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

• ChemBase ID: 109280
• Molecular Formular: C8H15NO6
• Molecular Mass: 221.2078
• Monoisotopic Mass: 221.08993721
• SMILES: CC(=O)N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O
• Canonical SMILES: OC[C@H]1OC(O)[C@@H]([C@H]([C@H]1O)O)NC(=O)C
• InChI: InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6+,7-,8?/m1/s1
• InChIKey: OVRNDRQMDRJTHS-KEWYIRBNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-acetyl-D-galactosamine; GalNAc
• Synonyms: N-ACETYLGALACTOSAMINE; 2-Acetamido-2-deoxy-D-galactose; D-GalNAc; N-Acetylchondrosamine; N-Acetyl-D-galactosamine; N-((3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxyMethyl)tetrahydro-2H-pyran-3-yl)acetaMide; GalNAc; N-Acetyl-2-amino-2-deoxy-D-galactose; N-Acetyl-D-galactosamine; N-乙酰基-D-半乳糖胺

Database IDs

• CAS Number: 14215-68-0; 1811-31-0
• EC Number: 217-321-9
• MDL Number: MFCD00065372
• Beilstein Number: 2331340
• PubChem SID: 162095049; 24890693
• PubChem CID: 35717

CALCULATED PROPERTIES

• Acid pKa: 11.60413
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.2205749
• LogD (pH = 7.4): -3.2206008
• Log P: -3.2205744
• Molar Refractivity: 47.0247 cm^3
• Polarizability: 19.398714 Å^3
• Polar Surface Area: 119.25 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, colorless; Water
• Apperance: Off-White Solid
• Melting Point: 155-158°C
• Optical Rotation: [α]20/D +85±5°, 5 hr, c = 1% in H2O

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ~98%; ≥98.0% (sum of enantiomers, HPLC); 98%
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C8H15NO6

DETAILS

MP Biomedicals - 05210443

MP Biomedicals Rare Chemical collection

Sigma Aldrich - A2795

包装
10 mg in autosmp vl
Application
N-Acetyl-D-galactosamine (GalNAc), an aminosugar, is a component of many O-linked and N-linked glycan structures. As UDP-GalNAc, GalNAc is the intial O-linked sugar to many serine and threonine residues in protein glycosylations.

Sigma Aldrich - 01139

Other Notes
Synthetic uses1,2

REFERENCES

• Nakajima, M., et al.: App. Microbiol. Biotechnol., 83, 109 (2009)
• Singh, S., et al.: Mol. Immunol., 46, 1240 (2009)