disodium (2R,4S,5R,6R)-2-{[(3R,4R,5R,6R)-2,3-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate (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: 133662
• Molecular Formular: C46H76N2Na2O38
• Molecular Mass: 1311.06578
• Monoisotopic Mass: 1310.38714456
• 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.CC(=O)N[C@@H]1[C@H](C[C@](O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)[O-])O[C@H]1[C@@H]([C@H](OC([C@@H]1O)O)CO)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)O.[Na+].[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.OC[C@H]1OC(O)[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O)O[C@]1(C[C@H](O)[C@H]([C@@H](O1)[C@@H]([C@@H](CO)O)O)NC(=O)C)C(=O)[O-])O.[Na+].[Na+]
• InChI: InChI=1S/2C23H39NO19.2Na/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;1-6(28)24-11-7(29)2-23(22(37)38,42-18(11)12(31)8(30)3-25)43-19-16(35)20(36)39-10(5-27)17(19)41-21-15(34)14(33)13(32)9(4-26)40-21;;/h7-21,25-26,28-36H,2-5H2,1H3,(H,24,27)(H,37,38);7-21,25-27,29-36H,2-5H2,1H3,(H,24,28)(H,37,38);;/q;;2*+1/p-2/t7-,8+,9+,10+,11+,12+,13-,14-,15+,16+,17+,18+,19+,20?,21-,23-;7-,8+,9+,10+,11+,12+,13-,14-,15+,16+,17+,18+,19+,20?,21-,23+;;/m00../s1
• InChIKey: CFDGOUWSZLIXEU-IAQYHCRJSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (2R,4S,5R,6R)-2-{[(3R,4R,5R,6R)-2,3-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate (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: disodium (2R,4S,5R,6R)-2-{[(3R,4R,5R,6R)-2,3-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate (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→3)- and -(2→6)-β-D-Gal-(1→4)-D-Glc; N-Acetylneuraminyl-lactose; Neuramin-lactose; Sialyllactose sodium salt

Database IDs

• CAS Number: 37449-93-7(freeacid)
• PubChem SID: 24890758; 162227939
• PubChem CID: 16218893

CALCULATED PROPERTIES

• Rotatable Bonds: 22
• Lipinski's Rule of Five: false
• 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

PROPERTIES

Physical Property

• Apperance: lyophilized powder

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: ~80% (HPAE/PAD)
• Biological Source: from bovine colostrum

DETAILS

Sigma Aldrich - A3307

Other Notes
Mixture of (2→6′) and (2→3′) isomers.
Application
3′-Sialyllactose is a compound wherein the acetylneuraminyl (NANA) unit is connected to the galactosyl unit of lactose at the 3 position. In 6’-sialylactose, this connection is at the 6 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.