Chemical synthesis of the repeating unit of type Ia group B Streptococcus capsular polysaccharide.

ABSTRACT: The structure of the capsular polysaccharide (CPS) of serotype Ia group B Streptococcus (GBS) has been characterized for years, but its repeating unit, which is a challenging pentasaccharide with a branch and a difficult ?-sialic acid linkage, has not been synthesized yet. In this report, an effective synthesis was developed for the serotype Ia GBS CPS repeating unit, which had a reactive functionality linked to its main-chain reducing end to enable further elaboration, such as coupling with carrier proteins. The target molecule was accomplished by a convergent [2 + 3] glycosylation strategy employing a sialo-disaccharide as donor and a branched trisaccharide as acceptor. The strategy was designed to suit the synthesis of oligomers of the repeating unit.

SUBMITTER: Mondal PK 

PROVIDER: S-EPMC4664191 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature