(2R,3R,4S,5R)-2-amino-3,4,5,6-tetrahydroxyhexanoic acid

• ChemBase ID: 110244
• Molecular Formular: C6H13NO6
• Molecular Mass: 195.17052
• Monoisotopic Mass: 195.07428714
• SMILES: N[C@H]([C@@H](O)[C@H](O)[C@H](O)CO)C(=O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H]([C@H](C(=O)O)N)O)O)O
• InChI: InChI=1S/C6H13NO6/c7-3(6(12)13)5(11)4(10)2(9)1-8/h2-5,8-11H,1,7H2,(H,12,13)/t2-,3-,4-,5-/m1/s1
• InChIKey: UFYKDFXCZBTLOO-TXICZTDVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-amino-3,4,5,6-tetrahydroxyhexanoic acid
• IUPAC Traditional name: glucosaminate; (2R,3R,4S,5R)-2-amino-3,4,5,6-tetrahydroxyhexanoic acid
• Synonyms: D-Glucopyranose; Glucopyranose; NSC 287045; D-Glucose; GLUCOSAMINIC ACID; 2-Amino-2-deoxy-D-gluconic acid; D-Glucosaminic acid

Database IDs

• CAS Number: 3646-68-2; 2280-44-6
• EC Number: 222-879-1
• MDL Number: MFCD00037764
• Beilstein Number: 1726033
• PubChem SID: 162095757; 24895011
• PubChem CID: 73563

CALCULATED PROPERTIES

• Acid pKa: 1.8132119
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -5.7776766
• LogD (pH = 7.4): -5.824321
• Log P: -5.777404
• Molar Refractivity: 39.9285 cm^3
• Polarizability: 16.609613 Å^3
• Polar Surface Area: 144.24 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 152-155°C; 235-245 °C (dec.)
• Optical Rotation: [α]20/D -15±2°, c = 1% in 1 M HCl

Safety Information

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

Product Information

• Purity: ≥98%; ≥99.0% (T)
• Empirical Formula (Hill Notation): C6H13NO6

DETAILS

MP Biomedicals - 05214225

MP Biomedicals Rare Chemical collection

Toronto Research Chemicals - G595000

Used in enzymic synthesis of cyclohexyl-α and β-D-glucosides.

REFERENCES

• Wang, R., et al.: J. Mol. Catal. B. Enz., 56, 131 (2009)