Glycerol-based compounds acyl glycerols

The lipids described in sections 6.2.2 and 6.2.3 were based on a glycerol backbone. However, another important group of acyl lipids have sphingosine-based structures. Both glycolipids and phospholipids are found, with some compounds capable of dual classification, i.e. phospholipids which contain sugar residues. 

In addition to kinetic resolution processes, the previously described peptide-catalysed acylation reaction of alcohols can be applied to desymmetrisation of meso compounds. In 2005, Miller and coworkers published the desymmetrisation of prochiral glycerol derivatives via enantioselective acylation of one primaiy alcohol function. A (3-tum histidine-based pentapeptide was identified as the most promising catalyst from a peptide libraiy and afforded the monoacylated product with up to 97% enantiomeric excess. One year later Miller and Hansen successfully demonstrated the desymmetrisation of a meso bis-phenol compound, which was found to be challenging because of the large distance between the two OH groups as well as between the desired site of functionalisation and the prochiral stereogenic centre of the substrate. The nucleophilic N-methylhistidine containing peptide 9 was identified as a powerful tool for monoacylation via extensive libraiy... 

Phosphatides are derivatives of phosphatidyl residues, which are based on 1,2-diacyl-sn-glycerol, which contains bound phosphoric acid on the C-3 hydroxyl. The basic compound is 3-sn-phosphatidic acid (l,2-diacyl-sn-glycerol3-phosphoricacid) (3-53). If only position C-1 (which is more often than position C-2) is occupied by an acyl, the resulting residue derived from l-acyl-s -glycerol is caUed lysophosphatidyl. The corresponding acid is 3-s -lysophosphatidic acid (l-acyl-s -glycerol3-phosphoric acid) (3-54). 

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