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Homo- and Hetero-Nuclear 2d nMr Techniques: Umambiguous Structural Probes for Non-Cyclic Benzyl Aryl Ethers in Soluble Lignin Samples

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A number of two-dimensional NMR experiments are evaluated with respect to their ability to provide unambiguous evidence for the presence or absence of non-cyclic benzyl aryl ether (α-O-4) structures in soluble lignin samples. The most suitable techniques, in terms of both sensitivity and structural information content were the homonuclear Hartmann-Hahn (HOHAHA) and heteronuclear multiple quantum coherence (HMQC) techniques. By spiking an acetylated Pinus radiata MWL sample with an oligomeric α-0-4 ether model compound, it was possible to determine a detection limit of <0.3 structures per 100 lignin C9 units for both the HOHAHA and HMQC techniques. From this, and other work, it can be shown that if α-O-4 structures are present in MWL samples, they are present at a level below the detection limit of these experiments. The implications of these results are discussed in terms of lignin biosynthesis and reactivity.

Affiliations: 1: Department of Chemistry, The University of Waikato, Private Bag 3105, Hamilton, New Zealand; 2: Institute of Biotechnology, P.O. Box 45, FIN-00014 University of Helsinki, Finland


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