Synthetic GPIs

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Science  20 Aug 2004:
Vol. 305, Issue 5687, pp. 1079
DOI: 10.1126/science.305.5687.1079b

An effective malaria vaccine could potentially save millions of lives each year but is not yet available. Conjugated carbohydrates that mimic the structures of surfaced-exposed moieties such as glycosylphosphatidylinositol (GPI) would be useful for vaccine development (see also Verez-Bencomo et al., Reports, 23 July, p. 522). Seeberger et al. report a synthesis strategy for two such conjugates that resemble the structure of a malarial GPI toxin. Compared to their earlier synthesis of one of the compounds by automated assembly, the new solution-phase synthesis is slower but can be scaled up more easily. It may thus provide access to large enough quantities for preclinical and clinical trials. The GPI toxin is a hexasaccharide with fatty acid chains attached in two places, but the exact nature of these lipid chains is not known. In a related paper, Liu and Seeberger report a synthesis route that allows lipid chains to be attached to a disaccharide subunit using a protection group strategy that involves substituted benzyl ethers and may also be applied to the synthesis of other complex molecules. — JFU

Chem. Commun. 2004, 1706; 1708 (2004).

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