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Synthesis of 6-Mercaptohexanoylhydrazones of Mono- and Disaccharides as a Potential Glycoligands of Noble Metal Glyconanoparticles

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Abstract

The 1H and 13C NMR spectroscopy was used to study the structure of previously unknown aldose series condensation products (L-fucose, L-rhamnose, D-mannose, D-galactose, D-glucose, N-acetyl-D-glucosamine, N-acetyl-D-mannosamine, D-lactose and D-maltose) with 6-mercapto­hexanoic acid hydrazide—promising glycoligands of noble metal nanoparticles. It was shown that L-fucose, L-rhamnose, D-mannose, D-galactose and N-acetyl-D-mannosamine derivatives exist in solution in DMSO-d6 as a tautomeric mixture of open hydrazone and cyclic pyranose forms. The linear hydrazone form is represented by a set of Z′,E′-conformational isomers, which differ in the arrangement of substituents relative to the C–N amide bond in comparable amounts. The condensation products obtained on the basis of D-glucose, N-acetyl-D-glucosamine, D-lactose and D-maltose in the crystalline state and in solutions in DMSO-d6 have an exclusively cyclic pyranose structure represented by α,β-configurational isomers. A similar transition to the pyranose form is observed in solutions of all the studied compounds in D2O.

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Authors and Affiliations

  1. Institute of Macromolecular Compounds of the Russian Academy of Sciences, 199004, St. Petersburg, Russia

    A. Yu. Еrshov, А. А. Маrtynenkov & А. V. Yakimansky

  2. State Research Testing Institute of Military Medicine, Ministry of Defense of the Russian Federation, 195043, St. Petersburg, Russia

    I. V. Lagoda

  3. St. Petersburg State University, 199034, St. Petersburg, Russia

    А. V. Yakimansky

Authors
  1. A. Yu. Еrshov
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  2. А. А. Маrtynenkov
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  3. I. V. Lagoda
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  4. А. V. Yakimansky
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Correspondence to A. Yu. Еrshov.

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Еrshov, A.Y., Маrtynenkov, А.А., Lagoda, I.V. et al. Synthesis of 6-Mercaptohexanoylhydrazones of Mono- and Disaccharides as a Potential Glycoligands of Noble Metal Glyconanoparticles. Russ J Gen Chem 90, 1863–1868 (2020). https://doi.org/10.1134/S1070363220100084

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