144683-69-2

Basic information

• Product Name: p-nitrophenyl O-β-D-galactopyranosyl-(1->3)-β-D-xylopyranoside
• Synonyms: p-nitrophenyl O-β-D-galactopyranosyl-(1->3)-β-D-xylopyranoside
• CAS NO: 144683-69-2
• Molecular Weight: 433.369
• Mol File: 144683-69-2.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: p-nitrophenyl O-β-D-galactopyranosyl-(1->3)-β-D-xylopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: p-nitrophenyl O-β-D-galactopyranosyl-(1->3)-β-D-xylopyranoside(144683-69-2)
• EPA Substance Registry System: p-nitrophenyl O-β-D-galactopyranosyl-(1->3)-β-D-xylopyranoside(144683-69-2)

Safety Data

• Hazardous Substances Data: 144683-69-2(Hazardous Substances Data)

Upstream product

• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 
• 24624-78-0 1-O-(4-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-xylopyranoside 
• 87-72-9 D-Xylose 
• 25878-60-8 D-galactose pentaacetate 
• 439-03-2 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl fluoride 
• 4163-45-5 2,3,4,6-tetra-O-acetyl-β-galactopyranosyl fluoride 
• 3068-32-4 1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose 
• 2021-84-3 α-galactosyl fluoride 
• 2001-96-9 p-nitrophenyl β-D-xylopyranoside 
• 2816-24-2 o-nitrophenyl D-galactopyranoside 
• 2021-62-7 β-D-galactopyranosyl fluoride 
• 249928-93-6 (3-nitro-2-pyridyl) β-D-galactopyranoside 
• 250129-74-9 5-nitro-2-pyridyl β-D-galactoside 
• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 

Relevant articles and documents

Chemoenzymatic synthesis of Gal(β1-3)Gal(β1-4)Xyl(β)-L-Ser and Gal(β1-3)Gal(β1-4)Xyl(β)-MU by the use of β-D-galactosidase

The title trisaccharide-serine conjugate 1 constituting the linkage region between glycosaminoglycan and protein in proteoglycan, was synthesized via a trisaccharide p-nitrophenyl (PNP) glycoside prepared by stepwise enzymatic transglycosidation to Xyl-PNP with a β-D-galactosidase. In the second transglycosidation step, partial protection of the disaccharide intermediate, Gal-Xyl-PNP, furnished selective galactosylation at the 3'-position. Cleavage of the PNP group after peracetylation, chemical coupling with serine and final deprotection afforded 1. Fluorescence labeled trisaccharide, Gal(β1-3)Gal(β1-4)Xyl(β)-MU (MU: 4-methylumbelliferyl) (2) was also synthesized in a simalar way.

Acceptor-dependent regioselectivity of glycosynthase reactions by Streptomyces E383A β-glucosidase

The nonnucleophilic mutant E383A β-glucosidase from Streptomyces sp. has proven to be an efficient glycosynthase enzyme, catalyzing the condensation of α-glucosyl and α-galactosyl fluoride donors to a variety of acceptors. The enzyme has maximal activity

Chemoenzymatic synthesis of a trisaccharide-serine conjugate, gal(β1-3)gal(β1-4)xyl(β1-o)-l-ser, use of galactosyl fluoride as a donor for transglycosylation

The trisaccharide - serine conjugate [Gal(β1-3)Gal(β1-4)Xyl(β-Ser], constituting the linkage region between the glycosaminoglycan and protein in proteoglycan, was synthesized by using enzymatic transglycosylation with a β-D-galactosidase as a key reaction. The yields of transglycosylation were much improved by using galactosyl fluoride as a donor in comparison with those obtained by a conventional p-nitrophenyl (PNP) galactoside. After enzymatic synthesis of Gal(β1-3)Gal(β1-4)Xyl(β)-PNP, cleavage of the PNP group of the fully acetylated trisaccharide, chemical coupling with serine, and final deprotection afforded Gal(β1-3)Gal(β1-4)Xyl(β)-Ser.