TY - JOUR A1 - Parameswarappa, Sharavathi G. A1 - Pereira, Claney L. A1 - Seeberger, Peter H. T1 - Synthesis of Streptococcus pneumoniae serotype 9V oligosaccharide antigens JF - Beilstein Journal of Organic Chemistry PY - 2020/// VL - 16 SP - 1693 EP - 1699 SN - 1860-5397 DO - 10.3762/bjoc.16.140 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.16.140 KW - antigen KW - carbohydrate chemistry KW - oligosaccharide KW - Streptococcus pneumoniae KW - vaccines N2 - Streptococcus pneumoniae (SP) bacteria cause serious invasive diseases. SP bacteria are covered by a capsular polysaccharide (CPS) that is a virulence factor and the basis for SP polysaccharide and glycoconjugate vaccines. The serotype 9V is part of the currently marketed conjugate vaccine and contains an acetate modification. To better understand the importance of glycan modifications in general and acetylation in particular, defined oligosaccharide antigens are needed for serological and immunological studies. Here, we demonstrate a convergent [2 + 3] synthetic strategy to prepare the pentasaccharide repeating unit of 9V with and without an acetate group at the C-6 position of mannosamine. ER -