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Pavashe P, Elamparuthi E, Hettrich C, et al. Synthesis of 2-Thiocarbohydrates and Their Binding to Concanavalin A. J Org Chem. 2016;81(18):8595-603doi: 10.1021/acs.joc.6b00987.
Pavashe, P., Elamparuthi, E., Hettrich, C., Möller, H. M., & Linker, T. (2016). Synthesis of 2-Thiocarbohydrates and Their Binding to Concanavalin A. The Journal of organic chemistry, 81(18), 8595-603. https://doi.org/10.1021/acs.joc.6b00987
Pavashe, Prashant, et al. "Synthesis of 2-Thiocarbohydrates and Their Binding to Concanavalin A." The Journal of organic chemistry vol. 81,18 (2016): 8595-603. doi: https://doi.org/10.1021/acs.joc.6b00987
Pavashe P, Elamparuthi E, Hettrich C, Möller HM, Linker T. Synthesis of 2-Thiocarbohydrates and Their Binding to Concanavalin A. J Org Chem. 2016 Sep 16;81(18):8595-603. doi: 10.1021/acs.joc.6b00987. Epub 2016 Aug 30. PMID: 27518032.
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J Org Chem. 2016 Sep 16;81(18):8595-603. doi: 10.1021/acs.joc.6b00987. Epub 2016 Aug 30.

Synthesis of 2-Thiocarbohydrates and Their Binding to Concanavalin A.

The Journal of organic chemistry

Prashant Pavashe, Elangovan Elamparuthi, Cornelia Hettrich, Heiko M Möller, Torsten Linker

Affiliations

  1. Department of Chemistry, University of Potsdam , Karl-Liebknecht-Str. 24-25, 14476 Potsdam, Germany.

PMID: 27518032 DOI: 10.1021/acs.joc.6b00987

Abstract

A convenient and general synthesis of 2-thiocarbohydrates via cerium ammonium nitrate oxidation of the thiocyanate ion is described. Radical addition to glycals proceeds with excellent regio- and good stereoselectivities in only one step, deprotection affords water-soluble 2-thio saccharides. Binding studies to Con A have been performed by isothermal titration calorimetry (ITC) and saturation transfer difference (STD) NMR spectroscopy. The 2-thiomannose derivative binds even stronger to Con A than the natural substrate, offering opportunities for new lectin or enzyme inhibitors.

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