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Key Documents

A8681

Sigma-Aldrich

3′-Sialyllactose

from bovine milk or colostrum, ≥97% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C23H39NO19
CAS Number:
35890-38-1
Molecular Weight:
633.55
Beilstein:
75357
MDL number:
MFCD00166999
UNSPSC Code:
12352201
PubChem Substance ID:
24891358
NACRES:
NA.25

biological source

bovine milk or colostrum

Quality Level

200

Assay

≥97% (HPLC)

form

powder

color

white

solubility

water: 20 mg/mL, clear, colorless

cation traces

Na: 3.1-4.7%

storage temp.

−20°C

SMILES string

[Na+].[H]C(=O)[C@H](O)[C@@H](O)[C@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O[C@@]2(C[C@H](O)[C@@H](NC(C)=O)[C@@H](O2)[C@H](O)[C@H](O)CO)C([O-])=O)[C@H]1O)[C@H](O)CO

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

InChI key

LTWFUJWFLMHANB-TZCPRLTCSA-M

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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

To gain a comprehensive understanding of our extensive range of Oligosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nuria Izquierdo-Useros et al.
PLoS biology, 10(4), e1001315-e1001315 (2012-05-01)
HIV-1 is internalized into mature dendritic cells (mDCs) via an as yet undefined mechanism with subsequent transfer of stored, infectious virus to CD4+ T lymphocytes. Thus, HIV-1 subverts a DC antigen capture mechanism to promote viral spread. Here, we show
S Swaminathan et al.
Nature structural biology, 7(8), 693-699 (2000-08-10)
Clostridium botulinum neurotoxins are among the most potent toxins to humans. The crystal structures of intact C. botulinum neurotoxin type B (BoNT/B) and its complex with sialyllactose, determined at 1. 8 and 2.6 A resolution, respectively, provide insight into its
J C Wilson et al.
Bioorganic & medicinal chemistry letters, 10(24), 2791-2794 (2001-01-02)
1H NMR spectroscopy has been used to investigate the transfer of sialic acid from sialic acid donor molecules to acceptor molecules using the trans-sialidase from Typanosoma cruzi. It is clearly demonstrated that NMR spectroscopy is an efficient and powerful means
J V Mysore et al.
Gastroenterology, 117(6), 1316-1325 (1999-12-02)
Helicobacter pylori can be eradicated by administration of antimicrobials, but resistant strains have emerged, and there is a need for novel therapeutic approaches against this infection. This study aimed to determine the safety and efficacy of 3'-sialyllactose sodium salt (3'SL)
Maarten H Wilbrink et al.
Journal of agricultural and food chemistry, 63(25), 5976-5984 (2015-06-06)
Decoration of prebiotic galacto-oligosaccharides (GOS) with sialic acid yields mixtures of GOS and sialylated GOS (Sia-GOS), novel products that are expected to have both prebiotic and antiadhesive functionalities. The recombinantly produced trans-sialidase enzyme from Trypanosoma cruzi (TcTS), an enzyme with
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