Synthesis of the Tetrasaccharide Repeating Unit from Klebsiella pneumoniae Serotype K2 Capsular Polysaccharide
Mohammad Tarique Anwar, Todd L. Lowary
TL;DR
This paper describes the synthesis of two tetrasaccharides from the K2 capsular polysaccharide of Klebsiella pneumoniae, useful for immunological and structural studies.
Contribution
A successful sequential glycosylation strategy was developed to synthesize modified tetrasaccharides with specific structural challenges.
Findings
A convergent [2 + 2] glycosylation approach failed due to C-2 inversion issues.
A sequential glycosylation method successfully produced both tetrasaccharides.
The developed route allows for the synthesis of analogs with structural modifications.
Abstract
Described is the synthesis of the two tetrasaccharides (1 and 2) related to the repeating unit from the Klebsiella pneumoniae Serotype K2 capsular polysaccharide. The compounds differ by the presence or absence of an acetate ester on O-2 of the mannopyranose residue of the repeating unit. Κey challenges in the synthesis were the installation of three 1,2-cis glycosidic linkages, including a β-mannopyranoside, the selective introduction of an α-d-glucuronic acid residue, and the late-stage incorporation of an acetate ester in 2. A convergent approach employing a key [2 + 2] glycosylation was initially explored, but the key C-2 inversion needed to install the β-mannopyranoside in the resulting tetrasaccharide failed. An alternative strategy, using a sequential glycosylation approach, was successful in providing both targets. The developed route can be adapted to provide analogs containing…
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Taxonomy
TopicsCarbohydrate Chemistry and Synthesis · Glycosylation and Glycoproteins Research · Bacteriophages and microbial interactions