(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride

• ChemBase ID: 119244
• Molecular Formular: C6H14ClNO5
• Molecular Mass: 215.63206
• Monoisotopic Mass: 215.05605023
• SMILES: [C@H]1([C@H]([C@@H]([C@H](OC1O)CO)O)O)N.Cl
• Canonical SMILES: OC[C@H]1OC(O)[C@@H]([C@H]([C@@H]1O)O)N.Cl
• InChI: InChI=1S/C6H13NO5.ClH/c7-3-5(10)4(9)2(1-8)12-6(3)11;/h2-6,8-11H,1,7H2;1H/t2-,3-,4-,5-,6?;/m1./s1
• InChIKey: QKPLRMLTKYXDST-NSEZLWDYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride
• IUPAC Traditional name: (3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride; glucosamine hydrochloride
• Synonyms: (3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol hydrochloride; D-(+)-Glucosamine hydrochloride; (3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride; 2-Amino-2-deoxy-D-glucose hydrochloride; Chitosamine hydrochloride; 2-氨基-2-脱氧-D-葡萄糖 盐酸盐; 壳糖胺 盐酸盐; D-(+)-葡萄糖胺 盐酸盐

Database IDs

• CAS Number: 66-84-2
• EC Number: 200-638-1
• MDL Number: MFCD00050671; MFCD00135831
• Beilstein Number: 4157370
• PubChem SID: 24895066; 162102975; 24895187
• PubChem CID: 2723635

CALCULATED PROPERTIES

• Acid pKa: 11.726975
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -5.5965767
• LogD (pH = 7.4): -3.9292529
• Log P: -3.039421
• Molar Refractivity: 37.5809 cm^3
• Polarizability: 15.959335 Å^3
• Polar Surface Area: 116.17 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, colorless
• Apperance: crystalline
• Melting Point: ≥300 °C; 190-194 °C (dec.)(lit.)
• Optical Rotation: [α]20/D +72.5±2°, 24 hr, c = 2% in H2O
• Hydrophobicity(logP): -2.184

Safety Information

• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99%; ≥99.0% (HPLC); 95%
• Salt Data: HCl
• Suitability: suitable for cell culture
• Ignition Residue: ≤0.05%
• Empirical Formula (Hill Notation): C6H13NO5 · HCl

DETAILS

Sigma Aldrich - G1514

Application
Supplementation of cell culture media with glucosamine may enhance N-glycosylation of secreted proteins and affect differentiation of cell lines such as chondocytes and stem cells.
Biochem/physiol Actions
Glucosamine, an amino sugar, is the precursor of the hexosamine biosynthetic pathway leading to the formation of UDP-N-acetylglucosamine (UDP-GlcNAc), which is then used for making glycosaminoglycans, proteoglycans, and glycolipids.

Sigma Aldrich - G4875

包装
1 kg in poly bottle
10 mg in autosmp vl
25, 100, 500 g in poly bottle

Sigma Aldrich - 49130

Biochem/physiol Actions
Glucosamine, an amino sugar, is the precursor of the hexosamine biosynthetic pathway leading to the formation of UDP-N-acetylglucosamine (UDP-GlcNAc), which is then used for making glycosaminoglycans, proteoglycans, and glycolipids. D-(+)-Glucosamine inhibits the coaggregation of Candida yeast species with the bacterial strain S. salivarius. 1