[(2R,3R,4R,5R)-3,4,6-tris(acetyloxy)-5-(2-azidoacetamido)oxan-2-yl]methyl acetate

• ChemBase ID: 153890
• Molecular Formular: C16H22N4O10
• Molecular Mass: 430.36668
• Monoisotopic Mass: 430.13359292
• SMILES: CC(=O)OC[C@@H]1[C@@H]([C@@H]([C@H](C(O1)OC(=O)C)NC(=O)CN=[N+]=[N-])OC(=O)C)OC(=O)C
• Canonical SMILES: [N-]=[N+]=NCC(=O)N[C@H]1C(OC(=O)C)O[C@@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)COC(=O)C
• InChI: InChI=1S/C16H22N4O10/c1-7(21)26-6-11-14(27-8(2)22)15(28-9(3)23)13(16(30-11)29-10(4)24)19-12(25)5-18-20-17/h11,13-16H,5-6H2,1-4H3,(H,19,25)/t11-,13-,14+,15-,16?/m1/s1
• InChIKey: HGMISDAXLUIXKM-YJUJGKJLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4R,5R)-3,4,6-tris(acetyloxy)-5-(2-azidoacetamido)oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4R,5R)-3,4,6-tris(acetyloxy)-5-(2-azidoacetamido)oxan-2-yl]methyl acetate
• Synonyms: GalNaz; N-Azidoacetylgalactosamine, Acetylated; 乙酰化 N-叠氮乙酰半乳糖胺

Database IDs

• PubChem SID: 162248029
• PubChem CID: 71311754

CALCULATED PROPERTIES

• Acid pKa: 11.7322855
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): -1.5670222
• LogD (pH = 7.4): -1.56704
• Log P: -1.4529763
• Molar Refractivity: 91.6254 cm^3
• Polarizability: 37.22371 Å^3
• Polar Surface Area: 172.96 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

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

Product Information

• Empirical Formula (Hill Notation): C16H22N4O10

DETAILS

Sigma Aldrich - A7480

Application
An unnatural azido sugar that can be introduced metabolically in model organisms and subsequently incorporates in glycan structures. The azide group will react with phosphines linked to agents for visualization or selective capture. To be used in conjunction with the FLAG®-Phosphine™ (GPHOS1) that is compatible with many additional FLAG tools for both applications.
Legal Information
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