N-glycolyl-Ganglioside GM3 Mixture (ammonium salt)

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. NeuGc-GM3 impairs differentiation and maturation of dendritic cells in vitro and reduces CD4 expression in non-activated T cells. It increases the number of lung tumor nodules formed in a murine Lewis lung carcinoma model. It is found in a variety of human cancers, including breast and lung cancers, as well as pediatric cancers. 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. Anti-NeuGc-GM3 antibodies, able to destroy tumor cells in vitro, have been found in individuals without cancer but not in patients with NSCLC. N-glycolyl-Ganglioside GM3 mixture contains ganglioside GM3 molecular species with primarily C22:0, C23:0, and C24:0 fatty acyl chain lengths. As this product is derived from a natural source, there may also be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1553]Formal Name: 1-O-[O-[N-(hydroxyacetyl)-alpha-neuraminosyl]-(2->3)-O-beta-D-galactopyranosyl-(1->4)-beta-D-glucopyranosyl]-ceramide. CAS Number: 69345-49-9. Synonyms: GM3-Neugc, NeuGc-GM3, NGcGM3, N-glycolyl-GM3, N-glycolyl-Monosialoganglioside GM3, N-Glycolylneuraminyllactosylceramide. Molecular Formula: C64H117N2O22 . NH4 (for tricosanoyl). Formula Weight: 1284.7. Purity: >98%. Formulation: (Request formulation change), A solid. Solubility: Chloroform:Methanol:DI Water (2:1:0.1): soluble. 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+]. InChi Code: InChI=1S/C64H118N2O22.H3N/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-25-27-29-31-33-35-37-50(74)65-44(45(71)36-34-32-30-28-26-24-16-14-12-10-8-6-4-2)43-83-61-56(79)55(78)58(49(41-69)85-61)86-62-57(80)60(54(77)48(40-68)84-62)88-64(63(81)82)38-46(72)52(66-51(75)42-70)59(87-64)53(76)47(73)39-67,/h34,36,44-49,52-62,67-73,76-80H,3-33,35,37-43H2,1-2H3,(H,65,74)(H,66,75)(H,81,82),1H3/b36-34+,/t44-,45+,46-,47+,48+,49+,52+,53+,54-,55+,56+,57+,58+,59+,60-,61+,62-,64-,/m0./s1. InChi Key: ODSNHGRWQUWHAN-GHFHROAOSA-N.