Synthesis, Characterization, and Crystal Structure of Sodium (Methyl α-d-Mannopyranosid)uronate Monohydrate

Abstract

TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl)-mediated oxidation of methyl α-d-mannopyranoside with sodium hypochlorite gave sodium (methyl α-d-mannopyranosid)uronate, which was obtained as a crystalline monohydrate in ~70% yield without chromatography. Its purity was proved by NMR spectroscopy, a newly developed HPLC method, combustion analysis, and X-ray crystallography. The crystal structure, solved from synchrotron diffraction data in space group P2₁2₁2₁, revealed that the packing of the uronate molecules is connected by an extensive network of hydrogen bonds, and that the Na⁺ ion is coordinated by six oxygen ligands from one water and three surrounding sugar molecules.

Key words

mannuronic acid - oxidation - chemoselective methylation - TEMPO - HPLC

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