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Chemical Synthesis of the O‐Antigen Repeating Unit of Escherichia coli O86 by an N ‐Formylmorpholine‐Modulated One‐Pot Glycosylation Strategy
Author(s) -
Ingle Arun B.,
Chao ChinSheng,
Hung WeiCheng,
Mong KwokKong Tony
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201402057
Subject(s) - chemistry , glycosylation , escherichia coli , tetrasaccharide , glycosidic bond , stereochemistry , combinatorial chemistry , biochemistry , polysaccharide , enzyme , gene
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.