Neoglycolipids

Despite the small size of glycolipids, their complexity has still driven efforts for synthesis of simpler mimetics in an attempt to identify the minimal structural features required for the biological activity. To this end, many synthetic methods have been adopted in glycolipids synthesis, based on traditional glycosylation 

However, despite the evident advantages of chemoselective techniques, only a limited number of such reactions have, to the best of our knowledge, found application in the formation of the sugar-lipid bond. 

Gene therapy constitutes a novel form of drug delivery.51 To employ their full potential as therapeutic agents, genes have to be delivered in a very specific and efficient way to their cellular targets. In the field of gene therapy, the problems and high risks associated with the use of virus particles for efficient delivery of 

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M. Fukasawa, Y. Shimizu, K. Shikata, M. Nakata, R. Sakakibara, N. Yamamoto, M. Hatanaka, and T. Mizuochi, Liposome oligomannose-coated with neoglycolipid, a new candidate for a safe adjuvant for induction of CD8+ cytotoxic T lymphocytes, FEBS Lett., 441 (1998) 353-356. 

N.m.r. spectroscopy T.l.c.-m.s. analysis of oligosaccharides coupled to a lipid amine (neoglycolipids) H n.m.r. spectrum in D20 after exchange of free protons with deuterium Experiments conducted at 295 K, with acetone as the internal standard (set at 2.225 p.p.m. from 4,4-dimethyl-4-silapentane-1-sulfonate) Results compared, to within 0.005 p.p.m. (laboratory-to-la-boratory variation) of data in the literature Conformational studies by n.O.e. experiments Natural-abundance-13C analysis Chemical-shift assignment by 2D H- H and H-13C n.m.r. spectroscopy... 

The name glycolipid usually refers to the natural compounds, whereas more generally, the terms amphiphilic carbohydrate , neoglycolipid or hydropho-bized carbohydrate (H-carbohydrate) are used for synthetic unnatural structu-... 

The syntheses of natural glycolipids and neoglycolipids have been the subject of intensive research over the last ten years. Most of the papers were stimulated by the biological and physico-chemical properties of amphiphilic carbohydrates. 

The lipids used in the syntheses of neoglycolipids are often commercially available most of the long-chain carboxylic acids, n-alcanols, n-alcanethiols or -alkylamines are readily available as well as a,o)-dicarboxylic acids, diols or diamines useful for the syntheses of bola-amphiphiles. 

Duffels, A., Green, L.G., Ley, S.V. and Miller, A.D. (2000) Synthesis of high-mannose type neoglycolipids Active targeting of liposomes to macrophages in gene therapy. Chem. Eur. J., 6,1416-1430. 

Neoglycolipids for the Functionalization of Liposomes for Drug or Gene Delivery 367... 

Neoglycolipids as Probes for Investigating Biological Recognition Phenomena 369... 

Finally, an interesting example has been reported in the syntheses of new photoreactive neoglycolipid probes carrying carbohydrate determinants specific for some murine mammary adenocarcinoma cells for the study of lectin receptors on tumor cell surfaces.71... 

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