Synthesis of the Zwitterionic Repeating Unit of the O‑Antigen from Shigella sonnei and Chain Elongation at Both Ends

Synthesis of the Zwitterionic Repeating Unit of the O‑Antigen from Shigella sonnei and Chain Elongation at Both Ends

Shigella sonnei O-antigen features a zwitterionic disaccharide repeat encompassing two rare monosaccharides. The synthesis of the AB repeat and of trisaccharides ABA′ and B′AB, which validates chain elongation at either end, is reported. All targets were synthesized using a postglycosylation oxidati...

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Bibliographic Details
Published in:Organic letters Vol. 16; no. 18; pp. 4892 - 4895
Main Authors: Pfister, Hélène B, Mulard, Laurence A
Format: Journal Article
Language:English
Published: United States American Chemical Society 19-09-2014
Subjects:
Chemical Sciences
Disaccharides - chemistry
Glucose - chemistry
Glycosylation
Molecular Structure
Monosaccharides - chemistry
O Antigens - chemistry
Organic chemistry
Shigella sonnei - immunology
Trisaccharides - chemistry
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Summary:Shigella sonnei O-antigen features a zwitterionic disaccharide repeat encompassing two rare monosaccharides. The synthesis of the AB repeat and of trisaccharides ABA′ and B′AB, which validates chain elongation at either end, is reported. All targets were synthesized using a postglycosylation oxidation strategy in combination with imidate chemistry. Precursors to residue A were obtained from l-glucose. The AAT (B) donor and acceptor were obtained from d-glucosamine. A one-step Pd(OH)2/C-mediated deprotection provided the propyl glycoside targets.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol502395k