First Synthesis of Bacillus cereus Ch HF-PS Cell Wall Trisaccharide Repeating Unit

The first total synthesis of Ch HF-PS, a cell wall trisaccharide repeating unit of B. cereus, is reported. The synthetic trisaccharide is appended with an aminopropyl linker at the reducing end to allow for conjugation to proteins and microarrays. The convergent synthesis involves transformation of...

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Bibliographic Details
Published in:Organic letters 2014-08, Vol.16 (16), p.4336-4339
Main Authors: Podilapu, Ananda Rao, Kulkarni, Suvarn S
Format: Article
Language:English
Subjects:
Bacillus cereus - chemistry
Carbohydrate Sequence
Cell Wall - chemistry
Glycosylation
Mannose - chemistry
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Polysaccharides, Bacterial - chemical synthesis
Polysaccharides, Bacterial - chemistry
Trisaccharides - chemical synthesis
Trisaccharides - chemistry
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Summary:The first total synthesis of Ch HF-PS, a cell wall trisaccharide repeating unit of B. cereus, is reported. The synthetic trisaccharide is appended with an aminopropyl linker at the reducing end to allow for conjugation to proteins and microarrays. The convergent synthesis involves transformation of d-mannose into an orthogonally protected rare AAT sugar building block, two consecutive α-stereoselective glycosylations, β-selective attachment of the linker by solvent participation, and amide bond formation, as key steps.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol5021527