N-[2-(benzyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

• ChemBase ID: 132684
• Molecular Formular: C15H21NO6
• Molecular Mass: 311.33034
• Monoisotopic Mass: 311.1368874
• SMILES: CC(=O)NC1C(C(C(OC1OCc1ccccc1)CO)O)O
• Canonical SMILES: OCC1OC(OCc2ccccc2)C(C(C1O)O)NC(=O)C
• InChI: InChI=1S/C15H21NO6/c1-9(18)16-12-14(20)13(19)11(7-17)22-15(12)21-8-10-5-3-2-4-6-10/h2-6,11-15,17,19-20H,7-8H2,1H3,(H,16,18)
• InChIKey: SKOZFDIGKDPQBO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[2-(benzyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[2-(benzyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: α-D-GalNAc-1→OCH2Ph; Benzyl N-acetyl-α-D-galactosaminide; Benzyl-α-GalNAc; GalNAc α-O-benzyl; GalNAc-O-bn; Benzyl 2-acetamido-2-deoxy-α-D-galactopyranoside

Database IDs

• CAS Number: 3554-93-6
• MDL Number: MFCD00057920
• PubChem SID: 24891802; 162226961
• PubChem CID: 561184

CALCULATED PROPERTIES

• Acid pKa: 12.357337
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.8529751
• LogD (pH = 7.4): -0.8529792
• Log P: -0.8529748
• Molar Refractivity: 76.3885 cm^3
• Polarizability: 30.718012 Å^3
• Polar Surface Area: 108.25 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - B4894

Application
Benzyl 2-acetamido-2-deoxy-α-D-galactopyranoside (BADGP), an O-GlcNAc (OGT) transferase inhibitor, is used to study the physiological effects of O-glycosylation modulation.
Biochem/physiol Actions
Benzyl-N-acetyl-α-galactosaminide inhibits glycosyltransferase incorporation of glucosamine into O-glycans. Suppresses mucin biosynthesis1,2 and inhibits MUC1 expression in breast cancer cell line MDF-7.3