142925-37-9

Basic information

• Product Name: 4-nitrophenyl β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
• CAS NO: 142925-37-9
• Molecular Weight: 504.448
• Mol File: 142925-37-9.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 4-nitrophenyl β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4-nitrophenyl β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside(142925-37-9)
• EPA Substance Registry System: 4-nitrophenyl β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside(142925-37-9)

Safety Data

• Hazardous Substances Data: 142925-37-9(Hazardous Substances Data)

Upstream product

• 133-89-1 uridine-5'-diphosphogalactose 
• 3459-18-5 4-nitrophenyl N-acetyl-β-D-glucosaminide 
• 73208-61-4 N-acetyllactosamine peracetate 
• 4307-58-8 N-acetyl-D-lactosamine 
• 25878-60-8 D-galactose pentaacetate 
• 439-03-2 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl fluoride 
• 2021-84-3 α-galactosyl fluoride 
• 13089-27-5 p-nitrophenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 62398-01-0 2-acetamido-3,6-di-O-acetyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranosyl chloride 
• 100-02-7 4-nitro-phenol 
• 467447-14-9 phenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-2-deoxy-6-O-(4-methoxybenzyl-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside 
• 467447-12-7 phenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-(4-methoxybenzyl-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside 
• 467448-47-1 4-nitrophenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-3-O-acetyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-β-D-glucopyranoside 

Downstream Products

• 177855-99-1 N-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-4-hydroxy-6-hydroxymethyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yl]-acetamide 
• 157383-90-9 p-Aminophenyl 2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-β-D-glucopyranoside 
• 59-23-4 D-Galactose 
• 501427-93-6 α-D-Neu5Ac-(2->6)-β-D-Gal-(1->4)-β-D-GlcNAc-OC6H4NO2-p 
• 501427-92-5 α-D-Neu5Ac-(2->3)-β-D-Gal-(1->4)-β-D-GlcNAc-OC6H4NO2-p 

Relevant articles and documents

Efficient preparation of natural and synthetic galactosides with a recombinant β-1,4-galactosyltransferase-/UDP-4′-gal epimerase fusion protein

The numerous biological roles of LacNAc-based oligosaccharides have led to an increased demand for these structures for biological studies. In this report, an efficient route for the synthesis of β-galactosides using a bacterial β-4-galactosyltransferase/-UDP-4′-gal-epimerase fusion protein is described. The lgtB gene from Neisseria meningitidis and the galE gene from Streptococcus thermophilus were fused and cloned into an expression vector pCW. The fusion protein transfers galactose to a variety of different glucose- and glucosamine-containing acceptors, and utilizes either UDP-galactose or UDP-glucose as donor substrates. A crude lysate from Escherichia coli expressing the fusion protein is demonstrated to be sufficient for the efficient preparation of galactosylated oligosaccharides from inexpensive UDP-glucose in a multigram scale. Lysates containing the fusion protein are also found to be useful in the production of more complex oligosaccharides in coupled reaction mixtures, e.g., in the preparation of sialosides from N-acetylglucosamine. Thus, bacterially expressed fusion protein is well suited for the facile and economic preparation of natural oligosaccharides and synthetic derivatives based on the lactosamine core.

Facile preparation of indoxyl- and nitrophenyl glycosides of lactosamine and isolactosamine

The synthesis of the novel indoxyl glycosides of N-acetyl-lactosamine (X-LacNAc) and N-acetyl-isolactosamine (X-LNB) is reported employing glycosyl chlorides in a facile phase transfer glycosylation, followed by mild decarboxylation and finally deacetylat

Synthesis and utility of sulfated chromogenic carbohydrate model substrates for measuring activities of mucin-desulfating enzymes

A chromogenic substrate, 4-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside 6-sodium sulfate was synthesized and used in combination with β-N-acetylhexosaminidase for detection of the sulfatase, MdsA, by release of 4-nitrophenol. MdsA was originally isolated from the bacterium Prevotella strain RS2 and is believed to be involved in desulfation of sulfomucins, major components of the mucus barrier protecting the human colon surface. The exo nature of the MdsA sulfatase was indicated by its inability to de-esterify the disaccharide 4-nitrophenyl β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D- glucopyranoside 6-sodium sulfate. This latter compound was prepared from monosaccharide precursors by two different methods, the shorter requiring just six steps from 4-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside and giving an overall yield of 26.4%. The syntheses of 4-nitrophenyl β-D-galactopyranoside 3-triethylammonium sulfate and 6-triethylammonium sulfate and their use in combination with β-galactosidase as chromogenic substrates for detecting Bacteroides fragilis sulfatases with different specificities was also demonstrated.