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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:
Molecular Weight:
633.55
Beilstein:
75357
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25

biological source

bovine milk or colostrum

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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S Crennell et al.
Nature structural biology, 7(11), 1068-1074 (2000-11-04)
Paramyxoviruses are the main cause of respiratory disease in children. One of two viral surface glycoproteins, the hemagglutinin-neuraminidase (HN), has several functions in addition to being the major surface antigen that induces neutralizing antibodies. Here we present the crystal structures
Oriane Machon et al.
Glycobiology, 27(2), 123-128 (2016-11-01)
Glycosylation is a group of post-translational modifications that displays a large variety of structures and are implicated in a plethora of biological processes. Therefore, studying glycosylation requires different technical approaches and reliable tools, lectins being part of them. Here, we
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
A Zintl et al.
Parasitology, 125(Pt 1), 45-50 (2002-08-09)
The process of host cell invasion by Babesia divergens is poorly understood and improved knowledge of the mechanism involved could lead to development of measures effective in disease prevention. The investigate parasite ligands on the erythrocyte surface, B. divergens cultures
Tadasu Urashima et al.
Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology, 146(2), 153-159 (2006-11-23)
Samples of milk from a Bryde's whale and a Sei whale contained 2.7 g/100 mL and 1.7 g/100 mL of hexose, respectively. Both contained lactose as the dominant saccharide along with small amounts of Neu5Ac(alpha2-3)Gal(beta1-4)Glc (3'-N-acetylneuraminyllactose), Neu5Ac(alpha2-6)Gal(beta1-4)Glc (6'-N-acetylneuraminyllactose) and Neu5Ac(alpha2-6)Gal(beta1-4)GlcNAc(beta1-3)Gal(beta1-4)Glc

Articles

O-Linked glycoproteins are usually large proteins with a molecular mass of >200 kDa. Glycosylation generally occurs in high-density clusters and may represent as much as 50-80% of the overall mass.

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