6'-N-Acetylneuramin-lactose sodium salt

Product Name6'-N-Acetylneuramin-lactose sodium salt
CAS157574-76-0
MFC23H40NNaO19
MW657.55
EINECS
MOL File157574-76-0.mol

Chemical Properties

Melting point	177-179°C
storage temp.	Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility	DMSO (Slightly, Heated), Methanol (Slightly), Water (Sparingly)
form	Solid
color	White to Off-White
Stability	Hygroscopic
InChIKey	WNDREJAZQDPQFB-LTDHETQONA-N
SMILES	[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

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

6''-Sialyllactose consists of the monosaccharide N-acetylneuraminic acid linked to the galactosyl subunit of lactose at the 6 position. This connection is at the 3 position in the related compound, 3’-sialyllactose . Both are major milk oligosaccharides that avidly bind several viral strains, including strains of influenza, HIV-1, reovirus, and polyomavirus. These compounds can be used to differentiate and characterize the binding domains of viruses that recognize N-acetylneuraminic acid-capped cell surface receptors. They are also used as analytical reference standards for quantification in samples such as milk or colostrum.

Uses

6''-Sialyllactose binds several viral strains, including strains of influenza, HIV-1, reovirus, and polyomavirus.

References

[1] PETER I DUNCAN. Sialic acid utilisation and synthesis in the neonatal rat revisited.[J]. PLoS ONE, 2009, 4 12: e8241. DOI: 10.1371/journal.pone.0008241
[2] NORBERT SPRENGER Peter I D. Sialic Acid Utilization[J]. Advances in Nutrition, 2012, 3 3: Pages 392S-397S. DOI: 10.3945/an.111.001479
[3] JASON A. ISKARPATYOTI . Serotype-specific differences in inhibition of reovirus infectivity by human-milk glycans are determined by viral attachment protein σ1[J]. Virology, 2012, 433 2: Pages 489-497. DOI: 10.1016/j.virol.2012.08.036
[4] URSULA NEU. Structures of B-lymphotropic polyomavirus VP1 in complex with oligosaccharide ligands.[J]. PLoS Pathogens, 2013: e1003714. DOI: 10.1371/journal.ppat.1003714
[5] ANDREW ROSA BORGES . Multivalent dendrimeric compounds containing carbohydrates expressed on immune cells inhibit infection by primary isolates of HIV-1[J]. Virology, 2010, 408 1: Pages 80-88. DOI: 10.1016/j.virol.2010.09.004
[6] WENXIN WU Gillian M A. Binding of influenza viruses to sialic acids: reassortant viruses with A/NWS/33 hemagglutinin bind to α2,8-linked sialic acid[J]. Virology, 2004, 325 2: Pages 340-350. DOI: 10.1016/j.virol.2004.05.013

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