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Merck

A8681

3′-Sialyllactose

from bovine milk or colostrum, ≥95% (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
UNSPSC Code:
12352201
NACRES:
NA.25
PubChem Substance ID:
24891358
MDL number:
MFCD00166999
Beilstein/REAXYS Number:
75357

Key Documents

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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

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 key

LTWFUJWFLMHANB-TZCPRLTCSA-M

biological source

bovine milk or colostrum

form

powder

color

white

solubility

water: 20 mg/mL, clear, colorless

cation traces

Na: 3.1-4.7%

storage temp.

−20°C

Quality Level

200

assay

≥95% (HPLC)

Related Categories

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SLBZ2298
SLBX4359
SLBV2319
SLBT8124
SLBM8426V

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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
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
T Nakamura et al.
Carbohydrate research, 329(2), 471-476 (2000-12-16)
The composition of the products formed by treatment of commercial alpha-Neu5Ac-(2 --> 3)-beta-D-Galp-(1 --> 4)-D-Glc (3'-sialyllactose) with glacial acetic acid was investigated by 1H-13C one- and two-dimensional NMR spectroscopy and fast atom bombardment-mass spectrometry. The data confirmed that the major
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