56193-44-3

Usage

Uses

Used in Biochemical Research:
o-NPG is used as a substrate for β-glucosidase, allowing researchers to study enzyme kinetics and perform inhibitor screening. Its hydrolysis by β-glucosidase results in the release of a yellow-colored product, o-nitrophenol, which can be quantified spectrophotometrically at 405 nm, making it a valuable tool for high-throughput assays.
Used in Molecular Biology Research:
o-NPG also serves as a model substrate for investigating the degradation of cellulose and hemicellulose in plant cell walls. This application highlights its versatility and importance in understanding the biochemical processes within plant biology.

Upstream product

• 35023-96-2 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 31208-93-2 o-nitrophenyl α-D-maltosid 
• 3053-17-6 (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 572-10-1 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl chloride 
• 25878-60-8 D-galactose pentaacetate 
• 24624-80-4 (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 88-75-5 2-hydroxynitrobenzene 

Downstream Products

• 21495-33-0 O¹-(2-nitro-phenyl)-β-D-galactopyranuronic acid 
• 144683-70-5 p-nitrophenyl O-β-D-galactopyranosyl-(1->4)-β-D-xylopyranoside 
• 100-02-7 4-nitro-phenol 
• 139639-82-0 o-nitrophenyl β-D-galactopyranosyl<1->3>-β-D-galactopyranoside 
• 139639-81-9 o-nitrophenyl β-D-galactopyranosyl<1->6>-β-D-galactopyranoside 
• 10257-28-0 D-Galactose 
• 88-75-5 2-hydroxynitrobenzene 
• 7296-64-2 β-D-galactopyranoside 
• 172982-34-2 (+)-(3,5/4,6)-3,6-diazido-4-O-(β-D-galactopyranosyl)-5-hydroxycyclohexene 
• 2595-07-5 allyl β-D-galactopyranoside 
• 3757-90-2 2-Acetamido-2-deoxy-6-O-(β-D-galactopyranosyl)-D-glucose 
• 4307-58-8 N-acetyl-D-lactosamine 
• 84049-77-4 methyl β-D-galactopyranosyl-<1->3>-α-D-glucopyranoside 
• 7115-19-7 methyl β-D-galactopyranosyl-<1->3>-β-D-galactopyranoside 

Relevant academic research and scientific papers

Aryl O- and S-galactosides and lactosides as specific inhibitors of human galectins-1 and -3: Role of electrostatic potential at O-3

Phase transfer catalyzed reaction was used for the high yielding synthesis of aryl 1-thio-β-d-galacto- and lacto-pyranosides carrying a panel of substituents on the phenyl groups. Best galectin-1 inhibitors were simple p-nitrophenyl thiogalactoside 5a for

Stereoselective Thioglycoside Syntheses. Part 6. Aryl 4-Thiomaltooligosacchrides as Chromogenic Substrates for Kinetic Studies with α-Amylase

Nucleophilic bimolecular substitution, of either o- or p-nitrophenyl 2,3,6-tri-O-benzoyl-4-O-trifluoromethylsulphonyl-α-D-galactopyranoside (1) or (2) with the sodium salt of 1-thio-α-D-glucopyranose in hexamethylphosphoramide afforded, after the usual deprotection sequences, o- and p-nitrophenyl 4-thio-α-maltosides (7) and (8).A similar synthetic scheme with (1) and the 1-α-thiolate of 4-thiomaltose (12) led to o-nitrophenyl 4,4'-dithio-α-maltotrioside (15).These 4-thio-oligosaccharides and their corresponding oxygen analogues were used, in comparative assays, as chromogenic substrates with porcine and human pancreatic α-amylases.In both series, enzymic velocity was higher for the maltotrioside derivatives than for the maltodisaccharides. o-Nitrophenyl glycosides behave as better substrates than the corresponding para isomers.Replacement of intersaccharide oxygen atoms by sulphur increased slightly the Michaelis constant, but had a negative effect on the hydrolysis rate.As a consequence, 4-thiomaltosyloligosaccharides were less sensitive substrates for pig pancreatic α-amylase as compared with their O-glycosyl counterparts.However, as the former class of compounds is split exclusively at the chromogenic site, they appear to be substrates of interest for direct kinetic studies with α-amylases.

STEREOSELECTIVE SYNTHESES OF O- AND S-NITROPHENYL GLYCOSIDES. PART III. SYNTHESES IN THE &α-D-GALACTOPYRANOSE AND &α-MALTOSE SERIES

The action of p-nitrophenol penta-O-acetyl-β-D-galactopyranose in dichloromethane, in the presence of stannic tetrachloride gave p-nitrophenyl α-D-galactoside in fair yield.This technique failed when o-nitrophenol was used.Tetra-O-acetyl-β-D-galactopyranosyl and hepta-O-acetyl-β-maltosyl chlorides were converted to p- or o-nitrophenyl α-D-glycosides and p-nitrophenyl α-D-1-thioglycosides in good yield using hexamethylphosphoramide as a solvent and the sodium salt of the phenols as nucleophiles.The galactosides have been functionalized for further condensation at the C-4 position by selective benzoylation.

Alpha-galactosidase production

A process for the production of α-galactosidase by culturing the mold Penicillium duponti in an aqueous medium containing at least one sugar with at least one αD-galactopyranosyl bond and collecting the mycelium thus obtained.