N-omega-CD3-Octadecanoyl monosialoganglioside GM1

Application Notes:

Gangliosides1 are acidic glycosphingolipids that form lipid rafts in the outer leaflet of the cell plasma membrane, especially in neuronal cells in the central nervous system.2 They participate in cellular proliferation, differentiation, adhesion, signal transduction, cell-to-cell interactions, tumorigenesis, and metastasis.3 The accumulation of gangliosides has been linked to several diseases including Tay-Sachs and Sandhoff disease while an autoimmune response against gangliosides can lead to Guillain-Barre syndrome. GM1 stimulates neuronal sprouting and enhances the action of nerve growth factor (NGF) by directly and tightly associating with Trk, the high-affinity tyrosine kinase-type receptor for NGF. It is the specific cell surface receptor for cholera toxin.4 This deuterated ganglioside is ideal for the identification of gangliosides in samples and biological systems using mass spectrometry or HPLC.5

References: 
1. L. Svennerholm, et al. (eds.), Structure and Function of Gangliosides, New York, Plenum, 1980 
2. T. Kolter, R. Proia, K. Sandhoff, Combinatorial Ganglioside Biosynthesis. J. Biol. Chem., July Vol. 277, No. 29, pp. 25859-25862, 2002 
3. S. Birkle, G. Zeng, L. Gao, R. K. Yu, and J. Aubry. Role of tumor-associated gangliosides in cancer progression. Biochimie, 85, 455–463, 2003 
4. C. E. Miller, J. Majewski, R. Faller, S. Satija, and T. L. Kuhl, Cholera Toxin Assault on Lipid Monolayers Containing Ganglioside GM1. Biophysj., June Vol. 86(6), 3700–3708, 2004 
5. J. Gu, C. Tifft and S. Soldin “Simultaneous quantification of GM1 and GM2 gangliosides by isotope dilution tandem mass spectrometry” Clinical Biochemistry, Vol. 41(6) pp. 413-417, 2008