152957-34-1

Basic information

• Product Name: O-NITROPHENYL-N-ACETYL-BETA-D-GALACTOSAMINIDE
• Synonyms: O-NITROPHENYL-N-ACETYL-BETA-D-GALACTOSAMINIDE;2-NITROPHENYL-2-ACETAMIDO-2-DEOXY-BETA-D-GALACTOPYRANOSIDE;O-nitrophenyl-N-acetyl-B-D-*galactosaminide;2-Nitrophenyl2-acetamido-2-deoxy-b-D-galactopyranose;2-Nitrophenyl 2-acetamido-2-deoxy-β-D-galactopyranose;2-Nitrophenyl 2-(acetylamino)-2-deoxy-beta-D-galactopyranoside;(2-Nitrophenyl)-2-acetamido-2-deoxy-beta-D-galactopyranose;2-Nitrophenyl 2-acetamido-2-deoxy-b-D-galactopyranoside
• CAS NO: 152957-34-1
• Molecular Formula: C14H18N2O8
• Molecular Weight: 342.3
• EINECS: 1533716-785-6
• Product Categories: Galactosaminide;Activity;Chromogenic;ChromogenicSubstrates;Enzyme Substrates
• Mol File: 152957-34-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: −20°C
• CAS DataBase Reference: O-NITROPHENYL-N-ACETYL-BETA-D-GALACTOSAMINIDE(CAS DataBase Reference)
• NIST Chemistry Reference: O-NITROPHENYL-N-ACETYL-BETA-D-GALACTOSAMINIDE(152957-34-1)
• EPA Substance Registry System: O-NITROPHENYL-N-ACETYL-BETA-D-GALACTOSAMINIDE(152957-34-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 152957-34-1(Hazardous Substances Data)

Usage

General Description

O-Nitrophenyl-N-Acetyl-Beta-D-Galactosaminide (ONPG) is a chemical compound used as a chromogenic substrate in biological research, especially in the field of enzymology. O-NITROPHENYL-N-ACETYL-BETA-D-GALACTOSAMINIDE is specifically used in assays for detecting the presence of the enzyme beta-galactosidase, which hydrolyzes ONPG to produce o-nitrophenol, a compound that can be easily detected due to its bright yellow color. ONPG is particularly useful in the context of genetic research because it can identify bacteria that carry certain genes. It's also utilised in lactose intolerance tests, due to the enzyme's presence in the lactose digestion process. Furthermore, ONPG is a key reagent in the blue-white screening technique for recombinant DNA cloning.

Upstream product

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• 72-87-7 N-acetyl-D-mannosamine 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-mannopyrano)-[2,1:4',5']-2-oxazoline 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 3006-60-8 Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 

Relevant articles and documents

Scope of the DMC mediated glycosylation of unprotected sugars with phenols in aqueous solution

Activation of reducing sugars in aqueous solution using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and triethylamine in the presence of para-nitrophenol allows direct stereoselective conversion to the corresponding 1,2-Trans para-nitrophenyl glycosides without the need for any protecting groups. The reaction is applicable to sulfated and phosphorylated sugars, but not to ketoses or uronic acids or their derivatives. When applied to other phenols the product yield was found to depend on the pKa of the added phenol, and the process was less widely applicable to 2-Acetamido sugars. For 2-Acetamido substrates an alternative procedure in which the glycosyl oxazoline was pre-formed, the reaction mixture freeze-dried, and the crude product then reacted with an added phenol in a polar aprotic solvent system with microwave irradiation proved to be a useful simplification.

The use of the o-nitrophenyl group as a protecting/activating group for 2-acetamido-2-deoxyglucose

The o-nitrophenyl group, a protecting group with latent activation potential, was used as a protecting group for the glycosidic position. It is stable to common conditions used in synthesis and can be activated for displacement and glycoside formation by an alcohol, using zinc chloride as a catalyst. Good to excellent yields of β-glycosides of the important amino sugar N-acetylglucosamine were obtained. A mechanism for the reaction is proposed.