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Convergent synthesis of a common pentasaccharide corresponding to the O-antigen of Escherichia coli O168 and Shigella dysenteriae type 4

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Abstract

A convenient synthetic strategy of the common acidic pentasaccharide repeating unit corresponding to the O-antigen of enterotoxigenic E. coli O168 and Shigella dysenteriae type 4 has been successfully developed. A stereoselective [2 + 3] block glycosylation method has been exploited to get the target pentasaccharide derivative. Most of the synthetic intermediates were solid and prepared in high yields from commercially available reducing sugars following a series of protection-deprotection reactions. A α-D-mannose moiety has been used as the source of α-D-glucosamine moiety. A late-stage TEMPO mediated selective oxidation reaction finally resulted in the pentasaccharide containing a glucuronic acid unit.

A convenient synthetic strategy of the common acidic pentasaccharide repeating unit corresponding to the O-antigen of enterotoxigenic E. coli O168 and Shigella dysenteriae type 4 has been successfully developed using stereoselective [2+3] block glycosylation technique.

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Acknowledgements

G. G. thanks CSIR, New Delhi for providing a Senior Research fellowship. This project was funded by the Department of Science and Technology (DST), New Delhi through Ramanna Fellowship (SR/S1/RFPC-06/2006) (A.K.M) and Bose Institute, Kolkata.

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  1. Molecular Medicine Division, Bose Institute, P-1/12, C. I. T. Scheme VII M, Kolkata, 700054, India

    Goutam Guchhait & Anup Kumar Misra

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  1. Goutam Guchhait
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Correspondence to Anup Kumar Misra.

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Guchhait, G., Misra, A.K. Convergent synthesis of a common pentasaccharide corresponding to the O-antigen of Escherichia coli O168 and Shigella dysenteriae type 4. Glycoconj J 28, 11–19 (2011). https://doi.org/10.1007/s10719-010-9317-y

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