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. Author manuscript; available in PMC: 2022 Apr 7.
Published in final edited form as: J Am Chem Soc. 2021 Mar 29;143(13):5011–5021. doi: 10.1021/jacs.0c13164

Figure 1. Relative rates of monolignol oxidation and coupling product formation catalyzed by TvLac.

Figure 1.

Each monomer is present as an equimolar mixture with 1. 1, 3 and 4 are naturally-occurring monolignols; all others are synthetic. For substrate oxidation, data points indicate the mean of peak integrations for the corresponding monomer species (m/z of [M-H2O+H]+) detected by LC-MS; EIC integrations are normalized to the peak integration at the initial reaction time points per species. For coupling product formation, data points indicate the mean of peak integrations for the corresponding regioisomeric products detected by LC-MS (m/z of [M-H2O+H]+, a common ion to all regioisomeric products a-c); EIC integrations are normalized to the maximum product EIC integration observed over the entire time course; relative ratios of products are unchanged from the raw data. CA-CA (2) denotes the natural dimer, CA-X the heterocoupling product, and X-X the non-CA dimer, where X denotes the non-CA analogue. Error bars show standard deviations of data from triplicate reactions. Consumption of coupling products (e.g. 2 past ~5 min) is likely due to nonselective TvLac activity resulting in oligomerization