Conformational Restriction of Sphingolipids

Kolter T (2004) Conformational restriction of sphingolipids. In Schmuck C, Wennemers H (eds) Highlights in bioorganic chemistry methods and applications. Wiley-VCH, Weinheim, p 48... 

Conformational restriction of biologically flexible molecules is a successful strategy in drug development. Application of this concept to ceramide, the membrane anchor of sphingolipids, led to the unexpected inhibition of glycosyltransferases involved in the combinatorial biosynthesis of gangliosides. This discovery offers a new approach to cell surface engineering. 

With the exception of sterols most membrane lipids are conformationally flexible molecules. The question arises whether the concept of conformational restriction can be extended from peptides to the field of sphingolipids. The observation that conformationally restricted derivatives of myristic acid have selective toxicity towards trypanosomes demonstrates that this strategy is also applicable... 

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