Catalytic conversion of biomass-derived compounds to various amino acids: status and perspectives
Benjing Xu1, Jinhang Dai2(), Ziting Du2, Fukun Li1,2(), Huan Liu2,3, Xingxing Gu2, Xingmin Wang2, Ning Li2, Jun Zhao4()
1. Engineering Research Center for Waste Oil Recovery Technology and Equipment of Ministry of Education, Chongqing Technology and Business University, Chongqing 400067, China 2. College of Environment and Resources, Chongqing Technology and Business University, Chongqing 400067, China 3. Key Laboratory of Energy Resource Utilization from Agriculture Residue, Academy of Agricultural Planning and Engineering, Ministry of Agriculture and Rural Affairs, Beijing 100125, China 4. Department of Biology, Hong Kong Baptist University, Hong Kong, China
Amino acids are important nitrogen-containing chemicals that have a variety of applications. Currently, fermentation is the widely employed method to produce amino acids; however, the products are mostly limited to natural amino acids in the L-configuration. Catalytic synthesis is an alternative approach for the synthesis of amino acids with different types and configurations, where the use of renewable biomass-based feedstocks is highly attractive. To date, several lignocellulose and triacylglycerol-derived intermediates, typically α-keto acids and α-hydroxyl acids, have been transformed into amino acids via the amination reaction in the presence of additional nitrogen sources (i.e., NH3·H2O). Making full use of inherent nitrogen in biomass (i.e., chitin and protein) to produce amino acids avoids the use of extra nitrogen sources and meets the requirements of green chemistry, which is attracting increasing attention. In this review, we summarize different chemical-catalytic systems for the transformation of biomass to amino acids. An outlook on the challenges and opportunities for more effective production of amino acids from biomass by catalytic methods is provided.
. [J]. Frontiers of Chemical Science and Engineering, 2023, 17(7): 817-829.
Benjing Xu, Jinhang Dai, Ziting Du, Fukun Li, Huan Liu, Xingxing Gu, Xingmin Wang, Ning Li, Jun Zhao. Catalytic conversion of biomass-derived compounds to various amino acids: status and perspectives. Front. Chem. Sci. Eng., 2023, 17(7): 817-829.
H Uneyama, H Kobayashi, N Tonouchi. New Functions and Potential Applications of Amino Acids, in Amino Acid Fermentation. Berlin: Springer, 2017, 273–287
M Breuer, K Ditrich, T Habicher, B Hauer, M Kesseler, R Sturmer, T Zelinski. Industrial methods for the production of optically active intermediates. Angewandte Chemie International Edition, 2004, 43(7): 788–824 https://doi.org/10.1002/anie.200300599
4
M D’Este, M Alvarado-Morales, I Angelidaki. Amino acids production focusing on fermentation technologies—a review. Biotechnology Advances, 2018, 36(1): 14–25 https://doi.org/10.1016/j.biotechadv.2017.09.001
5
W Masamba. Petasis vs. Strecker amino acid synthesis: convergence, divergence and opportunities in organic synthesis. Molecules, 2021, 26(6): 1707 https://doi.org/10.3390/molecules26061707
X Chen, S Song, H Li, G Gözaydın, N Yan. Expanding the boundary of biorefinery: organonitrogen chemicals from biomass. Accounts of Chemical Research, 2021, 54(7): 1711–1722 https://doi.org/10.1021/acs.accounts.0c00842
9
Z Zhang, J Song, B Han. Catalytic transformation of lignocellulose into chemicals and fuel products in ionic liquids. Chemical Reviews, 2017, 117(10): 6834–6880 https://doi.org/10.1021/acs.chemrev.6b00457
10
Y Liu, Y Nie, X Lu, X Zhang, H He, F Pan, L Zhou, X Liu, X Ji, S Zhang. Cascade utilization of lignocellulosic biomass to high-value products. Green Chemistry, 2019, 21(13): 3499–3535 https://doi.org/10.1039/C9GC00473D
11
Y Jing, Y Guo, Q Xia, X Liu, Y Wang. Catalytic production of value-added chemicals and liquid fuels from lignocellulosic biomass. Chem, 2019, 5(10): 2520–2546 https://doi.org/10.1016/j.chempr.2019.05.022
12
X Liu, F P Bouxin, J Fan, V L Budarin, C Hu, J H Clark. Recent advances in the catalytic depolymerization of lignin towards phenolic chemicals: a review. ChemSusChem, 2020, 13(17): 4296–4317 https://doi.org/10.1002/cssc.202001213
13
X Liu, Q Zhang, R Wang, H Li. Sustainable conversion of biomass-derived carbohydrates into lactic acid using heterogeneous catalysts. Current Green Chemistry, 2020, 7(3): 282–289 https://doi.org/10.2174/2213346106666191127123730
14
W Deng, P Wang, B Wang, Y Wang, L Yan, Y Li, Q Zhang, Z Cao, Y Wang. Transformation of cellulose and related carbohydrates into lactic acid with bifunctional Al(III)-Sn(II) catalysts. Green Chemistry, 2018, 20(3): 735–744 https://doi.org/10.1039/C7GC02975F
15
J Zhang, X Liu, M Sun, X Ma, Y Han. Direct conversion of cellulose to glycolic acid with a phosphomolybdic acid catalyst in a water medium. ACS Catalysis, 2012, 2(8): 1698–1702 https://doi.org/10.1021/cs300342k
16
A Bayu, S Karnjanakom, A Yoshida, K Kusakabe, A Abudula, G Guan. Polyoxomolybdates catalysed cascade conversions of cellulose to glycolic acid with molecular oxygen via selective aldohexoses pathways (an epimerization and a [2 + 4] retro-aldol reaction). Catalysis Today, 2019, 332: 28–34 https://doi.org/10.1016/j.cattod.2018.05.034
17
J Li, R Yang, S Xu, C Zhou, Y Xiao, C Hu, D C W Tsang. Biomass-derived polyols valorization towards glycolic acid production with high atom-economy. Applied Catalysis B: Environmental, 2022, 317: 121785 https://doi.org/10.1016/j.apcatb.2022.121785
18
T J Schwartz, S M Goodman, C M Osmundsen, E Taarning, M D Mozuch, J Gaskell, D Cullen, P J Kersten, J A Dumesic. Integration of chemical and biological catalysis: production of furylglycolic acid from glucose via cortalcerone. ACS Catalysis, 2013, 3(12): 2689–2693 https://doi.org/10.1021/cs400593p
P Maki-Arvela, I L Simakova, T Salmi, D Y Murzin. Production of lactic acid/lactates from biomass and their catalytic transformations to commodities. Chemical Reviews, 2014, 114(3): 1909–1971 https://doi.org/10.1021/cr400203v
21
Y Cao, D Chen, Y Meng, S Saravanamurugan, H Li. Visible-light-driven prompt and quantitative production of lactic acid from biomass sugars over a N-TiO2 photothermal catalyst. Green Chemistry, 2021, 23(24): 10039–10049 https://doi.org/10.1039/D1GC03057D
22
Y Wang, S Furukawa, S Song, Q He, H Asakura, N Yan. Catalytic production of alanine from waste glycerol. Angewandte Chemie International Edition, 2020, 59(6): 2289–2293 https://doi.org/10.1002/anie.201912580
23
S Xu, Q Tian, Y Xiao, W Zhang, S Liao, J Li, C Hu. Regulating the competitive reaction pathway in glycerol conversion to lactic acid/glycolic acid selectively. Journal of Catalysis, 2022, 413: 407–416 https://doi.org/10.1016/j.jcat.2022.07.003
24
M Kitamura, D Lee, S Hayashi, S Tanaka, M Yoshimura. Catalytic Leuckart–Wallach-type reductive amination of ketones. Journal of Organic Chemistry, 2002, 67(24): 8685–8687 https://doi.org/10.1021/jo0203701
25
R Kadyrov, T H Riermeier, U Dingerdissen, V Tararov, A Borner. The first highly enantioselective homogeneously catalyzed asymmetric reductive amination: synthesis of α-N-benzylamino acids. Journal of Organic Chemistry, 2003, 68(10): 4067–4070 https://doi.org/10.1021/jo020690k
26
S Ogo, K Uehara, T Abura, S Fukuzumi. pH-Dependent chemoselective synthesis of α-amino acids. Reductive amination of α-keto acids with ammonia catalyzed by acid-stable iridium hydride complexes in water. Journal of the American Chemical Society, 2004, 126(10): 3020–3021 https://doi.org/10.1021/ja031633r
27
D P Nguyen, R N Sladek, L H Do. Scope and limitations of reductive amination catalyzed by half-sandwich iridium complexes under mild reaction conditions. Tetrahedron Letters, 2020, 61(32): 152196 https://doi.org/10.1016/j.tetlet.2020.152196
28
K Tanaka, T Miki, K Murata, A Yamaguchi, Y Kayaki, S Kuwata, T Ikariya, M Watanabe. Reductive amination of ketonic compounds catalyzed by cp*Ir(III) complexes bearing a picolinamidato ligand. Journal of Organic Chemistry, 2019, 84(17): 10962–10977 https://doi.org/10.1021/acs.joc.9b01565
29
K Harada, K Matsumot. Sterically controlled syntheses of optically active alpha-amino acids from alpha-keto acids by reductive amination. Journal of Organic Chemistry, 1967, 32(6): 1794 https://doi.org/10.1021/jo01281a020
30
K H ChangY K KwonG J Kim. The synthesis of optically active amino acid over Pd catalysts impregnated on mesoporous support. In: Studies in Surface Science and Catalysis. Amsterdam: Elsevier, 2003: 469–472
31
A S C Chan, C C Chen, Y C Lin. Catalytic reductive amination of alpha-ketocaboxylic acids as a useful route to amino-acids. Applied Catalysis A: General, 1994, 119(1): L1–L5 https://doi.org/10.1016/0926-860X(94)85018-6
32
L M Barge, E Flores, M M Baum, D G VanderVelde, M J Russell. Redox and pH gradients drive amino acid synthesis in iron oxyhydroxide mineral systems. Proceedings of the National Academy of Sciences of the United States of America, 2019, 116(11): 4828–4833 https://doi.org/10.1073/pnas.1812098116
33
C H Lam, W Deng, L Lang, X Jin, X Hu, Y Wang. Mini review on bio-oil upgrading via electrocatalytic hydrogenation: connecting biofuel production with renewable power. Energy & Fuels, 2020, 34(7): 7915–7928 https://doi.org/10.1021/acs.energyfuels.0c01380
34
T Fukushima, M Yamauchi. Electrosynthesis of amino acids from biomass-derivable acids on titanium dioxide. Chemical Communications, 2019, 55(98): 14721–14724 https://doi.org/10.1039/C9CC07208J
35
M Isegawa, A Staykov, M Yamauchi. Proton-coupled electron transfer in electrochemical alanine formation from pyruvic acid: mechanism of catalytic reaction at the interface between TiO2 (101) and water. Journal of Physical Chemistry C, 2021, 125(23): 12603–12613 https://doi.org/10.1021/acs.jpcc.1c01304
36
T Fukushima, M Yamauchi. Electrosynthesis of glycine from bio-derivable oxalic acid. Journal of Applied Electrochemistry, 2021, 51(1): 99–106 https://doi.org/10.1007/s10800-020-01428-x
37
Y Wan, J M Lee. Toward value-added dicarboxylic acids from biomass derivatives via thermocatalytic conversion. ACS Catalysis, 2021, 11(5): 2524–2560 https://doi.org/10.1021/acscatal.0c05419
38
W P Deng, Y Z Wang, S Zhang, K M Gupta, M J Hulsey, H Asakura, L M Liu, Y Han, E M Karp, G T Beckham, P J Dyson, J Jiang, T Tanaka, Y Wang, N Yan. Catalytic amino acid production from biomass-derived intermediates. Proceedings of the National Academy of Sciences of the United States of America, 2018, 115(20): 5093–5098 https://doi.org/10.1073/pnas.1800272115
39
Z Xie, B Chen, F Peng, M Liu, H Liu, G Yang, B Han. Highly efficient synthesis of amino acids by amination of bio-derived hydroxy acids with ammonia over Ru supported on N-doped carbon nanotubes. ChemSusChem, 2020, 13(21): 5683–5689 https://doi.org/10.1002/cssc.202001561
40
M A Shah, I Khalil, S Tallarico, T Donckels, P Eloy, D P Debecker, M Oliverio, M Dusselier. Catalytic amination of lactic acid using Ru-zeolites. Dalton Transactions, 2022, 51(28): 10773–10778 https://doi.org/10.1039/D2DT00054G
41
H Xin, Z Xiu, S Liu, H Wang, C Wang, L Ma, Q Liu. Efficient conversion of lactic acid to alanine over noble metal supported on Ni@C catalysts. RSC Advances, 2022, 12(26): 16847–16859 https://doi.org/10.1039/D2RA02514K
42
S Tian, Y Jiao, Z Gao, Y Xu, L Fu, H Fu, W Zhou, C Hu, G Liu, M Wang, D Ma. Catalytic amination of polylactic acid to alanine. Journal of the American Chemical Society, 2021, 143(40): 16358–16363 https://doi.org/10.1021/jacs.1c08159
43
S Song, J Qu, P Han, M J Hulsey, G Zhang, Y Wang, S Wang, D Chen, J Lu, N Yan. Visible-light-driven amino acids production from biomass-based feedstocks over ultrathin CdS nanosheets. Nature Communications, 2020, 11(1): 4899 https://doi.org/10.1038/s41467-020-18532-3
44
M Zheng, Q Li, M Liu, J Liu, C Zhao, X Xiao, H Wang, J Zhou, L Zhang, B Jiang. Creation of Mo active sites on indium oxide microrods for photocatalytic amino acid production. Science China Materials, 2022, 65(5): 1285–1293 https://doi.org/10.1007/s40843-021-1907-3
45
X Jin, K Meng, G Zhang, M Liu, Y Song, Z Song, C Yang. Interfacial catalysts for sustainable chemistry: advances on atom and energy efficient glycerol conversion to acrylic acid. Green Chemistry, 2021, 23(1): 51–76 https://doi.org/10.1039/D0GC02913K
46
T Li, D A Harrington. An overview of glycerol electrooxidation mechanisms on Pt, Pd and Au. ChemSusChem, 2021, 14(6): 1472–1495 https://doi.org/10.1002/cssc.202002669
47
Z Jiang, D Hu, Z Zhao, Z Yi, Z Chen, K Yan. Mini-review on the synthesis of furfural and levulinic acid from lignocellulosic biomass. Processes, 2021, 9(7): 1234 https://doi.org/10.3390/pr9071234
48
S Song, V F K Yuen, L Di, Q Sun, K Zhou, N Yan. Integrating biomass into the organonitrogen chemical supply chain: production of pyrrole and D-proline from furfural. Angewandte Chemie International Edition, 2020, 59(45): 19846–19850 https://doi.org/10.1002/anie.202006315
49
F De Schouwer, L Claes, A Vandekerkhove, J Verduyckt, D E De Vos. Protein-rich biomass waste as a resource for future biorefineries: state of the art, challenges, and opportunities. ChemSusChem, 2019, 12(7): 1272–1303 https://doi.org/10.1002/cssc.201802418
J Dai, F Li, X Fu. Towards shell biorefinery: advances in chemical-catalytic conversion of chitin biomass to organonitrogen chemicals. ChemSusChem, 2020, 13(24): 6498–6508 https://doi.org/10.1002/cssc.202001955
52
X Shi, X Ye, H Zhong, T Wang, F Jin. Sustainable nitrogen-containing chemicals and materials from natural marine resources chitin and microalgae. Molecular Catalysis, 2021, 505: 111517 https://doi.org/10.1016/j.mcat.2021.111517
53
J L Zhang, W S Xia, P Liu, Q Y Cheng, T Tahirou, W X Gu, B Li. Chitosan modification and pharmaceutical/biomedical applications. Marine Drugs, 2010, 8(7): 1962–1987 https://doi.org/10.3390/md8071962
54
H Pringsheim, G Ruschmann. Zur Darstellung der Glucosaminsäure. European Journal of Inorganic Chemistry, 1915, 48(1): 680–682
55
M Wolfrom, M Cron. Acyl derivatives of D-glucosaminic acid. Journal of the American Chemical Society, 1952, 74(7): 1715–1716 https://doi.org/10.1021/ja01127a030
56
W X Gu, W S Xia. Catalytic synthesis of D-glucosaminic acid from D-glucosamine on active charcoal-supported Pd-Bi catalysts. Journal of Carbohydrate Chemistry, 2006, 25(4): 297–301 https://doi.org/10.1080/07328300600723757
57
Y Ohmi, S Nishimura, K Ebitani. Synthesis of alpha-amino acids from glucosamine-HCl and its derivatives by aerobic oxidation in water catalyzed by Au nanoparticles on basic supports. ChemSusChem, 2013, 6(12): 2259–2262 https://doi.org/10.1002/cssc.201300303
58
Y ZhengD XuL ZhangX Chen. Base-free air oxidation of chitin-derived glucosamine to glucosaminic acid by zinc oxide-supported gold nanoparticles. Chemistry−An Asian Journal, 2022, 17(18)
59
J H Dai, G Gozaydin, C W Hu, N Yan. Catalytic conversion of chitosan to glucosaminic acid by tandem hydrolysis and oxidation. ACS Sustainable Chemistry & Engineering, 2019, 7(14): 12399–12407 https://doi.org/10.1021/acssuschemeng.9b01912
60
P Hu, Y Ben-David, D Milstein. General synthesis of amino acid salts from amino alcohols and basic water liberating H2. Journal of the American Chemical Society, 2016, 138(19): 6143–6146 https://doi.org/10.1021/jacs.6b03488
61
K Techikawara, H Kobayashi, A Fukuoka. Conversion of N-acetylglucosamine to protected amino acid over Ru/C catalyst. ACS Sustainable Chemistry & Engineering, 2018, 6(9): 12411–12418 https://doi.org/10.1021/acssuschemeng.8b02951
62
C Della Pina, E Falletta, L Prati, M Rossi. Selective oxidation using gold. Chemical Society Reviews, 2008, 37(9): 2077–2095 https://doi.org/10.1039/b707319b
63
S Biella, G Castiglioni, C Fumagalli, L Prati, M Rossi. Application of gold catalysts to selective liquid phase oxidation. Catalysis Today, 2002, 72(1-2): 43–49 https://doi.org/10.1016/S0920-5861(01)00476-X
64
A Villa, S Campisi, M Schiavoni, L Prati. Amino alcohol oxidation with gold catalysts: the effect of amino groups. Materials, 2013, 6(7): 2777–2788 https://doi.org/10.3390/ma6072777
65
X Meng, Y Bai, H Xu, Y Zhang, C Li, H Wang, Z Li. Selective oxidation of monoethanolamine to glycine over supported gold catalysts: the influence of support and the promoting effect of polyvinyl alcohol. Molecular Catalysis, 2019, 469: 131–143 https://doi.org/10.1016/j.mcat.2019.03.011
66
X Meng, Z Li, Y Zhang, R Yan, H Wang. Deactivation behavior and aggregation mechanism of supported Au nanoparticles in the oxidation of monoethanolamine to glycine. Catalysis Communications, 2020, 146: 106127 https://doi.org/10.1016/j.catcom.2020.106127
