A major milk oligosaccharide
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6'-Sialyllactose (sodium salt)

Item No. 17866

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
O-(N-acetyl-α-neuraminosyl)-(2→6)-O-β-D-galactopyranosyl-(1→4)-D-glucose, monosodium salt
CAS Number
157574-76-0
Synonyms
  • 6'-N-Acetylneuraminyl-D-lactose
Molecular Formula
C23H38NO19 • Na
Formula Weight
655.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 5 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO[C@@]2(C([O-])=O)O[C@]([C@@H]([C@H](O)CO)O)([H])[C@H](NC(C)=O)[C@@H](O)C2)O[C@H]1O[C@@]([C@H](O)CO)([H])[C@H](O)[C@@H](O)C=O.[Na+]
InChi Code
InChI=1S/C23H39NO19.Na/c1-7(28)24-13-8(29)2-23(22(38)39,43-20(13)15(34)10(31)4-26)40-6-12-16(35)17(36)18(37)21(41-12)42-19(11(32)5-27)14(33)9(30)3-25;/h3,8-21,26-27,29-37H,2,4-6H2,1H3,(H,24,28)(H,38,39);/q;+1/p-1/t8-,9-,10+,11+,12+,13+,14+,15+,16-,17
InChi Key
LJNVKOGOHXWREM-MZZLGFSDSA-M
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    6'-Sialyllactose consists of the monosaccharide N-acetylneuraminic acid (Item No. 16091) linked to the galactosyl subunit of lactose at the 6 position. This connection is at the 3 position in the related compound, 3’-sialyllactose (Item No. 16617). Both are major milk oligosaccharides that avidly bind several viral strains, including strains of influenza, HIV-1, reovirus, and polyomavirus.1,2,3,4,5,6 These compounds can be used to differentiate and characterize the binding domains of viruses that recognize N-acetylneuraminic acid-capped cell surface receptors. They are also used as analytical reference standards for quantification in samples such as milk or colostrum.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Duncan, P.I., Raymond, F., Fuerholz, A., et al. Sialic acid utilisation and synthesis in the neonatal rat revisited. PLoS One 4(12), 1-10 (2009).

    2. Sprenger, N., and Duncan, P.I. Sialic acid utilization. Adv. Nutr. 3(3), 392S-397S (2012).

    3. Iskarpatyoti, J.A., Morse, E.A., McClung, R.P., et al. Serotype-specific differences in inhibition of reovirus infectivity by human-milk glycans are determined by viral attachment protein σ1. Virology 433(2), 489-497 (2012).

    4. Neu, U., Khan, Z.M., Schuch, B., et al. Structures of B-lymphotropic polyomavirus VP1 in complex with oligosaccharide ligands. PLoS Pathog. 9(10), 1-10 (2013).

    5. Rosa Borges, A., Wieczorek, L., Johnson, B., et al. Multivalent dendrimeric compounds containing carbohydrates expressed on immune cells inhibit infection by primary isolates of HIV-1. Virology 408(1), 80-88 (2010).

    6. Wu, W., and Air, G.M. Binding of influenza viruses to sialic acids: Reassortant viruses with A/NWS/33 hemagglutinin bind to α2,8-linked sialic acid. Virology 325(2), 340-350 (2004).