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NMR of Fully and Partially 13 C-Enriched Biomass Enhances Pendent Group Structural Characterization

Formally Refereed
Download (PDF 7.42 MB): https://research.fs.usda.gov/download/treesearch/80855.pdf

Abstract

Traditional solution-state NMR experiments may either fail or yield unsatisfactory results when employing fully-13C-labeled biomass due to complications arising from 13C−13C coupling. Constant-time analogs of HSQC experiments mitigate such issues and deliver enhanced sensitivity. A rarely reported CTHSQC- TOCSY experiment allows the proton coupling network to deliver much of the same value as the parent experiment on unlabeled or 10−15%-13C-labeled biomass polymers but with enhanced sensitivity. In the absence of a viable HMBC analog for long-range correlations, a relayed C−C experiment, i.e., via directly bonded 13C-labeled networks, enables the reliable assignment of coupled carbons, with the added advantage of correlating the more elusive quaternaries. A C−C-FLOPSY experiment takes advantage of fully-13C-labeled materials for mapping extensive carbon networks in the complex polymer mixtures inherent in biomass. Various pendent groups (tricin units, cis- and trans-p-coumarates, and p-hydroxybenzoates) that adorn lignins, and the cis- and trans-ferulates on arabinoxylan polysaccharides, are exquisitely revealed in spectra from isolated lignins or whole-cell-wall materials from maize, sorghum, and poplar.

Citation

Ralph, John; Lippens, Guy; Tonelli, Marco; Fry, Charles G.; Anklin, Clemens; Lu, Fachuang; Timokhin, Vitaliy I.; Nuoendagula; Smith, Rebecca A.; Liu, Sarah; Ralph, Sally A.; Lan, Wu; Tobimatsu, Yuki; Yue, Fengxia; Li, Yanding; Bunzel, Mirko; Sorieul, Mathias; Hill, Stefan; Mansfield, Shawn D.; Boerjan, Wout; Montagu, Marc Van; Rencoret, Jorge; del Río, José C.; Gao, Yu; Mortimer, Jenny C. 2026. NMR of Fully and Partially 13 C-Enriched Biomass Enhances Pendent Group Structural Characterization. Analytical Chemistry. 98(26): 19482-19492. https://doi.org/10.1021/acs.analchem.5c08043.
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