N-glycolyl-Ganglioside GM3 Mixtu

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N-glycolyl-Ganglioside G_M3 Mixture (ammonium salt)

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Cat No: 33263

Biochemicals - Lipids

N-glycolyl-Ganglioside GM3 (NeuGc-GM3) is a form of ganglioside GM3 that contains an N-glycolylated sialic acid (NeuGc). It is not biosynthesized in humans under baseline conditions due to a mutation in CMP-Neu5Ac hydroxylase (CMAH), which converts N-...

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Territorial Availability: Available through Bertin Technologies only in France

Synonyms:

1-O-[O-[N-(hydroxyacetyl)-?-neuraminosyl]-(2?3)-O-?-D-galactopyranosyl-(1?4)-?-D-glucopyranosyl]-ceramide

Correlated keywords:

Glycolyl-neuraminyl-lactosylceramide HD3 GM HD-3 LLG1 LLG-1 NeuGcGM3 Hematoside Glycoloylganglioside Glycoloyl-GM3 GlycoloylGM3

Product Overview:
N-glycolyl-Ganglioside GM3 (NeuGc-GM3) is a form of ganglioside GM3 that contains an N-glycolylated sialic acid (NeuGc). It is not biosynthesized in humans under baseline conditions due to a mutation in CMP-Neu5Ac hydroxylase (CMAH), which converts N-acetyl sialic acid to N-glycolyl sialic acid, but NeuGc can be taken up by human cells via the diet and incorporated into glycolipids, such as ganglioside GM3.{54575,60205} NeuGc-GM3 impairs differentiation and maturation of dendritic cells in vitro and reduces CD4 expression in non-activated T cells.{54575,60206} It increases the number of lung tumor nodules formed in a murine Lewis lung carcinoma model.{60207} It is found in a variety of human cancers, including breast and lung cancers, as well as pediatric cancers.{54575} Levels of NeuGc-GM3 are negatively correlated with the number of mature dendritic cells in patient-derived non-small cell lung cancer (NSCLC) tumor tissue.{60208} Anti-NeuGc-GM3 antibodies, able to destroy tumor cells in vitro, have been found in individuals without cancer but not in patients with NSCLC.{54575,60209} N-glycolyl-Ganglioside GM3 mixture contains ganglioside GM3 molecular species with primarily C22:0, C23:0, and C24:0 fatty acyl chain lengths. [Matreya, LLC. Catalog No. 1553]

Size	500 µg
Shipping	dry ice
CAS Number	69345-49-9
Molecular Formula	C₆₄H₁₁₇N₂O₂₂ • NH₄ (for tricosanoyl)
SMILES	O[C@H]1[C@H](O[C@@H]([C@@H]([C@H]2O[C@]3(C([O-])=O)C[C@@H]([C@H]([C@]([C@@H]([C@H](O)CO)O)(O3)[H])NC(CO)=O)O)O)O[C@@H]([C@@H]2O)CO)[C@@H](CO)O[C@@H](OC[C@@H]([C@H](O)/C=C/CCCCCCCCCCCCC)NC([R])=O)[C@@H]1O.[NH4+]
Molecular Weight	1284,7
Formulation	A solid
Purity	≥98%
Custom Code	2938.90
UNSPSC code	12352100

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Our scientists are experts in the synthesis, purification, and characterization of biochemicals ranging from small drug-like heterocycles to complex biolipids, fatty acids, and many others. We are also highly skilled in all aspects of assay and antibody development, protein expression, crystallization, and structure determination.

Over the past thirty years, Cayman developed a deep knowledge base in lipid biochemistry, including research involving the arachidonic acid cascade, inositol phosphates, and cannabinoids. This knowledge enabled the production of reagents of exceptional quality for cancer, oxidative injury, epigenetics, neuroscience, inflammation, metabolism, and many additional lines of research.

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N-glycolyl-Ganglioside GM3 Mixture (ammonium salt)