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Expedient synthesis of the pentasaccharide repeating unit of the O-antigen of Escherichia coli O86 and its conformational analysis

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Abstract

Synthesis of the pentasaccharide with a 2-aminoethyl linker attached to the reducing end corresponding to the cell wall O-antigen of Escherichia coli O86 strain is reported. The synthetic strategy involves sequential glycosylation of suitably protected monosaccharide intermediates under similar glycosylation reaction conditions. Thioglycosides have been used as glycosyl donor throughout the synthetic strategy. Conformational analysis of the synthesized pentasaccharide has been carried out using 2D ROESY NMR spectral analysis and all atom explicit molecular dynamics (MD) simulation technique.

Facile synthesis of the pentasaccharide with a 2-aminoethyl linker attached to the reducing end corresponding to the cell wall O-antigen of Escherichia coli O86 strain is reported. Conformational analysis of the synthesized pentasaccharide has been carried out using 2D ROESY NMR spectral analysis and all atom explicit molecular dynamics (MD) simulation technique.

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Acknowledgments

I. B. and R. K. K. thank CSIR, India for providing Senior Research Fellowships respectively. This work was supported by SERB, New Delhi, India (AKM) [Project No. EMR/2015/000282]. The authors sincerely thank reviewers for their valuable comments to improve the quality of the manuscript.

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Authors and Affiliations

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

    Ishani Bhaumik & Anup Kumar Misra

  2. Department of Biophysics, Bose Institute, P-1/12, C.I.T. Scheme VII M, Kolkata, 700054, India

    Rajiv Kumar Kar & Anirban Bhunia

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  1. Ishani Bhaumik
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  2. Rajiv Kumar Kar
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Correspondence to Anup Kumar Misra.

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Bhaumik, I., Kar, R.K., Bhunia, A. et al. Expedient synthesis of the pentasaccharide repeating unit of the O-antigen of Escherichia coli O86 and its conformational analysis. Glycoconj J 33, 887–896 (2016). https://doi.org/10.1007/s10719-016-9687-x

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  • DOI: https://doi.org/10.1007/s10719-016-9687-x

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