Glycosphingolipids and sphingolipids of medical interest

I have already shown several syntheses of sphingolipids as microbial metabolites or marine natural products. Sphingolipids are building blocks of the plasma membrane of eukaryotic cells. Their function is to anchor lipid-bound carbohydrates to cell surfaces, and to construct the epidermal water permeability barrier. The chemistry of sphingolipids is therefore closely related to dermatology or the science of skin. This section first treats sphingolipid in human epidermis. 

There are a number of reviews on sphingolipids. Biological and medical aspects of sphingolipid chemistry were reviewed by Kolter and Sandhoff.31 Bio-organic chemistry of ceramide was reviewed by Kolter and coworkers.32 Chemical aspects of sphingolipid research were also reviewed.33,34 

162 was also proposed by Downing and coworkers for the cerebroside which they isolated from pig epidermis. The esterified cerebroside 162 works as a functional water barrier in the skin. 

162 as a waxy solid melting at 122-125 °C. Its -NMR spectrum was identical with that of the natural product, and therefore the structure 162 of type I epidermoside was confirmed. 

Chemical Synthesis of Hormones, Pheromones and Other Bioregulators 

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