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There is a growing consciousness that the observed liquid crystallinity of many biological materials be related with their biological functions. While the survival of living systems depends on the flexibility and reformability of structures, the combination of softness and structure of the liquid crystalline state seems to determine the functionality of biological materials. The richest sources of liquid crystals derived from living systems are found in cell membranes, and glycolipids, which are important components of cell membranes, show fascinating self-assembling behaviour. In this chapter, by examining typical examples of liquid crystalline glycolipids with respect to their chemical structure, we will illustrate our understanding of the self-assembling and self-organising properties of glycolipids to the point of predictivity for rational design of mesomorphism in such systems.

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