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

• ChemBase ID: 131838
• 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-])O[C@H]1[C@H]([C@H](O[C@H]([C@@H]1O)O[C@H]([C@@H](CO)O)[C@@H]([C@H](C=O)O)O)CO)O)O.[Na+]
• Canonical SMILES: OC[C@H]([C@H]([C@@H]([C@H](C=O)O)O)O[C@@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)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)O.[Na+]
• InChI: InChI=1S/C23H39NO19.Na/c1-7(29)24-13-8(30)2-23(22(38)39,42-19(13)15(35)10(32)4-26)43-20-16(36)12(6-28)40-21(17(20)37)41-18(11(33)5-27)14(34)9(31)3-25;/h3,8-21,26-28,30-37H,2,4-6H2,1H3,(H,24,29)(H,38,39);/q;+1/p-1/t8-,9-,10+,11+,12+,13+,14+,15+,16-,17+,18+,19+,20-,21-,23-;/m0./s1
• InChIKey: LTWFUJWFLMHANB-TZCPRLTCSA-M

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 35890-38-1
• MDL Number: MFCD00166999
• Beilstein Number: 75357
• PubChem SID: 24891358; 162226115; 24891225
• PubChem CID: 71308479

CALCULATED PROPERTIES

• Acid pKa: 2.8378649
• H Acceptors: 19
• H Donor: 12
• LogD (pH = 5.5): -10.3492365
• LogD (pH = 7.4): -11.232414
• Log P: -7.7414303
• Molar Refractivity: 140.8673 cm^3
• Polarizability: 53.86272 Å^3
• Polar Surface Area: 345.75 Å^2
• Rotatable Bonds: 15
• 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: ≥97% (HPLC); ≥98% (HPAE/PAD)
• Biological Source: from bovine milk or colostrum

DETAILS

Sigma Aldrich - A8681

Application
3′-Sialyllactose is a compound where in 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.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A8681.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - A9079

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.