Synthesis and Characterization of Periodate-Oxidized Polysaccharides: Dialdehyde Xylan (DAX)
2016
Amer, Hassan | Nypelö, Tiina | Sulaeva, Irina | Bacher, Markus | Henniges, Ute | Potthast, Antje | Rosenau, Thomas
The cleavage of the C2–C3 bond in the building units of 1 → 4-linked polysaccharides by periodate formally results in two aldehyde units, which are present in several masked forms. The structural elucidation of such polysaccharide dialdehydes remains a big challenge. Since polysaccharide derivatives are increasingly applied in materials technology, unveiling the exact structure is of utmost importance. To address this issue for xylan, dialdehyde xylan (DAX, oxidation degree of 91.5%) has been synthesized as water-soluble polymer. The ATR-FTIR spectrum of DAX showed free aldehyde to be absent and exhibited a characteristic absorption at 858 cm⁻¹ related to hemiacetal groups. By a combination of 1D and 2D NMR techniques, it was confirmed that oxidized xylan is present as poly(2,6-dihydroxy-3-methoxy-5-methyl-3,5-diyl-1,4-dioxane). Based on GPC analysis, the DAX polymer shows a slightly lower molar mass (6.6 kDa) compared to the starting material (7.7 kDa) right after oxidation, and degraded further after one month of storage in 0.1 M NaCl solution (4.3 kDa). The oxidized xylan demonstrated lower thermal stability upon TGA analysis and a greater amount of residual char (20.6%) compared to the unmodified xylan (13.7%).
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