Pneumococcal serotype 1 (PS1) is one of the most invasive forms of Streptococcus pneumonia. PS1 causes a host of invasive pneumococcal diseases (IPD) including pneumonia, bacteremia and meningitis. It also exhibits a high level of virulence, causing disease in patients of every age group. The antigenic component of PS1 is a polysaccharide comprised of several interesting monosaccharides including galactofuranose and 4,6-O-pyruvated galactose sugars. The former monosaccharide is unique in that it has only been found in a handful of other microbial polysaccharides and has never been found on the surface of mammalian cells. Therefore, targeting the biosynthesis of this sugar and its installation may provide researchers with a new route for the design of therapeutics targeting PS1. In this work we describes the total synthesis of a 4,6-O-pyruvated galactosyl UDP (uridine diphosphate) sugar donor to investigate PS1 biosynthesis. The 4,6-O-pyruvated galactosyl UMP (uridine monophosphate) sugar donor was synthesized in 8 steps from commercially available D-galactose with the most challenging step being the incorporation of the 4,6-O pyruvate moiety. Two additional steps were required to access final UDP donor.

Synthesis of a 4,6-O-pyruvated galactosyl donor to explore the biosynthesis of pneumococcal serotype 1 (PS1)

247th National Meeting (2014)

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