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Merck
CN

A3307

Sigma-Aldrich

Sialyllactose sodium salt

~80% (HPAE/PAD), lyophilized powder, from bovine colostrum

Synonym(s):

α-NeuNAc-(2→3)- and -(2→6)-β-D-Gal-(1→4)-D-Glc, N-Acetylneuraminyl-lactose, Neuramin-lactose

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About This Item

Empirical Formula (Hill Notation):
C23H38NO19Na
CAS Number:
37449-93-7
Molecular Weight:
655.53
UNSPSC Code:
12352201
PubChem Substance ID:
24890758

Key Documents

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biological source

bovine colostrum

Assay

~80% (HPAE/PAD)

form

lyophilized powder

storage temp.

−20°C

SMILES string

[Na+].[Na+].[H][C@]1(O[C@](C[C@H](O)[C@H]1NC(C)=O)(OC[C@H]2OC(O)[C@H](O)[C@@H](O)[C@@H]2O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)C([O-])=O)[C@H](O)[C@H](O)CO.[H][C@]4(O[C@](C[C@H](O)[C@H]4NC(C)=O)(O[C@@H]5[C@@H](O)C(O)O[C@H](CO)[C@H]5O[C@@H]6O[C@H](CO)[C@H](O)[C@H](O)[C@H]6O)C([O-])=O)[C@H](O)[C@H](O)CO

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

InChI key

CFDGOUWSZLIXEU-IAQYHCRJSA-L

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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.

Other Notes

Mixture of (2→6′) and (2→3′) isomers.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

No data available

Flash Point(C)

No data available

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBF2046V
BCBC6222
1411261
092H3875
052H3886

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Ismail Hakki Ekin et al.
APMIS : acta pathologica, microbiologica, et immunologica Scandinavica, 124(12), 1093-1098 (2016-10-08)
Human and bovine group B streptococcus (GBS) isolates were serotyped and amounts of released N-acetylneuraminic acid from N-acetylneuraminyl-lactose by extracellular neuraminidase were colorimetrically assessed. According to serotyping by co-agglutination method, 30 of bovine GBS and 43 of human GBS could
Yukichi Horiguchi et al.
Biosensors & bioelectronics, 92, 234-240 (2017-02-22)
A system to discriminate human or avian influenza A remains a highly sought-after tool for prevention of influenza pandemics in humans. Selective binding of the influenza A viral hemagglutinin (HA) to specific sialic acid (SA) receptors (Neu5Acα(2-6)Gal in humans, Neu5Acα(2-3)Gal
Shun Nagamine et al.
Neuropathology : official journal of the Japanese Society of Neuropathology, 36(4), 333-345 (2015-12-22)
Glycosylation is one of the major post-translational modifications of proteins. The status of sialylation of the neuropathological hallmarks of various neurodegenerative disorders was investigated in this study. Here, we report the novel findings that two phosphorylated tau (p-tau)-containing structures associated

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