N-[(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamide

• ChemBase ID: 119034
• Molecular Formular: C8H15NO6
• Molecular Mass: 221.2078
• Monoisotopic Mass: 221.08993721
• SMILES: [C@@H]([C@@H](NC(=O)C)C=O)([C@@H]([C@H](O)CO)O)O
• Canonical SMILES: O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)NC(=O)C
• InChI: InChI=1S/C8H15NO6/c1-4(12)9-5(2-10)7(14)8(15)6(13)3-11/h2,5-8,11,13-15H,3H2,1H3,(H,9,12)/t5-,6+,7+,8+/m0/s1
• InChIKey: MBLBDJOUHNCFQT-LXGUWJNJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamide
• IUPAC Traditional name: N acetylglucosamine
• Synonyms: N-((2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl)acetamide; N-Acetyl-D-glucosamine–Agarose; 2-Acetamido-2-deoxy-D-glucose

Database IDs

• CAS Number: 7512-17-6
• MDL Number: MFCD00136044
• PubChem SID: 24890642; 162103160
• PubChem CID: 1738118

CALCULATED PROPERTIES

• Acid pKa: 12.087925
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.856396
• LogD (pH = 7.4): -3.8564038
• Log P: -3.8563957
• Molar Refractivity: 48.4469 cm^3
• Polarizability: 19.496147 Å^3
• Polar Surface Area: 127.09 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: saline suspension

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: 95+%
• Description: Ring-Chain Tautomers
• Binding Capacity: 25-50 mg/mL binding capacity (Triticum vulgaris lectin)
• Matrix: 6% beaded agarose
• Matrix Spacer: 5 atoms
• Matrix Activation: divinyl sulfone
• Matrix Attachment: hydroxyl
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - A2278

Application
Used to purify wheat germ (Triticum vulgaris) lectin.
N-Acetyl-D-glucosamine is used in affinity chromatography, protein chromatography and carbohydrate matrices. N-Acetyl-D-glucosamine can be used to purify wheat germ (Triticum vulgaris) lectin.
Physical form
Suspension in 0.15 M NaCl, 0.01 M sodium phosphate, pH 6.8, containing 0.02% sodium azide