CNP-α-L-Fuc

CNP-α-L-Fuc (2-Chloro-4-nitrophenyl-α-L-fucopyranoside, CAS 157843-41-9) is a chromogenic substrate specifically designed for quantitative spectrophotometric assay of α-L-fucosidase (AFU, EC 3.2.1.51) activity, where enzymatic hydrolysis releases 2-chloro-4-nitrophenolate (2-Cl-4-NP) chromophore exhibiting intense yellow absorbance at 405 nm (ε=12,400 M⁻¹cm⁻¹) for precise kinetic measurement in clinical diagnostics and research applications. With molecular formula C12H14ClNO7 (MW 319.70 g/mol), this white crystalline solid features α-L-fucopyranose (6-deoxy-L-galactose) linked via α1-O-glycosidic bond to the electron-deficient 2-chloro-4-nitrophenyl aglycone, where ortho-chloro and para-nitro groups enhance leaving group acidity (pKa ~7.0) and hydrolysis rates (kcat/Km ~10³-10⁴ M⁻¹s⁻¹ for human lysosomal AFU and bacterial Fusobacterium α-fucosidases), ensuring >500-fold selectivity over β-fucosidases. Widely utilized in fucosidosis diagnostics (FUCA1 deficiency), cancer biomarker screening (elevated plasma AFU in malignancies), and glycobiology for profiling GH29 family fucosidases in microbiome HMO degradation, it supports one-step 96-well assays (0.5-2 mM substrate, pH 4.5-5.0, 37°C) with linear detection from 0.01-10 U/L, outperforming p-nitrophenyl-α-L-Fuc by faster turnover and reduced endogenous interference. The released chromophore’s stability across pH 6-10 enables ratiometric endpoint reads, positioning CNP-α-L-Fuc as gold standard for therapeutic monitoring, enzyme replacement therapy efficacy, and HTS of fucosidase inhibitors targeting inflammation, infection, and Lewis antigen metabolism disorders.

Appearance

• White crystalline powder.
• Hydrolysis produces yellow solution (A₄₀₅).

Source

• Koenigs-Knorr synthesis: α-L-fucopyranosyl halide + 2-chloro-4-nitrophenol.
• Commercial analytical grade (Biosynth, Chemsynlab >98%).

Molecular Weight and Structure

• Formula: C₁₂H₁₄ClNO₇; MW: 319.70 g/mol.
• (2S,3S,4R,5S,6S)-2-(2-chloro-4-nitrophenoxy)-6-methyloxane-3,4,5-triol.

Sugar Specificity

• Selective α-L-fucopyranoside for α-L-fucosidases (GH29).
• Negligible β-fucosidase activity.

Biological Activity

• Chromogenic AFU substrate; 1 U = 1 μmol CNP/min at 37°C.
• Kinetic assay at 405 nm.

Purity and Microbial Contamination

• ≥98% (HPLC, IR, NMR); heavy metals <20 ppm.
• Synthetic; non-sterile.

Identity and Quality Control

• [α]D -172.5°; mp 155-158°C; TLC single spot.
• MS/NMR verified; residue on ignition <0.5%.

Shelf Life and Storage

• Stable >2 years -20°C desiccated; DMF soluble.
• Avoid moisture/light.

Applications

• Fucosidosis diagnostics; cancer AFU biomarker.
• Glycobiology enzyme assays, HMO research.

Key Characteristics

• High specificity; sensitive 405 nm detection.
• Superior to pNP-α-L-Fuc kinetics.

Citation Links

• http://chemsynlab.com/en/product/157843-41-9.html
• https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1239784.htm
• https://www.biosynth.com (CNPF brochure)
• https://pubchem.ncbi.nlm.nih.gov/compound/11359093
• https://cymitquimica.com/cas/157843-41-9/
• https://www.echemi.com/produce/pr22061196530-2-chloro-4-nitrophenyl-alpha-l-fucopyranoside.html
• https://www.jkchemical.com/product/1527560
• https://www.smolecule.com/products/s638919
• https://senfeida.lookchem.com/products/CasNo-157843-41-9-2-Chloro-4-nitrophenyl-alpha-L-fucopyranoside-31708098.html
• http://www.chemsynlab.com/cn/product/157843-41-9.html