|
|
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 |
|
|
Abstract 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.
|
Keywords
biomass
amino acids
chitin
nitrogen-containing compounds
lignocellulose
|
Corresponding Author(s):
Jinhang Dai,Fukun Li,Jun Zhao
|
About author: * These authors contributed equally to this work. |
Just Accepted Date: 26 October 2022
Online First Date: 28 February 2023
Issue Date: 05 July 2023
|
|
1 |
H Uneyama, H Kobayashi, N Tonouchi. New Functions and Potential Applications of Amino Acids, in Amino Acid Fermentation. Berlin: Springer, 2017, 273–287
|
2 |
V F Wendisch. Metabolic engineering advances and prospects for amino acid production. Metabolic Engineering, 2020, 58: 17–34
https://doi.org/10.1016/j.ymben.2019.03.008
|
3 |
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
|
6 |
N Yan, Y Wang. Catalyst: Is the amino acid a new frontier for biorefineries?. Chem, 2019, 5(4): 739–741
https://doi.org/10.1016/j.chempr.2019.03.016
|
7 |
J Ge, Q Song, Y Jia, W Yang. Reaction: a new option for producing amino acids from renewable biomass?. Chem, 2019, 5(4): 742–743
https://doi.org/10.1016/j.chempr.2019.03.017
|
8 |
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
|
19 |
E Sjostrom. Carbohydrate degradation products from alkaline treatment of biomass. Biomass and Bioenergy, 1991, 1(1): 61–64
https://doi.org/10.1016/0961-9534(91)90053-F
|
20 |
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
|
50 |
M J Hulsey. Shell biorefinery: a comprehensive introduction. Green Energy & Environment, 2018, 3(4): 318–327
https://doi.org/10.1016/j.gee.2018.07.007
|
51 |
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
|
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
|
Shared |
|
|
|
|
|
Discussed |
|
|
|
|