59837-14-8

Basic information

• Product Name: P-NITROPHENYL 2-ACETAMIDO-2-DEOXY-3-O-(BETA-D-GALACTOPYRANOSYL)-ALPHA-D-GALACTOPYRANOSIDE
• Synonyms: T ANTIGEN, P-NITROPHENYL-;P-NITROPHENYL 2-ACETAMIDO-2-DEOXY-3-O-(B-D-GALACTOPYRANOSYL)-A-D-GALACTOPYRANOSIDE;P-NITROPHENYL 2-ACETAMIDO-2-DEOXY-3-O-(BETA-D-GALACTOPYRANOSYL)-ALPHA-D-GALACTOPYRANOSIDE;BETA-D-GAL-[1->3]-ALPHA-D-GALNAC-1->OC6H4NO2-P;GAL-BETA1,3GALNAC-ALPHA-PNP;GAL1-B-3GALNAC-A-PNP;P-nitrophenyl 2-acetamido-2-deoxy-3-O-*(B-D-galac;P-NITROPHENYL 2-ACETAMIDO-2-DEOXY-3-O-*( B-D-GALACTO
• CAS NO: 59837-14-8
• Molecular Formula: C₂₀H₂₈N₂O₁₃
• Molecular Weight: 504.44
• EINECS: 1533716-785-6
• Product Categories: Oligosaccharides;substrate
• Mol File: 59837-14-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 225-228°C dec.
• Boiling Point: 879oC at 760 mmHg
• Flash Point: 485.4oC
• Appearance: /
• Density: 1.61g/cm3
• Vapor Pressure: 4.5E-33mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: −20°C
• Solubility: Methanol (Slightly, Heated, Sonicated), Water (Slightly, Heated, Sonicated)
• PKA: 12.67±0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: P-NITROPHENYL 2-ACETAMIDO-2-DEOXY-3-O-(BETA-D-GALACTOPYRANOSYL)-ALPHA-D-GALACTOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: P-NITROPHENYL 2-ACETAMIDO-2-DEOXY-3-O-(BETA-D-GALACTOPYRANOSYL)-ALPHA-D-GALACTOPYRANOSIDE(59837-14-8)
• EPA Substance Registry System: P-NITROPHENYL 2-ACETAMIDO-2-DEOXY-3-O-(BETA-D-GALACTOPYRANOSYL)-ALPHA-D-GALACTOPYRANOSIDE(59837-14-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 59837-14-8(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

Uses

Acetylgalactosaminidase sequence substrate Clostridium Bifidobacterium. A fluorescent substrate for α2,3-(O)-Sialyltransferase

InChI:InChI=1/C20H28N2O13/c1-8(25)21-13-18(35-20-17(29)16(28)14(26)11(6-23)34-20)15(27)12(7-24)33-19(13)32-10-4-2-9(3-5-10)22(30)31/h2-5,11-20,23-24,26-29H,6-7H2,1H3,(H,21,25)/t11-,12-,13-,14+,15+,16+,17-,18?,19+,20+/m1/s1

Upstream product

• 1147438-51-4 p-nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranoside 
• 100-02-7 4-nitro-phenol 
• 1316823-14-9 p-nitrophenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->3)-2-azido-2-deoxy-4,6-O-p-methoxybenzylidene-α-D-galactopyranoside 
• 1316823-21-8 p-nitrophenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->3)-2-azido-2-deoxy-α-D-galactopyranoside 
• 210418-04-5 C₁₂H₁₄N₄O₇ 
• 1316822-99-7 p-nitrophenyl 2-azido-2-deoxy-4,6-O-p-methoxybenzylidene-α-D-galactopyranoside 
• 83025-20-1 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyltrichloroacetimidate 
• 2021-84-3 α-galactosyl fluoride 
• 50645-66-4 4-nitrophenyl α-D-2-N-acetyl-galactosaminide 
• 23646-68-6 4-nitrophenyl 2-acetamido-2-deoxy-α-D-galactopyranoside 
• 2816-24-2 o-nitrophenyl D-galactopyranoside 
• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 

Downstream Products

• 162792-49-6 p-aminophenyl β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside 
• 60280-58-2 O-[2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine 
• 60280-57-1 3-O-(2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl)-L-serine 

Relevant articles and documents

Characterization of a galactosynthase derived from bacillus circulans β-galactosidase: Facile synthesis of D -lacto- and D -galacto-N-bioside

Glycosynthases - retaining glycosidases mutated at their catalytic nucleophile - catalyze the formation of glycosidic bonds from glycosyl fluorides as donor sugars and various glycosides as acceptor sugars. Here the first glycosynthase derived from a family 35 β-galactosidase is described. The Glu→Gly mutant of BgaC from Bacillus circulans (BgaC-E233G) catalyzed regioselective galactosylation at the 3-position of the sugar acceptors with α-galactosyl fluoride as the donor. Transfer to 4-nitophenyl α-D-N-acetyl-glucosaminide and α-D-N-acetylgalactosaminide yielded 4-nitophenyl α-lacto-N-biose and α-galacto-N-biose, respectively, in high yields (up to 98 %). Kinetic analysis revealed that the high affinity of the acceptors contributed mostly to the BgaC-E233G-catalyzed transglycosylation. BgaC-E233G showed no activity with β-(1,3)-linked disaccharides as acceptors, thus suggesting that this enzyme can be used in one-pot synthesis of LNB- or GNB-containing glycans. The first glycosynthase from family 35 β-galactosidase: A β-galactosidase from Bacillus circulans (BgaC) was converted into a glycosynthase that catalyzes regioselective galactosylation at the 3-OH group of sugar acceptors. The yields were almost quantitative: up to 98 % lacto-N-bioside and galacto-N-bioside were obtained.

Regioselective synthesis of p-nitrophenyl glycosides of β-D-galactopyranosyl-disaccharides by transglycosylation with β-D-galactosidases

The β-D-galactosidase from porcine liver induced regiospecific transglycosylation of β-D-galactose from β-D-Gal-OC6H4NO2-o to OH-6 of, respectively, p-nitrophenyl glycoside acceptors of Gal, GlcNAc and GalNAc to afford β-G