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

• ChemBase ID: 155799
• Molecular Formular: C23H39NO19
• Molecular Mass: 633.55106
• Monoisotopic Mass: 633.21162803
• 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@@H](O1)O[C@@H]1[C@H](OC([C@@H]([C@H]1O)O)O)CO)O)O)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1O[C@@](OC[C@H]2O[C@@H](O[C@@H]3[C@@H](CO)OC([C@@H]([C@H]3O)O)O)[C@@H]([C@H]([C@H]2O)O)O)(C[C@@H]([C@H]1NC(=O)C)O)C(=O)O)O)O
• InChI: InChI=1S/C23H39NO19/c1-6(27)24-11-7(28)2-23(22(37)38,43-19(11)12(30)8(29)3-25)39-5-10-13(31)14(32)17(35)21(41-10)42-18-9(4-26)40-20(36)16(34)15(18)33/h7-21,25-26,28-36H,2-5H2,1H3,(H,24,27)(H,37,38)/t7-,8+,9+,10+,11+,12+,13-,14-,15+,16+,17+,18+,19+,20?,21-,23-/m0/s1
• InChIKey: TYALNJQZQRNQNQ-UVBUFIKTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5R,6R)-5-acetamido-4-hydroxy-2-{[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,4S,5R,6R)-5-acetamido-4-hydroxy-2-{[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• Synonyms: 6′-Sialyl-D-lactose

Database IDs

• CAS Number: 56144-12-8
• MDL Number: MFCD03095515
• PubChem SID: 162249937; 24865509
• PubChem CID: 16212626

CALCULATED PROPERTIES

• Acid pKa: 2.8927894
• H Acceptors: 19
• H Donor: 13
• LogD (pH = 5.5): -9.664827
• LogD (pH = 7.4): -10.591688
• Log P: -7.105609
• Molar Refractivity: 128.608 cm^3
• Polarizability: 53.884872 Å^3
• Polar Surface Area: 335.08 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C23H39NO19

DETAILS

Sigma Aldrich - 40817

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.