An abundant oligosaccharide in milk
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3'-Sialyllactose (sodium salt)

Item No. 16617

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
O-(N-acetyl-α-neuraminosyl)-(2→3)-O-β-D-galactopyranosyl-(1→4)-D-glucose, monosodium salt
CAS Number
128596-80-5
Synonyms
  • 3'-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@@]2(C([O-])=O)O[C@]([C@H](O)[C@H](O)CO)([H])C(NC(C)=O)[C@@H](O)C2)[C@@H](O)[C@H](O[C@@]([C@H](O)CO)([H])[C@H](O)[C@@H](O)C([H])=O)O[C@@H]1CO.[Na+]
InChi Code
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
InChi Key
LTWFUJWFLMHANB-YZMHZYKKSA-M
Origin
Animal/Bovine lactose
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    3'-Sialyllactose consists of the monosaccharide N-acetylneuraminic acid linked to the galactosyl subunit of lactose at the 3 position. It is an abundant oligosaccharide in the milk of many mammals, including cows and humans, particularly postpartum.1,2 3'-Sialyllactose avidly binds several viral strains, including strains of influenza, HIV-1, reovirus, and polyomavirus.3,4,5,6 In some cases, binding of 3’-sialyllactose to viral proteins alters viral infectivity.3,4,5 3'-Sialyllactose also alters Helicobacter activity and impacts bacterial colonization of gut.7,8

    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. 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).

    4. 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).

    5. 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).

    6. 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).

    7. Simon, P.M., Goode, P.L., Mobasseri, A., et al. Inhibition of Helicobacter pylori binding to gastrointestinal epithelial cells by sialic acid-containing oligosaccharides. Infect. Immun. 65(2), 750-757 (1997).

    8. Weiss, G.A., and Hennet, T. The role of milk sialyllactose in intestinal bacterial colonization. Adv. Nutr. 3(3), 483S-488S (2012).