapeutic exploration highlights its significance in the biochemical field.

References

2003. Synthesis of 2-chloro-4-nitrophenyl alpha-L-fucopyranoside: a substrate for alpha-L-fucosidase (AFU). Carbohydrate Research, 338(16).
DOI: 10.1016/s0008-6215(03)00244-1

2004. Rapid kinetic rate assay of the serum alpha-L-fucosidase in patients with hepatocellular carcinoma by using a novel substrate. Clinica Chimica Acta, 347(1-2).
DOI: 10.1016/j.cccn.2004.04.007

2009. Protective Effects of Garlic and Silymarin on NDEA-Induced Rats Hepatotoxicity. International Journal of Biological Sciences, 5(6).
DOI: 10.7150/ijbs.5.549