Chemical Synthesis of the O-Antigen Repeating Unit of Escherichia coli O86 by an N-Formylmorpholine-Modulated One-Pot Glycosylation Strategy

The synthesis of the O‐antigen pentasaccharide repeating unit of the cell wall of Gram‐negative bacteria Escherichia coli O86 is reported. The synthesis features the use of an N‐formylmorpholine (NFM)‐modulated glycosylation method for the construction of 1,2‐cis α‐glycosidic linkages and an [1+1+2]...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2014-08, Vol.3 (8), p.870-876
Main Authors: Ingle, Arun B., Chao, Chin-Sheng, Hung, Wei-Cheng, Mong, Kwok-Kong Tony
Format: Article
Language:English
Subjects:
Antigens
Bacteriology
E coli
Escherichia coli
Escherichia coli O86
glycosylation
O-antigen
oligosaccharides
Organic chemistry
total synthesis
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Summary:The synthesis of the O‐antigen pentasaccharide repeating unit of the cell wall of Gram‐negative bacteria Escherichia coli O86 is reported. The synthesis features the use of an N‐formylmorpholine (NFM)‐modulated glycosylation method for the construction of 1,2‐cis α‐glycosidic linkages and an [1+1+2] iterative one‐pot α‐glycosylation strategy to accelerate the assembly of the tetrasaccharide backbone. O, I say! An N‐formylmorpholine (NFM)‐modulated one‐pot glycosylation was used for the synthesis for construction of 1,2‐cis α‐glycosidic linkages in the synthesis of the pentasaccharide repeating unit of the O‐antigen that is found in Escherichia coli O86.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201402057