13089-18-4

Basic information

• Product Name: PHENYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GALACTOPYRANOSIDE
• Synonyms: 1-PHENYL-2-ACETAMIDO-2-DEOXY-ALPHA-D-GALACTOSIDE;2-PHENYL-2-ACETAMIDO-ALPHA-D-DEOXYGALACTOPYRANOSIDE;PHENYL N-ACETYL-ALPHA-D-GALACTOSAMINIDE;PH-ALPHA-D-GALNAC;PHENYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GALACTOPYRANOSIDE;phenyl N-acetyl-A-D-galactosaminide;phenyl 2-acetamido-2-deoxy-α-d-galactopyranoside;phenyl n-acetyl-α-d-galactosaminide
• CAS NO: 13089-18-4
• Molecular Formula: C₁₄H₁₉NO₆
• Molecular Weight: 297.3
• EINECS: 236-000-4
• Product Categories: Sugars, Carbohydrates & Glucosides
• Mol File: 13089-18-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 248℃ (decomposition)
• Boiling Point: 600.8°Cat760mmHg
• Flash Point: 317.2°C
• Appearance: /
• Density: 1.38g/cm³
• Vapor Pressure: 2.77E-15mmHg at 25°C
• Refractive Index: 1.598
• Storage Temp.: 2-8°C
• CAS DataBase Reference: PHENYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GALACTOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GALACTOPYRANOSIDE(13089-18-4)
• EPA Substance Registry System: PHENYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GALACTOPYRANOSIDE(13089-18-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 13089-18-4(Hazardous Substances Data)

Usage

Uses

Phenyl 2-Acetamido-2-deoxy-a-D-galactopyranoside is a useful intermediate for the asymmetric synthesis of complex oligosaccharides.

InChI:InChI=1/C14H19NO6/c1-8(17)15-11-13(19)12(18)10(7-16)21-14(11)20-9-5-3-2-4-6-9/h2-6,10-14,16,18-19H,7H2,1H3,(H,15,17)

Upstream product

• 108-95-2 phenol 
• 593260-66-3 phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-8-α-D-galactopyranoside 
• 211621-55-5 3,4,6-tri-O-benzyl-2-nitro-D-galactal 
• 76375-60-5 (3R,4R,5R,6R)-3-acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate 
• 13089-43-5 phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranoside 
• 593260-70-9 phenyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-galatopyranoside 
• 3006-60-8 1,3,4,6-tetra-O-acetyl-2-acetamido-2-deoxy-α,β-D-mannopyranose 
• 4148-73-6 phenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-mannopyranoside 
• 72-87-7 N-acetyl-D-mannosamine 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-mannopyrano)-[2,1:4',5']-2-oxazoline 

Downstream Products

• 108-95-2 phenol 
• 865353-12-4 phenyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-α-D-galactopyranoside 
• 865096-55-5 phenyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside 
• 13089-43-5 phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranoside 

Relevant articles and documents

A mechanistic study on the α-N-acetylgalactosaminidase from E. meningosepticum: A family 109 glycoside hydrolase

A recombinant glycoside hydrolase family 109 α-N- acetylgalactosaminidase from the pathogenic bacteria E. meningosepticum catalyses the hydrolysis of aryl 2-acetamido-2-deoxy-α-d- galactopyranosides. The sensitivities to leaving group abilities (βlg values) on V and V/K are -0.08 ± 0.06 and -0.31 ± 0.12, respectively. These results are consistent with an E2 elimination following hydride transfer from C3. This journal is the Partner Organisations 2014.

Synthesis of sulfated phenyl 2-acetamido-2-deoxy-D-galactopyranosides. 4-O-Sulfated phenyl 2-acetamido-2-deoxy-β-D-galactopyranoside is a competitive acceptor that decreases sulfation of chondroitin sulfate by N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase

We have previously cloned N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase (GalNAc4S-6ST), which transfers sulfate from 3′-phosphoadenosine 5′-phosphosulfate (PAPS) to the C-6 hydroxyl group of the GalNAc 4-sulfate residue of chondroitin sulfate A and forms chondroitin sulfate E containing GlcA-GalNAc(4,6-SO4) repeating units. To investigate the function of chondroitin sulfate E, the development of specific inhibitors of GalNAc4S-6ST is important. Because GalNAc4S-6ST requires a sulfate group attached to the C-4 hydroxyl group of the GalNAc residue as the acceptor, the sulfated GalNAc residue is expected to interact with GalNAc4S-6ST and affect its activity. In this study, we synthesized phenyl α- or -β-2-acetamido-2-deoxy-β-D-galactopyranosides containing a sulfate group at the C-3, C-4, or C-6 hydroxyl groups and examined their inhibitory activity against recombinant GalNAc4S-6ST. We found that phenyl β-GalNAc(4SO4) inhibits GalNAc4S-6ST competitively and also serves as an acceptor. The sulfated product derived from phenyl β-GalNAc(4SO4) was identical to phenyl β-GalNAc(4,6-SO 4). These observations indicate that derivatives of β-D-GalNAc(4SO4) are possible specific inhibitors of GalNAc4S-6ST.