Convergent Synthesis of the Pentasaccharide Repeating Unit of the O-Antigen of Escherichia coli O36

Pintu Kumar Mandal

doi:10.1055/s-0034-1379952

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(06): 836-844
DOI: 10.1055/s-0034-1379952

paper

Convergent Synthesis of the Pentasaccharide Repeating Unit of the O-Antigen of Escherichia coli O36

Pintu Kumar Mandal*

Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram extension, Sitapur Road, Lucknow, 226 031, India eMail: pintuchem06@gmail.com

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Abstract

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Abstract

An efficient synthesis of the pentasaccharide repeating unit of the O-antigen of Escherichia coli O36 is reported. A stereoselective [2 + 3] block glycosylation method has been exploited to obtain the target pentasaccharide derivative using thioglycoside, trichloroacetimidate, and halide-exchange glycosylation procedures. The 2-azidoethyl group has been used as the anomeric protecting group to make the glycone moiety with a readily available linker for its conjugation to a protein without destroying the cyclic structure at the reducing end. Yields were high in all the intermediate steps.

Key words

Escherichia coli - pentasaccharide - glycosylation - lipopolysaccharide - O-antigen

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Referenzen

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