Biology; Chemistry and chemical biology; Chemical and biological engineering; Biomedical engineering
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Synthesis of a Versatile Neuraminic Acid C-Disaccharideas Precursor for the Synthesis of C-Glycoside Analogs of GangliosidesH.G. Bazin, Y. Du, T. Polat, R.J. Linhardt, Journal of Organic Chemistry,64,7254-7259, 1999.
Gangliosides are cell-surface sialic acid containing glycolipids. They are found in high concentration on the surface of central nervous system cells. Gangliosides are believed to play a role in important biological events such as cell growth regulation, cell−cell adhesion, and malignancy. 1-3 GM4 (1, Scheme 1) is structurally the simplest ganglioside and has been isolated as a minor component from brain, rat kidney, mouse erythrocytes, and chicken egg yolk. 4-6 GM4 is an important cell adhesion molecule in cell growth and tissue regeneration and promotes neuron adhesion through its interaction with myelin-associated glycoprotein. 7 GM3 (2, Scheme 1) was first isolated from equine erythrocytes 8 and is known to modulate the epidermal growth factor (EGF) and the platelet-derived growth factor (PDGF) receptors. 9,10 Tumors, such as those involved in brain cancer, overexpress EGF receptor. GM4 and GM3 are also found in high concentration in tumor cells. 11;
Journal of Organic Chemistry, 64, 7254-7259; Note : if this item contains full text it may be a preprint, author manuscript, or a Gold OA copy that permits redistribution with a license such as CC BY. The final version is available through the publisher’s platform.
The Linhardt Research Labs.; The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS);
The Linhardt Research Labs Online Collection; Rensselaer Polytechnic Institute, Troy, NY; https://harc.rpi.edu/;