20972-29-6

Basic information

• Product Name: BETA-D-GAL-[1->3]-D-GALNAC
• Synonyms: T ANTIGEN;THOMSEN-FRIEDENREICH ANTIGEN;TF ANTIGEN;2-ACETAMIDO-2-DEOXY-3-O-(BETA-D-GALACTOPYRANOSYL)-D-GALACTOPYRANOSE;2-ACETAMIDO-2-DEOXY-3-O-(BETA-D-GALACTOPYRANOSYL)-D-GALACTOSE;BETA-1,3-GALACTOSYL-N-ACETYL GALACTOSAMINE;BETA-D-GAL-[1->3]-D-GALNAC;GAL1-B-3GALNAC
• CAS NO: 20972-29-6
• Molecular Formula: C₁₄H₂₅NO₁₁
• Molecular Weight: 383.35
• Product Categories: Oligosaccharide Compounds
• Mol File: 20972-29-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 159-160
• Boiling Point: 795.5 °C at 760 mmHg
• Flash Point: 434.9 °C
• Appearance: White crystalline solid
• Density: 1.64 g/cm³
• Vapor Pressure: 2.95E-29mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: −20°C
• CAS DataBase Reference: BETA-D-GAL-[1->3]-D-GALNAC(CAS DataBase Reference)
• NIST Chemistry Reference: BETA-D-GAL-[1->3]-D-GALNAC(20972-29-6)
• EPA Substance Registry System: BETA-D-GAL-[1->3]-D-GALNAC(20972-29-6)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 20972-29-6(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C14H25NO11/c1-4(18)15-7-12(9(20)6(3-17)24-13(7)23)26-14-11(22)10(21)8(19)5(2-16)25-14/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5-,6-,7-,8+,9+,10+,11-,12-,13?,14+/m1/s1

Upstream product

• 7512-17-6 N-Acetyl-D-glucosamine 
• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 
• 72-87-7 N-acetyl-D-galactosamine 
• 1144040-14-1 4-nitrophenyl (β-D-galactopyranosyl)-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranoside 
• 57467-13-7 4-nitrophenyl (O-β-D-galactopyranosyl)-(1-3)-2-acetamido-2-deoxy-β-D-glucopyranoside 

Downstream Products

• 57467-13-7 4-nitrophenyl (O-β-D-galactopyranosyl)-(1-3)-2-acetamido-2-deoxy-β-D-glucopyranoside 
• 710306-57-3 4-nitrophenyl 2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 1314876-73-7 α-D-mannopyranosyl-(1->3)-2-amino-1,2-deoxy-1-(2-triphenylmethylthioeth-2-ylamino)-D-glucitol 
• 117773-04-3 O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic-acid)-(2-3)-O-β-D-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-β-D-galactopyranose 
• 117249-18-0 O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic-acid)-(2-3)-O-β-D-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-α-D-galactopyranose 
• 142434-22-8 O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic-acid)-(2-3)-O-β-D-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-β-D-glucopyranose 
• 142434-21-7 O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic-acid)-(2-3)-O-β-D-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-α-D-glucopyranose 

Relevant articles and documents

Syntheses of mucin-type O-glycopeptides and oligosaccharides using transglycosylation and reverse-hydrolysis activities of Bifidobacterium endo-α-N-acetylgalactosaminidase

Endo-α-N-acetylgalactosaminidase catalyzes the release of Galβ1-3GalNAc from the core 1-type O-glycan (Galβ1-3GalNAcα1- Ser/Thr) of mucin glycoproteins and synthetic p-nitrophenyl (pNP) α-linked substrates. Here, we report the enzymatic syntheses of core 1 disaccharide-containing glycopeptides using the transglycosylation activity of endo-α-N-acetylgalactosaminidase (EngBF) from Bifidobacterium longum. The enzyme directly transferred Galβ1-3GalNAc to serine or threonine residues of bioactive peptides such as PAMP-12, bradykinin, peptide-T and MUC1a when Galβ1-3GalNAcα1-pNP was used as a donor substrate. The enzyme was also found to catalyze the reverse-hydrolysis reaction. EngBF synthesized the core 1 disaccharide-containing oligosaccharides when the enzyme was incubated with either glucose or lactose and Galβ1-3GalNAc prepared from porcine gastric mucin using bifidobacterial cells expressing endo-α-N- acetylgalactosaminidase. Synthesized oligosaccharides are promising prebiotics for bifidobacteria.

Highly efficient enzymatic synthesis of Galβ-(1→3)-GalNAc and Galβ-(1→3)-GlcNAc in ionic liquids

Ionic liquids (ILs) have emerged as an alternative to conventional organic media due to their high thermal and chemical stability, negligible vapour pressure, non-flammability and easy recycling. In this context, this work assesses the catalytic activity of a β-galactosidase from Bacillus circulans ATCC 31382 (β-Gal-3-NTag) in the synthesis of β-(1→3)-galactosides using different ILs. A noticeably increase in activity, retaining total regioselectivity was found in the synthetic behaviour of B. circulans β-galactosidase in ILs as co-solvents and using a 1:5 molar ratio of donor (pNP-β-Gal):acceptor (GlcNAc or GalNac). Yields up to 97% of β-(1→3) with different ILs were found. These reactions take place without noticeable hydrolytic activity and with total regioselectivity, representing a considerable improvement over the use of aqueous buffer or conventional organic solvents. Furthermore, reaction scaling up and IL recovery and recycling are feasible without losing catalytic action. Molecular modelling studies performed predict a three-dimensional interaction at the active centre between the acceptor and the water-IL mixture, which could explain the results obtained.