22153-71-5

Basic information

• Product Name: 4-NITROPHENYL-BETA-L-FUCOPYRANOSIDE
• Synonyms: 4-nitrophenyl6-deoxy-beta-l-galactopyranosid;PNP-BETA-L-FUC;PNP BETA-L-FUCOPYRANOSIDE;P-NITROPHENYL BETA-L-FUCOPYRANOSIDE;P-NITROPHENYL-BETA-L-FUCOSIDE;NITROPHENYL-B-L-FUCOPYRANOSIDE, 4-;4-NITROPHENYL-BETA-L-FUCOPYRANOSIDE;4-NITROPHENYL-BETA-L-FUCOSIDE
• CAS NO: 22153-71-5
• Molecular Formula: C₁₂H₁₅NO₇
• Molecular Weight: 285.25
• EINECS: 244-808-3
• Product Categories: Substrates;substrate
• Mol File: 22153-71-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 515.4 °C at 760 mmHg
• Flash Point: 265.5 °C
• Appearance: /
• Density: 1.503 g/cm³
• Vapor Pressure: 1.9E-11mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: −20°C
• PKA: 12.68±0.70(Predicted)
• CAS DataBase Reference: 4-NITROPHENYL-BETA-L-FUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITROPHENYL-BETA-L-FUCOPYRANOSIDE(22153-71-5)
• EPA Substance Registry System: 4-NITROPHENYL-BETA-L-FUCOPYRANOSIDE(22153-71-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 22153-71-5(Hazardous Substances Data)

Usage

Description

4-NITROPHENYL-BETA-L-FUCOPYRANOSIDE is a beta-L-fucoside that is beta-L-fucopyranose in which the anomeric hydroxy hydrogen is replaced by a 4-nitrophenyl group. It is a white to off-white powder and serves as a chromogenic substrate for β-D-Fucosidase, producing a yellow solution upon cleavage.

Uses

Used in Enzyme Assays:
4-NITROPHENYL-BETA-L-FUCOPYRANOSIDE is used as a chromogenic substrate for β-D-Fucosidase enzyme assays. It allows for the detection and quantification of the enzyme's activity by producing a yellow solution upon cleavage.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-NITROPHENYL-BETA-L-FUCOPYRANOSIDE is used as a research tool for studying the activity and inhibition of β-D-Fucosidase enzymes. This can help in the development of drugs targeting these enzymes for various therapeutic applications.
Used in Biochemical Research:
4-NITROPHENYL-BETA-L-FUCOPYRANOSIDE is used as a biochemical research tool for investigating the structure, function, and interactions of β-D-Fucosidase enzymes. This can contribute to a better understanding of the enzyme's role in biological processes and potential applications in medicine and biotechnology.

InChI:InChI=1/C12H15NO7/c1-6-9(14)10(15)11(16)12(19-6)20-8-4-2-7(3-5-8)13(17)18/h2-6,9-12,14-16H,1H3/t6-,9+,10+,11-,12+/m0/s1

Upstream product

• 18992-37-5 4-nitrophenyl-2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranoside 
• 100-02-7 4-nitro-phenol 
• 5160-09-8 2,3,4‐tri‐O‐acetyl-α-L‐rhamnopyranosyl chloride 
• 24332-99-8 p-nitrophenyl 2,3,4-tri-O-acetyl-β-L-fucopyranoside 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 
• 73-34-7 6-deoxy-L-galactose 
• 16741-27-8 2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide 

Downstream Products

• 183878-99-1 1-(4-aminophenoxy)-α-L-rhamnopyranoside 
• 69936-58-9 p-aminophenyl-β-L-fucopyranoside 
• 88043-70-3 p-nitrophenyl 2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 183878-09-3 p-Nitrophenyl 3,4-O-isopropylidene-β-L-fucoside 
• 260051-35-2 C₂₆H₂₃NO₉ 
• 183878-18-4 p-nitrophenyl 3-O-methyl-β-L-fucopyranoside 
• 183878-52-6 p-Nitrophenyl 3-O-methoxycarbonylmethyl-β-L-fucopyranoside 
• 10427-74-4 p-Aminophenyl 3-deoxy-β-L-fucoside 
• 183878-50-4 p-Aminophenyl 4-deoxy-β-L-fucoside 
• 183878-21-9 p-aminophenyl 3-O-methyl-β-L-fucopyranoside 
• 183878-15-1 p-Aminophenyl 2-O-methyl-β-L-fucoside 
• 183878-43-5 p-nitrophenyl 3,6-dideoxy-3-chloro-β-L-guloside 
• 183878-12-8 p-nitrophenyl 2-O-methyl-3,4-O-isopropylidene-β-L-fucoside 
• 183878-41-3 p-nitrophenyl 3,6-dideoxy-3-chloro-4-O-acetyl-β-L-guloside 

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.

Glycosynthase with broad substrate specificity-an efficient biocatalyst for the construction of oligosaccharide library

A versatile glycosynthase (TnG-E338A) with strikingly broad substrate scope has been developed from Thermus nonproteolyticus β-glycosidase (TnG) by using site-directed mutagenesis. The practical utility of this biocatalyst has been demonstrated by the facile generation of a small library containing various oligosaccharides and a steroidal glycoside (total 25 compounds) in up to 100 % isolated yield. Moreover, an array of eight gluco-oligosaccharides has been readily synthesized by the enzyme in a one-pot, parallel reaction, which highlights its potential in the combinatorial construction of a carbohydrate library that will assist glycomic and glycotherapeutic research. Significantly, the enzyme provides a means by which glycosynthase technology may be extended to combinatorial chemistry.