3 methylcatechol

ADP, ascorbate, CCCP, duroquinol, ethylene glycol-bis (β-aminoethyl ether) N,N,Nʹ,Nʹ tetraacetic acid (EGTA), glutamate, 4-(2-hydroxy-ethyl)-l -piperazine-ethanesulfonic acid (HEPES), malate, succinate, N,N,Nʹ,Nʹ-tetramethyl-p-phenylenediamine (TMPD) and 3-methyl catechol were purchased from Sigma Chemical Co. (St. Louis, MO). Pentadecyl phenol was obtained from Cardolite Corporation (Bristol, PA USA). Duroquinol (Dur) was prepared from duroquinone as described previously [58 (link)]. Urushiols were dissolved in dimethyl sulfoxide (DMSO; Merck, Darmstadt, Germany). The solvent had no effect on respiration at any of the concentrations employed. All the other reagents were of the highest purity available.

The monomer 5,5′,6,6′-tetrahydroxy-3,3,3′,3′-tetramethyl-1,1′-spirobisindane (TTSBI, 97%) was obtained from ABCR (Karlsruhe, Germany) and 2,3,5,6-tetrafluoroterephtalonitrile (TFTDN) was kindly donated by Lanxess (Köln, Germany). TFTDN was sublimated twice at 80 °C and < 1 mbar prior to use. Potassium carbonate (K₂CO₃, >99,5%) was dried overnight at 120 °C under vacuum and then milled in a ball mill for 15 min.
For the synthesis of dimethyl-TTSBI (DMTTSBI) 3-methylcatechol, hydro bromic acid (HBr, 47% in H₂O) and acetic acid (HAc) were obtained from Sigma Aldrich. As well as benzoylperoxide (BPO, 75%), diethylbenzene (DEB), chlorobenzene (anhydrous) and sodium azide (99%) for further reactions. They were used as received. N-bromosuccinimide (NBS, ≥99%), N,N-dimethylacetamide (DMAc, ≥99.8%), N,N-dimethylformamide (DMF, ≥ 99.8%), chloroform (CHCl₃, 99.9%), methanol (CH₃OH, ≥99%) and acetone (≥99%) were obtained from Merck and used as received.

Regenerated amorphous cellulose (RAC) was prepared from Avicel PH-101 as previously described (Zhang and Lynd 2004 (link); Frommhagen et al. 2015 (link)). d-Glucose, d-gluconic acid, ascorbic acid, and 3-methylcatechol were purchased from Sigma-Aldrich (Steinheim, Germany). d-Cellobionic acid ammonium salt was obtained from Toronto Research Chemicals (Toronto, Ontario, Canada). Almond β-glucosidase was purchased from Sigma-Aldrich and had, according to the supplier’s information, a specific activity of 6 U mg⁻¹ lyophilized powder. Commercial cellulase mixtures Celluclast 1.5 L and Novozym 188 were obtained from Novozymes A/S (Bagsværd, Denmark).