Chinese Journal of Catalysis ›› 2024, Vol. 67: 102-111.DOI: 10.1016/S1872-2067(24)60146-4
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Guang-Hui Lu, Jian Yu, Ning Li(
)
Received:2024-07-03
Accepted:2024-09-18
Online:2024-11-30
Published:2024-11-30
Contact:
Ning Li
Supported by:Guang-Hui Lu, Jian Yu, Ning Li. A chemoenzymatic cascade for sustainable production of chiral N-arylated aspartic acids from furfural and waste[J]. Chinese Journal of Catalysis, 2024, 67: 102-111.
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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(24)60146-4
Scheme 1. Catalytic synthesis of MA.
Fig. 1. Photooxygenation of FCA into HFO under different catalytic modes: (A) the reaction scheme; (B) HFO yield. Reaction conditions: 20 mmol L-1 FCA, 5 mol% TCPP, 20 mL carbonate buffer (0.34 mol L-1 Na2CO3/0.06 mol L-1 NaHCO3, pH = 8.5), green light, 25 °C; (1) batch reaction with 600 r min-1; (2) continuous flow reaction with 34.9 mL min-1 reaction mixture; (3) continuous flow reaction with 34.9 mL min-1 reaction mixture in the presence of 60 mol% ACT; (4) continuous flow reaction with 34.9 mL min-1 reaction mixture and 13 mL min-1 O2 in the presence of 60 mol% ACT.
Fig. 2. (A) Effect of PNP concentrations on electrocatalytic furfural oxidation. (B) Cyclic voltammograms of ACT in electrooxidation of furfural paired with different reduction reactions. (C) Effect of ACT loadings on electrocatalytic furfural oxidation. (D) Effect of PNP concentrations on photoelectrocatalytic FCA oxidation. Reaction conditions unless otherwise stated: anode chamber: 100 mmol L-1 furfural, 60 mol% ACT, 16 mL carbonate buffer (0.34 mol L-1 Na2CO3/0.06 mol L-1 NaHCO3, pH 10), 0.8 V vs. Ag/AgCl, 13 mL min-1 O2, 600 r min-1, 25 °C, 3 h; cathode chamber: 10 mmol L-1 PNP, 10 equiv. NaBH4, 16 mL 1 mol L-1 aqueous KOH, Cu(OH)2@CF; (A)10-40 mmol L-1 PNP; (C) 10 mol%-60 mol% ACT; (B) anode chamber: 100 mmol L-1 furfural, 20 mmol L-1 ACT, 16 mL carbonate buffer (0.34 mol L-1 Na2CO3/0.06 mol L-1 NaHCO3, pH = 10), 100 mV s-1 scan rate, 25 °C; cathode chamber: 16 mL 2 mol L-1 aqueous NaOH, Pt wire (HER); 16 mL 1 mol L-1 aqueous KOH (40 mmol L-1 PNP, 0.4 mol L-1 NaBH4), Cu(OH)2@CF (PNPH). (D) anode chamber: 100 mmol L-1 FCA, 20 mol% ACT, 1 mol% TCPP, 20 mL carbonate buffer (0.34 mol L-1 Na2CO3/0.06 mol L-1 NaHCO3, pH 10), 0.8 V vs. Ag/AgCl, 11.5 mL min-1 reaction mixture, 13 mL min-1 O2, 600 r min-1, 25 °C, 1 h; cathode chamber: 10-40 mmol L-1 PNP, 10 equiv. NaBH4, 16 mL 1 mol L-1 aqueous KOH, Cu(OH)2@CF.
Fig. 3. Concurrent photoelectrocatalytic oxidation of furfural to MA with (A) and without (B) pH control. Reaction conditions: anode chamber: 100 mmol L-1 furfural, 20 mol% ACT, 1 mol% TCPP, 20 mL carbonate buffer (1 mol L-1 Na2CO3/1 mol L-1 NaHCO3, pH = 10), green light, 0.8 V vs. Ag/AgCl, 11.5 mL min-1 reaction mixture, 13 mL min-1 O2, 600 r min-1, 25 °C, tuning pH to around 10 by Na2CO3 powder every 1 h for (A); cathode chamber: 40 mmol L-1 PNP, 0.4 mol L-1 NaBH4, 16 mL 1 mol L-1 aqueous KOH, Cu(OH)2@CF.
Fig. 4. Photoelectrocatalytic oxidation of furfural into MA in different concentrations of carbonate buffer. (A) 1 mol L-1 Na2CO3/1 mol L-1 NaHCO3; (B) 0.5 mol L-1 Na2CO3/0.5 mol L-1 NaHCO3; (C) 0.25 mol L-1 Na2CO3/0.25 mol L-1 NaHCO3. Reaction conditions: anode chamber: 100 mmol L-1 furfural, 20 mol% ACT, 1 mol% TCPP, 20 mL carbonate buffer (pH = 10), green light, 0.8 V vs. Ag/AgCl, 11.5 mL min-1 reaction mixture, 13 mL min-1 O2, 600 r min-1, 25 °C, with pH control; cathode chamber: 40 mmol L-1 PNP, 16 mL 1 mol L-1 aqueous KOH, NiBx@NF.
Fig. 5. Photoelectrosynthesis of MA driven by sunlight: (A) the set-up diagram; (B) time course of photoelectrocatalytic oxidation of furfural. Reaction conditions: anode chamber: 100 mmol L-1 furfural, 20 mol% ACT, 1 mol% TCPP, 20 mL carbonate buffer (1 mol L-1 Na2CO3/1 mol L-1 NaHCO3, pH 10), sunlight, 0.8 V vs. Ag/AgCl, 11.5 mL min-1 reaction mixture, 13 mL min-1 O2, 600 r min-1, 25-35 °C; cathode chamber: 40 mmol L-1 PNP, 16 mL 1 mol L-1 aqueous KOH, NiBx@NF.
Fig. 6. High-titer MA and FA synthesis. Reaction conditions: anode chamber: 100 mmol L-1 furfural, 20 mol% ACT, 1 mol% TCPP, 20 mL carbonate buffer (0.5 mol L-1 Na2CO3/0.5 mol L-1 NaHCO3, pH = 10), green light, 0.8 V vs. Ag/AgCl, 11.5 mL min-1 reaction mixture, 13 mL min-1 O2, 600 r min-1, 25 °C; cathode chamber: 40 mmol L-1 PNP, 16 mL 1 mol L-1 aqueous KOH, NiBx@NF, adding 40 mmol L-1 PNP at the 2nd hour; upon TCPP removal and tuning pH to 8.5, 1 mg mL-1 purified MaiA was added to initiate the isomerization at 25 °C and 500 r min-1. Arrows indicate the supplementation of approximately 100 mmol L-1 furfural.
Fig. 7. Paired photoelectrosynthesis of MA and PAP (A), MA and OAP (B), scheme of enzymatic synthesis of N-arylated (S)-aspartic acids (C) and HPLC analysis (D). Reaction conditions: (A) and (B): anode chamber: 100 mmol L-1 furfural, 20 mol% ACT, 1 mol% TCPP, 20 mL carbonate buffer (1 mol L-1 Na2CO3/1 mol L-1 NaHCO3, pH 10), green light, 0.8 V vs. Ag/AgCl, 11.5 mL min-1 reaction mixture, 13 mL min-1 O2, 600 r min-1, 25 °C; cathode chamber: 40 mmol L-1 ONP/PNP, 16 mL 1 mol L-1 aqueous KOH, NiBx@NF, N2; (D) samples: (a) the reaction mixture of enzymatic condensation of commercially available PAP and FA; (b) the reaction mixture of enzymatic condensation of PAP and FA obtained via paired photoelectro(bio)synthesis; (c) the reaction mixture of enzymatic condensation of OAP and FA obtained via paired photoelectro(bio)synthesis; (d) the mixture of standard chemicals; enzymatic reaction conditions: 1 mg mL-1 EDDS lyase, 5 mmol L-1 OAP/PAP, 50 mmol L-1 FA, 2 mL pH = 8.5 buffer containing 5% DMSO, 25 °C, 150 r min-1, N2, 24 h.
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