Synthesis of 6-Mercaptohexanoylhydrazones of Mono- and Disaccharides as a Potential Glycoligands of Noble Metal Glyconan
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hesis of 6-Mercaptohexanoylhydrazones of Mono- and Disaccharides as a Potential Glycoligands of Noble Metal Glyconanoparticles A. Yu. Еrshova,*, А. А. Маrtynenkova, I. V. Lagodab, and А. V. Yakimanskya,c a
Institute of Macromolecular Compounds of the Russian Academy of Sciences, St. Petersburg, 199004 Russia b State Research Testing Institute of Military Medicine, Ministry of Defense of the Russian Federation, St. Petersburg, 195043 Russia c St. Petersburg State University, St. Petersburg, 199034 Russia *e-mail: [email protected] Received June 22, 2020; revised June 22, 2020; accepted July 9, 2020
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. Keywords: thiol-containing mono- and disaccharides, ring-chain tautomerism
DOI: 10.1134/S1070363220100084 Thiolated sugar are an intensively developing class of carbohydrates that have recently found application as ligands in the synthesis of noble metal glyconanoparticles. Due to the branched network of carbohydrate fragments, glyconanoparticles imitate the natural cell surface and have a high affinity for natural glycoprotein molecules (lectins), and the presence of a metal core in their composition gives them unique optical properties [1–14]. Indeed, Ag and Au glyconanoparticles are used as immunochemical markers and biosensors [3–5], are actively used in the diagnosis and treatment of oncological diseases [1, 6–13], and have bactericidal and antiviral properties [14]. Previously, we have proposed a simple method for the synthesis of Ag and Au glyconanoparticles based on the condensation products of thioglycolic, 3-mercaptopropionic, and 2-mercaptobenzoic acid hydrazides with a series of mono- and disaccharides, and also have demonstrated a high antiviral and antimicrobial activity of the resulting conjugates [15–20]. Developing the
“hydrazide technology” for the synthesis of thiolated sugars and glyconanoparticles of noble metals on their basis, we studied the possibilities of obtaining thiolated glycoligands using the example of the condens
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