sodium (2S,4S,5R,6R)-5-acetamido-4-hydroxy-2-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methoxy}-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

• ChemBase ID: 153524
• Molecular Formular: C23H38NNaO19
• Molecular Mass: 655.53289
• Monoisotopic Mass: 655.19357228
• SMILES: CC(=O)N[C@@H]1[C@H](C[C@](O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)[O-])OC[C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)O)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)O.[Na+]
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1O[C@@](OC[C@H]2OC(O)[C@@H]([C@H]([C@@H]2O[C@@H]2O[C@H](CO)[C@@H]([C@@H]([C@H]2O)O)O)O)O)(C[C@@H]([C@H]1NC(=O)C)O)C(=O)[O-])O)O.[Na+]
• InChI: InChI=1S/C23H39NO19.Na/c1-6(27)24-11-7(28)2-23(22(37)38,43-19(11)12(30)8(29)3-25)39-5-10-18(15(33)16(34)20(36)40-10)42-21-17(35)14(32)13(31)9(4-26)41-21;/h7-21,25-26,28-36H,2-5H2,1H3,(H,24,27)(H,37,38);/q;+1/p-1/t7-,8+,9+,10+,11+,12+,13-,14-,15+,16+,17+,18+,19+,20?,21-,23-;/m0./s1
• InChIKey: FLXUDTRTHITHST-UHWLIUQISA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,4S,5R,6R)-5-acetamido-4-hydroxy-2-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methoxy}-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• IUPAC Traditional name: sodium (2S,4S,5R,6R)-5-acetamido-4-hydroxy-2-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methoxy}-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• Synonyms: α-NeuNAc-(2→6)-β-D-Gal-(1→4)-D-Glc; 6′-N-Acetylneuraminyl-lactose sodium salt; 6′-SL; 6′-Sialyllactose sodium salt

Database IDs

• CAS Number: 74609-39-5
• PubChem SID: 24891426; 162247663
• PubChem CID: 23679057

CALCULATED PROPERTIES

• Acid pKa: 2.8223083
• H Acceptors: 19
• H Donor: 12
• LogD (pH = 5.5): -9.72705
• LogD (pH = 7.4): -10.597927
• Log P: -7.105609
• Molar Refractivity: 139.4451 cm^3
• Polarizability: 53.76653 Å^3
• Polar Surface Area: 337.91 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPAE/PAD)
• Biological Source: from human milk
• Linear Formula: C23H38NO19Na

DETAILS

Sigma Aldrich - A9204

Application
6′-Sialyllactose is a compound wherein the acetylneuraminyl (NANA) unit is connected to the galactosyl unit of lactose at the 6 position. In 3’-sialylactose, this connection is at the 3 position. 3′-Sialyllactose and 6′-Sialyllactose are used to differentiate and characterize binding domains of viruses, such as influenza and rhinitis viruses, that recognize NANA capped cell surface receptors. 3′-Sialyllactose and 6’-sialylactose are used as reference compounds in analytical methods developed to measure their presence in materials such as milk and colostrums.