Ultra-high-performance supercritical fluid chromatography with quadrupole-time-of-flight mass spectrometry (UHPSFC/QTOF-MS) for analysis of lignin-derived monomeric compounds in processed lignin samples

Prothmann, Jens; Sun, Mingzhe; Sartipy, Peter; Sandahl, Margareta; Turner, Charlotta

doi:10.1007/s00216-017-0663-5

Cited by 45 publications

(51 citation statements)

References 28 publications

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“…Depending on both the origin of lignin, its mode of separation and the method of depolymerization, a very different distribution between the formed low molecular weight compounds can be obtained. Previously identified compounds in the depolymerized softwood lignin samples using the depolymerization method employed here, have been 4-HBA, vanillate, vanillin and guaiacol [38]. Similar compounds were also reported in other related substrates (Table 3).…”

Section: Discussionsupporting

confidence: 77%

RETRACTED ARTICLE: Bacterial conversion of depolymerized Kraft lignin

Ravi

Abdelaziz

Nöbel

et al. 2018

Biotechnol Biofuels

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BackgroundLignin is a potential feedstock for microbial conversion into various chemicals. However, the degradation rate of native or technical lignin is low, and depolymerization is needed to obtain reasonable conversion rates. In the current study, base-catalyzed depolymerization—using NaOH (5 wt%)—of softwood Kraft lignin was conducted in a continuous-flow reactor system at temperatures in the range 190–240 °C and residence times of 1 or 2 min. The ability of growth of nine bacterial strains belonging to the genera Pseudomonas and Rhodococcus was tested using the alkaline-treated lignin as a sole carbon source.ResultsPseudomonas fluorescens and Rhodococcus opacus showed the best growth of the tested species on plates with lignin. Further evaluation of P. fluorescens and R. opacus was made in liquid cultivations with depolymerized lignin (DL) at a concentration of 1 g/L. Size exclusion chromatography (SEC) showed that R. opacus consumed most of the available lower molecular weight compounds (approximately 0.1–0.4 kDa) in the DL, but the weight distribution of larger fractions was almost unaffected. Importantly, the consumed compounds included guaiacol—one of the main monomers in the DL. SEC analysis of P. fluorescens culture broth, in contrast, did not show a large conversion of low molecular weight compounds, and guaiacol remained unconsumed. However, a significant shift in molecular weight distribution towards lower average weights was seen.ConclusionsRhodococcus opacus and P. fluorescens were identified as two potential microbial candidates for the conversion/consumption of base-catalyzed depolymerized lignin, acting on low and high molecular weight lignin fragments, respectively. These findings will be of relevance for designing bioconversion of softwood Kraft lignin.Electronic supplementary materialThe online version of this article (10.1186/s13068-018-1240-7) contains supplementary material, which is available to authorized users.

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Section: Discussionsupporting

confidence: 77%

RETRACTED ARTICLE: Bacterial conversion of depolymerized Kraft lignin

Ravi

Abdelaziz

Nöbel

et al. 2018

Biotechnol Biofuels

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“…In this area, compounds with low RDB values and low numbers of carbon, hydrogen and oxygen atoms are projected. These compounds are likely to be lignin monomers, showing similar neutral losses compared to lignin oligomers [25]. Six of the compounds are projected close to the tetramer cluster, and therefore might be tetramers.…”

Section: Resultsmentioning

confidence: 99%

Identification of lignin oligomers in Kraft lignin using ultra-high-performance liquid chromatography/high-resolution multiple-stage tandem mass spectrometry (UHPLC/HRMSn)

et al. 2018

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Kraft lignin is the main source of technically produced lignin. For the development of valuable products based on Kraft lignin, its molecular structure is important. However, the chemical composition of Kraft lignin is still not well known. So far, the analysis of Kraft lignin by mass spectrometry (MS) has been mainly focused on monomeric compounds. Previous MS studies on lignin oligomers (LOs) considered only synthesised LO standards and/or lignins produced by processes other than the Kraft process. Furthermore, published MS methods suffer from using high resolution only in the MS1 stage in multiple-stage tandem MS methods. A high resolution in all MSn stages would provide more detailed information about LO fragmentation pathways. Since lignin samples are complex mixtures of a large number of similar phenolic compounds, the selection of tentative LOs in the MS data is challenging. In this study, we present a method for non-targeted analysis of LOs in Kraft lignin using ultra-high-performance liquid chromatography/high-resolution multiple-stage tandem mass spectrometry (UHPLC/HRMSn). A pre-selection strategy for LOs has been established based on a data-dependent neutral loss MS3 method in combination with a principal component analysis-quadratic discriminant analysis classification model (PCA-QDA). The method was optimised using a design of experiments (DOE) approach. The developed approach improved the pre-selection of tentative LOs in complex mixtures. From 587 detected peaks, 36 peaks were identified as LOs. Graphical abstractᅟ Electronic supplementary materialThe online version of this article (10.1007/s00216-018-1400-4) contains supplementary material, which is available to authorized users.

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“…The LS substrate and reaction products were analysed using SFC-MS to reveal monomeric compounds present. Prior to analysis, the sample preparation was performed as described in our previously published method for the analysis of lignin monomers [26]; 10 mL of LS sample and the reaction product were acidified to pH 1 using 6 M HCl, and precipitates removed by centrifugation. The supernatants were extracted with 10 mL ethyl acetate (2 × 3 mL + 1 × 4 mL), and the corresponding extracts combined and the ethyl acetate evaporated under a nitrogen stream.…”

Section: Sfc-ms Analysismentioning

confidence: 99%

Oxidative Depolymerisation of Lignosulphonate Lignin into Low-Molecular-Weight Products with Cu–Mn/δ-Al2O3

et al. 2019

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Lignin depolymerisation receives great attention due to the pressing need to find sustainable alternatives to fossil sources for production of fuels and chemicals. In this study, alumina-supported Cu-Mn and Ni-Mo catalysts were tested for oxidative depolymerisation of a technical lignin stream-sodium lignosulphonates-to produce valuable low-molecular-weight aromatics that may be considered for applications in the fuels and chemicals sector. The reactions were performed at elevated temperature and oxygen pressure, and the product mixtures were analysed by size exclusion chromatography, two-dimensional nuclear magnetic resonance spectroscopy and supercritical fluid chromatography mass spectrometry. The best performance was obtained with Cu-Mn/δ-Al 2 O 3 , which was thoroughly characterised before and after use by nitrogen physisorption, scanning electron microscopy, energy dispersive spectroscopy, powder X-ray diffraction, thermal gravimetric analysis, inductively coupled plasma optical emission spectrometry and X-ray photoelectron spectroscopy. Major products identified were vanillin, p-hydroxybenzaldehyde, vanillic acid and p-hydroxybenzoic acid as well as smaller aliphatic aldehydes, acids and lactones.

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Ultra-high-performance supercritical fluid chromatography with quadrupole-time-of-flight mass spectrometry (UHPSFC/QTOF-MS) for analysis of lignin-derived monomeric compounds in processed lignin samples

Cited by 45 publications

References 28 publications

RETRACTED ARTICLE: Bacterial conversion of depolymerized Kraft lignin

RETRACTED ARTICLE: Bacterial conversion of depolymerized Kraft lignin

Identification of lignin oligomers in Kraft lignin using ultra-high-performance liquid chromatography/high-resolution multiple-stage tandem mass spectrometry (UHPLC/HRMSn)

Oxidative Depolymerisation of Lignosulphonate Lignin into Low-Molecular-Weight Products with Cu–Mn/δ-Al2O3

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