Degradation pathways of amino acids during thermal utilization of biomass: a review

Abstract

Amino acids are important nitrogen carriers in biomass and entail a broad spectrum of industrial uses, most notably as food additives, pharmaceutical ingredients, and raw materials for bio-based plastics. Attaining detailed information in regard to the fragmentation of amino acids is essential to comprehend the nitrogen transformation chemistry at conditions encountered during hydrothermal and pyrolytic degradation of biomass. The underlying aim of this review is to survey literature studies pertinent to the complex structures of amino acids, their formation yields from various categories of biomass, and their fragmentation routes at elevated temperatures and in the aqueous media. Two predominant degradation reactions ensue in the decomposition of amino acids, namely deamination and decarboxylation. Notably, minor differences in structure can greatly affect the fate for each amino acid. Moreover, amino acids, being nitrogen-rich compounds, play pivotal roles across various fields. There is a growing interest in producing varied types and configurations of amino acids. Microbial fermentation appears to a viable approach to produce amino acids at an industrial scale. One innovative method under investigation is catalytic synthesis using renewable biomass as feedstocks. Such a method taps into the inherent nitrogen in biomass sources like chitin and proteins, eliminating the need for external nitrogen sources. This environmentally friendly approach is in line with green chemistry principles and has been gathering momentum in the scientific community.

Graphical abstract

Keywords

amino acids / pyrolysis / biomass / nitrogen / mechanisms / bioenergy

References

[1] Wang P , Shu C , Ye H , Biczysko M . Structural and energetic properties of amino acids and peptides benchmarked by accurate theoretical and experimental data. Journal of Physical Chemistry A, 2021, 125(45): 9826–9837

[2] Lee C Y , Chen J T , Chang W T , Shiah I M . Effect of pH on the solubilities of divalent and trivalent amino acids in water at 298.15 K. Fluid Phase Equilibria, 2013, 343(1): 30–35

[3] Pradhan A A , Vera J H . Effect of acids and bases on the solubility of amino acids. Fluid Phase Equilibria, 1998, 152(1): 121–132

[4] Lara-Popoca J , Thoke H S , Stock R P , Rudino-Pinera E , Bagatolli L A . Inductive effects in amino acids and peptides: ionization constants and tryptophan fluorescence. Biochemistry and Biophysics Reports, 2020, 24(1): 100802

[5] Bowden N A , Sanders J P M , Bruins M E . Solubility of the proteinogenic α-amino acids in water, ethanol, and ethanol-ater mixtures. Journal of Chemical & Engineering Data, 2018, 63(3): 488–497

[6] Petrotchenko E V , Borchers C H . Protein chemistry combined with mass spectrometry for protein structure determination. Chemical Reviews, 2022, 122(8): 7488–7499

[7] Nakashima H , Nishikawa K . Discrimination of intracellular and extracellular proteins using amino acid composition and residue-pair frequencies. Journal of Molecular Biology, 1994, 238(1): 54–61

[8] Rosenkranz A A , Slastnikova T A . Prospects of using protein engineering for selective drug delivery into a specific compartment of target cells. Pharmaceutics, 2023, 15(3): 987

[9] Stollar E J , Smith D P . Uncovering protein structure. Essays in Biochemistry, 2020, 64(4): 649–680

[10] Kirschning A . On the evolutionary history of the twenty encoded amino acids. Chemistry, 2022, 28(55): e202201419

[11] Xu Q , Deng H , Li X , Quan Z S . Application of amino acids in the structural modification of natural products: a review. Frontiers in Chemistry, 2021, 9(1): 1–26

[12] Huang Y , Ji X , Ma Z , Łężyk M , Xue Y , Zhao H . Green chemical and biological synthesis of cadaverine: recent development and challenges. RSC Advances, 2021, 11(39): 23922–23942

[13] Liu K , Shao B , Zheng B , Zong B . Catalytic production of functional monomers from lysine and their application in high-valued polymers. Catalysts, 2022, 13(1): 56

[14] Haeger G , Jolmes T , Oyen S , Jaeger K E , Bongaerts J , Schörken U , Siegert P . Novel recombinant aminoacylase from Paraburkholderia monticola capable of N-acyl-amino acid synthesis. Applied Microbiology and Biotechnology, 2024, 108(1): 93

[15] Heieck K , Arnold N D , Brück T B . Metabolic stress constrains microbial L-cysteine production in Escherichia coli by accelerating transposition through mobile genetic elements. Microbial Cell Factories, 2023, 22(1): 10

[16] D’Este M , Alvarado-Morales M , Angelidaki I . Amino acids production focusing on fermentation technologies: a review. Biotechnology Advances, 2018, 36(1): 14–25

[17] Cheng H , Zhu X , Zhu C , Qian J , Zhu N , Zhao L , Chen J . Hydrolysis technology of biomass waste to produce amino acids in sub-critical water. Bioresource Technology, 2008, 99(9): 3337–3341

[18] Goto M , Obuchi R , Hirose T , Sakaki T , Shibata M . Hydrothermal conversion of municipal organic waste into resources. Bioresource Technology, 2004, 93(3): 279–284

[19] Klejdus B , Lojková L , Kula E , Buchta I , Hrdlička P , Kubáň V . Supercritical fluid extraction of amino acids from birch (Betula pendula Roth) leaves and their liquid chromatographic determination with fluorimetric detection. Journal of Separation Science, 2008, 31(8): 1363–1373

[20] Pourali O , Asghari F S , Yoshida H . Sub-critical water treatment of rice bran to produce valuable materials. Food Chemistry, 2009, 115(1): 1–7

[21] Sereewatthanawut I , Prapintip S , Watchiraruji K , Goto M , Sasaki M , Shotipruk A . Extraction of protein and amino acids from deoiled rice bran by subcritical water hydrolysis. Bioresource Technology, 2008, 99(3): 555–561

[22] Duchiron S W , Pollet E , Givry S , Avérous L . Enzymatic synthesis of amino acids endcapped polycaprolactone: a green route towards functional polyesters. Molecules, 2018, 23(2): 290

[23] Grasso F , Méndez-Paz D , Vázquez Sobrado R , Orlandi V , Turrini F , De Negri Atanasio G , Grasselli E , Tiso M , Boggia R . Feasibility of enzymatic protein extraction from a dehydrated fish biomass obtained from unsorted canned yellowfin tuna side streams: Part I. Gels, 2023, 9(9): 760

[24] Wagner A J , Zubarev D Y , Aspuru-Guzik A , Blackmond D G . Chiral sugars drive enantioenrichment in prebiotic amino acid synthesis. ACS Central Science, 2017, 3(4): 322–328

[25] Schaberg A , Wroblowski R , Goertz R . Comparative study of the thermal decomposition behaviour of different amino acids and peptides. Journal of Physics: Conference Series, 2018, 1107(3): 032013

[26] Körner P . Hydrothermal degradation of amino acids. ChemSusChem, 2021, 14(22): 4947–4957

[27] Jeong Y , Kim H W , Ku J , Seo J . Breakdown of chiral recognition of amino acids in reduced dimensions. Scientific Reports, 2020, 10(1): 16166

[28] Inaki M , Liu J , Matsuno K . Cell chirality: its origin and roles in left-right asymmetric development. Philosophical Transactions of the Royal Society B: Biological Sciences, 2016, 371(1710): 20150403

[29] Cava F , Lam H , de Pedro M A , Waldor M K . Emerging knowledge of regulatory roles of D-amino acids in bacteria. Cellular and Molecular Life Sciences, 2011, 68(5): 817–831

[30] Kühnle A , Linderoth T R , Hammer B , Besenbacher F . Chiral recognition in dimerization of adsorbed cysteine observed by scanning tunnelling microscopy. Nature, 2002, 415(6874): 891–893

[31] Chen Q , Richardson N V . Enantiomeric interactions between nucleic acid bases and amino acids on solid surfaces. Nature Materials, 2003, 2(5): 324–328

[32] Lopinski G P , Moffatt D J , Wayner D D M , Wolkow R A . Determination of the absolute chirality of individual adsorbed molecules using the scanning tunnelling microscope. Nature, 1998, 392(6679): 909–911

[33] Zhang J , Li B , Cui X , Wang B , Yang J , Hou J G . Spontaneous chiral resolution in supramolecular assembly of 2,4,6-tris(2-pyridyl)-1,3,5-triazine on Au(111). Journal of the American Chemical Society, 2009, 131(16): 5885–5890

[34] Harms M J , Castañeda C A , Schlessman J L , Sue G R , Isom D G , Cannon B R , García-Moreno E B . The pK(a) values of acidic and basic residues buried at the same internal location in a protein are governed by different factors. Journal of Molecular Biology, 2009, 389(1): 34–47

[35] MehtaK KVedanthamG. Next-Generation Process Design for Monoclonal Antibody Purification, in Biopharmaceutical Processing. Jagschies G, Lindskog E, Łącki K, Galliher P, eds. Amsterdam: Elsevier, 2018, 793–811

[36] Pace C N , Grimsley G R , Scholtz J M . Protein ionizable groups: pK values and their contribution to protein stability and solubility. Journal of Biological Chemistry, 2009, 284(20): 13285–13289

[37] Chipens G I , Balodis I , Gnilomedova L E . Polarity and hydropathic properties of natural amino acids. Ukrainskii Biokhimicheskii Zhurnal, 1991, 63(4): 20–29

[38] KalidasCSangaranarayananM V. Amino Acids in Biophysical Chemistry: Techniques and Applications. Kalidas C, Sangaranarayanan M V, eds. Cham: Springer Nature Switzerland, 2023, 115–127

[39] SelvarajCDineshD CRajaramKSundaresanSSinghS K. Macromolecular chemistry: an introduction. In: In Silico Approaches to Macromolecular Chemistry, Thomas M E, Thomas J, Thomas S, Kornweitz H, eds. Amsterdam: Elsevier, 2023, 71–128

[40] Bellissent-Funel M C , Hassanali A , Havenith M , Henchman R , Pohl P , Sterpone F , van der Spoel D , Xu Y , Garcia A E . Water determines the structure and dynamics of proteins. Chemical Reviews, 2016, 116(13): 7673–7697

[41] Melnikov S , Mailliot J , Rigger L , Neuner S , Shin B S , Yusupova G , Dever T E , Micura R , Yusupov M . Molecular insights into protein synthesis with proline residues. EMBO Reports, 2016, 17(12): 1776–1784

[42] Stipanuk M H . Metabolism of sulfur-containing amino acids: how the body copes with excess methionine, cysteine, and sulfide. Journal of Nutrition, 2020, 150(1): 2494S–2505S

[43] Poole L B . The basics of thiols and cysteines in redox biology and chemistry. Free Radical Biology & Medicine, 2015, 80(1): 148–157

[44] KohlmeierM. Nutrient Metabolism. 1st ed. London: Academic Press, 2003, 389–395

[45] El-FawalH A N. Neurotoxicology. In: Encyclopedia of Environmental Health (2nd Edition). Nriagu J ed. Oxford: Elsevier, 2011, 614–633

[46] André I , Linse S , Mulder F A A . Residue-specific pK_a determination of lysine and arginine side chains by indirect ¹⁵N and ¹³C NMR spectroscopy: application to apo calmodulin. Journal of the American Chemical Society, 2007, 129(51): 15805–15813

[47] Zhu C , Gao Y , Li H , Meng S , Li L , Francisco J S , Zeng X C . Characterizing hydrophobicity of amino acid side chains in a protein environment via measuring contact angle of a water nanodroplet on planar peptide network. Proceedings of the National Academy of Sciences of the United States of America, 2016, 113(46): 12946–12951

[48] BhagavanN VHaC E. Three-dimensional structure of proteins and disorders of protein misfolding. In: Essentials of Medical Biochemistry (2nd Edition), Bhagavan N V, Ha C E, Eds. San Diego: Academic Press, 2015, 31–51

[49] PelleyJ W. Protein Structure and Function, in Elsevier’s Integrated Biochemistry. Pelley J W, eds. Philadelphia: Mosby, 2007, 19–28

[50] Ogo S , Uehara K , Abura T , Fukuzumi S . 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

[51] Zuend S J , Coughlin M P , Lalonde M P , Jacobsen E N . Scaleable catalytic asymmetric Strecker syntheses of unnatural α-amino acids. Nature, 2009, 461(7266): 968–970

[52] Zhang M , Imm S , Bähn S , Neumann H , Beller M . Synthesis of α-amino acid amides: ruthenium-catalyzed amination of α-hydroxy amides. Angewandte Chemie International Edition, 2011, 50(47): 11197–11201

[53] Magrino T , Pietrucci F , Saitta A M . Step by step strecker amino acid synthesis from ab initio prebiotic chemistry. Journal of Physical Chemistry Letters, 2021, 12(10): 2630–2637

[54] Hu P , Ben-David Y , Milstein D . 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

[55] Deng W , Wang Y , Zhang S , Gupta K M , Hülsey M J , Asakura H , Liu L , Han Y , Karp E M , Beckham G T . . 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

[56] Xu B , Dai J , Du Z , Li F , Liu H , Gu X , Wang X , Li N , Zhao J . Catalytic conversion of biomass-derived compounds to various amino acids: status and perspectives. Frontiers of Chemical Science and Engineering, 2023, 17(7): 817–829

[57] Liu X , Zhang Q , Wang R , Li H . Sustainable conversion of biomass-derived carbohydrates into lactic acid using heterogeneous catalysts. Current Green Chemistry, 2020, 7(3): 282–289

[58] Deng W , Wang P , Wang B , Wang Y , Yan L , Li Y , Zhang Q , Cao Z , Wang Y . Transformation of cellulose and related carbohydrates into lactic acid with bifunctional Al(III)-Sn(II) catalysts. Green Chemistry, 2018, 20(3): 735–744

[59] Li J , Yang R , Xu S , Zhou C , Xiao Y , Hu C , Tsang D C W . Biomass-derived polyols valorization towards glycolic acid production with high atom-economy. Applied Catalysis B: Environmental, 2022, 317(1): 121785

[60] Sjöström E . Carbohydrate degradation products from alkaline treatment of biomass. Biomass and Bioenergy, 1991, 1(1): 61–64

[61] Cao Y , Chen D , Meng Y , Saravanamurugan S , Li H . 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

[62] Wang Y , Furukawa S , Song S , He Q , Asakura H , Yan N . Catalytic production of alanine from waste glycerol. Angewandte Chemie International Edition, 2020, 59(6): 2289–2293

[63] Xu S , Tian Q , Xiao Y , Zhang W , Liao S , Li J , Hu C . Regulating the competitive reaction pathway in glycerol conversion to lactic acid/glycolic acid selectively. Journal of Catalysis, 2022, 413(1): 407–416

[64] Besson M , Gallezot P , Pinel C . Conversion of biomass into chemicals over metal catalysts. Chemical Reviews, 2014, 114(3): 1827–1870

[65] Li C , Zhao X , Wang A , Huber G W , Zhang T . Catalytic transformation of lignin for the production of chemicals and fuels. Chemical Reviews, 2015, 115(21): 11559–11624

[66] Key R E , Bozell J J . Progress toward lignin valorization via selective catalytic technologies and the tailoring of biosynthetic pathways. ACS Sustainable Chemistry & Engineering, 2016, 4(10): 5123–5135

[67] Xing R , Qi W , Huber G W . Production of furfural and carboxylic acids from waste aqueous hemicellulose solutions from the pulp and paper and cellulosic ethanol industries. Energy & Environmental Science, 2011, 4(6): 2193–2205

[68] de Clippel F , Dusselier M , Van Rompaey R , Vanelderen P , Dijkmans J , Makshina E , Giebeler L , Oswald S , Baron G V , Denayer J F M . . Fast and selective sugar conversion to alkyl lactate and lactic acid with bifunctional carbon-silica catalysts. Journal of the American Chemical Society, 2012, 134(24): 10089–10101

[69] Weingarten R , Kim Y T , Tompsett G A , Fernández A , Han K S , Hagaman E W , Conner W C Jr , Dumesic J A , Huber G W . Conversion of glucose into levulinic acid with solid metal(IV) phosphate catalysts. Journal of Catalysis, 2013, 304: 123–134

[70] Anderson E , Katahira R , Reed M , Resch M , Karp E , Beckham G , Roman-Leshkov Y . Reductive catalytic fractionation of corn stover lignin. ACS Sustainable Chemistry & Engineering, 2016, 4(12): 6940–6950

[71] Choi Y S , Singh R , Zhang J , Balasubramanian G , Sturgeon M R , Katahira R , Chupka G , Beckham G T , Shanks B H . Pyrolysis reaction networks for lignin model compounds: unraveling thermal deconstruction of β-O-4 and α-O-4 compounds. Green Chemistry, 2016, 18(6): 1762–1773

[72] Tang Z , Deng W , Wang Y , Zhu E , Wan X , Zhang Q , Wang Y . Transformation of cellulose and its derived carbohydrates into formic and lactic acids catalyzed by vanadyl cations. ChemSusChem, 2014, 7(6): 1557–1567

[73] Wang F F , Liu C L , Dong W S . Highly efficient production of lactic acid from cellulose using lanthanide triflate catalysts. Green Chemistry, 2013, 15(8): 2091–2095

[74] Li L , Shen F , Smith R L , Qi X . Quantitative chemocatalytic production of lactic acid from glucose under anaerobic conditions at room temperature. Green Chemistry, 2017, 19(1): 76–81

[75] Kawaguchi H , Uematsu K , Ogino C , Teramura H , Nakamura S , Tsuge Y , Hasunuma T , Oinuma K I , Takaya N , Kondo A . Simultaneous saccharification and fermentation of kraft pulp by recombinant Escherichia coli for phenyllactic acid production. Biochemical Engineering Journal, 2014, 88(1): 188–194

[76] Ralph J . Hydroxycinnamates in lignification. Phytochemistry Reviews, 2010, 9(1): 65–83

[77] Gunanathan C , Milstein D . Selective synthesis of primary amines directly from alcohols and ammonia. Angewandte Chemie International Edition, 2008, 47(45): 8661–8664

[78] Pingen D , Müller C , Vogt D . Direct amination of secondary alcohols using ammonia. Angewandte Chemie International Edition, 2010, 49(44): 8130–8133

[79] Tomer A , Wyrwalski F , Przybylski C , Paul J F , Monflier E , Pera-Titus M , Ponchel A . Facile preparation of Ni/Al₂O₃ catalytic formulations with the aid of cyclodextrin complexes: towards highly active and robust catalysts for the direct amination of alcohols. Journal of Catalysis, 2017, 356: 111–124

[80] Alshammari A , Murugesan K . MOF-derived cobalt nanoparticles catalyze a general synthesis of amines. Science, 2017, 358(6361): 326–332

[81] Watson A J , Williams J M . The give and take of alcohol activation. Science, 2010, 329(5992): 635–636

[82] Tonouchi N , Ito H . Present global situation of amino acids in industry. Advances in Biochemical Engineering/Biotechnology, 2017, 159(1): 3–14

[83] Xie Z , Chen B , Peng F , Liu M , Liu H , Yang G , Han B . 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

[84] Kitamura M , Lee D , Hayashi S , Tanaka S , Yoshimura M . Catalytic Leuckart-Wallach-type reductive amination of ketones. Journal of Organic Chemistry, 2002, 67(24): 8685–8687

[85] Kadyrov R , Riermeier T H , Dingerdissen U , Tararov V , Börner A . The first highly enantioselective homogeneously catalyzed asymmetric reductive amination: synthesis of alpha-N-benzylamino acids. Journal of Organic Chemistry, 2003, 68(10): 4067–4070

[86] Nguyen D P , Sladek R N , Do L H . Scope and limitations of reductive amination catalyzed by half-sandwich iridium complexes under mild reaction conditions. Tetrahedron Letters, 2020, 61(32): 152–196

[87] Chan A S C , Chen C C , Lin Y C . Catalytic reductive amination of α-ketocaboxylic acids as a useful route to amino acids. Applied Catalysis A, General, 1994, 119(1): L1–L5

[88] Dai J , Li F , Fu X . Towards shell biorefinery: advances in chemical-catalytic conversion of chitin biomass to organonitrogen chemicals. ChemSusChem, 2020, 13(24): 6498–6508

[89] Yan N , Chen X . Sustainability: don’t waste seafood waste. Nature, 2015, 524(7564): 155–157

[90] ChenXYangHYanN. Shell biorefinery: dream or reality? Chemistry, 2016, 22(38): 13402–13421

[91] Yang H , Gözaydın G , Nasaruddin R R , Har J R G , Chen X , Wang X , Yan N . Toward the shell biorefinery: processing crustacean shell waste using hot water and carbonic acid. ACS Sustainable Chemistry & Engineering, 2019, 7(5): 5532–5542

[92] Duan B , Zheng X , Xia Z , Fan X , Guo L , Liu J , Wang Y , Ye Q , Zhang L . Highly biocompatible nanofibrous microspheres self-assembled from chitin in NaOH/urea aqueous solution as cell carriers. Angewandte Chemie International Edition, 2015, 54(17): 5152–5156

[93] Dai J , Gözaydın G , Hu C , Yan N . Catalytic conversion of chitosan to glucosaminic acid by tandem hydrolysis and oxidation. ACS Sustainable Chemistry & Engineering, 2019, 7(14): 12399–12407

[94] Kruse A , Dahmen N . Water—a magic solvent for biomass conversion. Journal of Supercritical Fluids, 2015, 96(1): 36–45

[95] Libra J A , Ro K S , Kammann C , Funke A , Berge N D , Neubauer Y , Titirici M M , Fühner C , Bens O , Kern J . . Hydrothermal carbonization of biomass residuals: a comparative review of the chemistry, processes and applications of wet and dry pyrolysis. Biofuels, 2011, 2(1): 71–106

[96] Kruse A , Funke A , Titirici M M . Hydrothermal conversion of biomass to fuels and energetic materials. Current Opinion in Chemical Biology, 2013, 17(3): 515–521

[97] Zhang B , Biswal B K , Zhang J , Balasubramanian R . Hydrothermal treatment of biomass feedstocks for sustainable production of chemicals, fuels, and materials: progress and perspectives. Chemical Reviews, 2023, 123(11): 7193–7294

[98] Gwyther C L , Williams A P , Golyshin P N , Edwards-Jones G , Jones D L . The environmental and biosecurity characteristics of livestock carcass disposal methods: a review. Waste Management, 2011, 31(4): 767–778

[99] Pietrucci F , Aponte J C , Starr R , Pérez-Villa A , Elsila J E , Dworkin J P , Saitta A M . Hydrothermal decomposition of amino acids and origins of prebiotic meteoritic organic compounds. ACS Earth & Space Chemistry, 2018, 2(6): 588–598

[100] Changi S , Zhu M , Savage P E . Hydrothermal reaction kinetics and pathways of phenylalanine alone and in binary mixtures. ChemSusChem, 2012, 5(9): 1743–1757

[101] Sato N , Quitain A T , Kang K , Daimon H , Fujie K . Reaction kinetics of amino acid decomposition in high-temperature and high-pressure water. Industrial & Engineering Chemistry Research, 2004, 43(13): 3217–3222

[102] Faisal M , Sato N , Quitain A T , Daimon H , Fujie K . Reaction kinetics and pathway of hydrothermal decomposition of aspartic acid. International Journal of Chemical Kinetics, 2007, 39(3): 175–180

[103] Estrada C F , Mamajanov I , Hao J , Sverjensky D A , Cody G D , Hazen R M . Aspartate transformation at 200 °C with brucite [Mg(OH)₂], NH₃, and H₂: implications for prebiotic molecules in hydrothermal systems. Chemical Geology, 2017, 457(1): 162–172

[104] Vallentyne J R . Biogeochemistry of organic matter—II. Thermal reaction kinetics and transformation products of amino compounds. Geochimica et Cosmochimica Acta, 1964, 28(2): 157–188

[105] Qian Y , Engel M H , Macko S A , Carpenter S , Deming J W . Kinetics of peptide hydrolysis and amino acid decomposition at high temperature. Geochimica et Cosmochimica Acta, 1993, 57(14): 3281–3293

[106] Andersson E , Holm N G . The stability of some selected amino acids under attempted redox constrained hydrothermal conditions. Origins of Life and Evolution of the Biosphere, 2000, 30(1): 9–23

[107] Bada J L , Miller S L , Zhao M . The stability of amino acids at submarine hydrothermal vent temperatures. Origins of Life and Evolution of the Biosphere, 1995, 25(1): 111–118

[108] Rogalinski T , Herrmann S , Brunner G . Production of amino acids from bovine serum albumin by continuous sub-critical water hydrolysis. Journal of Supercritical Fluids, 2005, 36(1): 49–58

[109] Zhu G , Zhu X , Fan Q , Wan X . Kinetics of amino acid production from bean dregs by hydrolysis in sub-critical water. Amino Acids, 2011, 40(4): 1107–1113

[110] Abdelmoez W , Nakahasi T , Yoshida H . Amino acid transformation and decomposition in saturated subcritical water conditions. Industrial & Engineering Chemistry Research, 2007, 46(16): 5286–5294

[111] Li J , Brill T B . Spectroscopy of hydrothermal reactions 25: kinetics of the decarboxylation of protein amino acids and the effect of side chains on hydrothermal stability. Journal of Physical Chemistry A, 2003, 107(31): 5987–5992

[112] Klingler D , Berg J , Vogel H . Hydrothermal reactions of alanine and glycine in sub- and supercritical water. Journal of Supercritical Fluids, 2007, 43(1): 112–119

[113] Chen Y P , Huang Y Q , Xie J J , Yin X L , Wu C Z . Hydrothermal reaction of phenylalanine as a model compound of algal protein. Journal of Fuel Chemistry & Technology, 2014, 42(1): 61–67

[114] Torrens-Spence M P , Liu P , Ding H , Harich K , Gillaspy G , Li J . Biochemical evaluation of the decarboxylation and decarboxylation-deamination activities of plant aromatic amino acid decarboxylases. Journal of Biological Chemistry, 2013, 288(4): 2376–2387

[115] Iqubal M A , Sharma R , Jheeta S . Kamaluddin. Thermal condensation of glycine and alanine on metal ferrite surface: primitive peptide bond formation scenario. Life, 2017, 7(2): 15

[116] Otake T , Taniguchi T , Furukawa Y , Kawamura F , Nakazawa H , Kakegawa T . Stability of amino acids and their oligomerization under high-pressure conditions: implications for prebiotic chemistry. Astrobiology, 2011, 11(8): 799–813

[117] Pedreira-Segade U , Hao J , Montagnac G , Cardon H , Daniel I . Spontaneous polymerization of glycine under hydrothermal conditions. ACS Earth & Space Chemistry, 2019, 3(8): 1669–1677

[118] Hodge J E . Dehydrated foods, chemistry of browning reactions in model systems. Journal of Agricultural and Food Chemistry, 1953, 1(15): 928–943

[119] Martins S I F S , Jongen W M F , van Boekel M A J S . A review of Maillard reaction in food and implications to kinetic modelling. Trends in Food Science & Technology, 2000, 11(9): 364–373

[120] Li J , Brill T B . Spectroscopy of hydrothermal reactions, part 26: kinetics of decarboxylation of aliphatic amino acids and comparison with the rates of racemization. International Journal of Chemical Kinetics, 2003, 35(11): 602–610

[121] Ueno S , Ichinoi H , Zhao J , Fujii T . Degradation of fish gelatin using hot-compressed water and the properties of the degradation products. High Pressure Research, 2015, 35(2): 203–213

[122] Sohn M , Ho C T . Ammonia generation during thermal degradation of amino acids. Journal of Agricultural and Food Chemistry, 1995, 43(12): 3001–3003

[123] Bella D L , Hahn C , Stipanuk M H . Effects of nonsulfur and sulfur amino acids on the regulation of hepatic enzymes of cysteine metabolism. American Journal of Physiology. Endocrinology and Metabolism, 1999, 277(1): E144–E153

[124] Stipanuk M H , Dominy J E Jr , Lee J I , Coloso R M . Mammalian cysteine metabolism: new insights into regulation of cysteine metabolism. Journal of Nutrition, 2006, 136(6): 1652S–1659S

[125] Kwon Y H , Stipanuk M H . Cysteine regulates expression of cysteine dioxygenase and γ-glutamylcysteine synthetase in cultured rat hepatocytes. American Journal of Physiology. Endocrinology and Metabolism, 2001, 280(5): E804–E815

[126] Courtney-MartinGPencharzP B. Sulfur amino acids metabolism from protein synthesis to glutathione. In: The Molecular Nutrition of Amino Acids and Proteins. Dardevet D, ed. Boston: Academic Press, 2016, 265–286

[127] Kovacs J , Holleran E M , Hui K Y . Kinetic studies in peptide chemistry. Coupling, racemization and evaluation of methods useful for shortening coupling time. Journal of Organic Chemistry, 1980, 45(6): 1060–1065

[128] Fujimaki M , Kato S , Kurata T . Pyrolysis of sulfur-containing amino acids. Agricultural and Biological Chemistry, 1969, 33(8): 1144–1151

[129] Nagano Y , Samejima H , Kinoshita S . Antioxidant activity of 3-methylthiopropylamine hydrochloride. Agricultural and Biological Chemistry, 1968, 32(7): 846–850

[130] Samanmulya T , Farobie O , Matsumura Y . Gasification characteristics of histidine and 4-methylimidazole under supercritical water conditions. Biomass Conversion and Biorefinery, 2017, 7(4): 487–494

[131] De Schouwer F , Claes L , Vandekerkhove A , Verduyckt J , De Vos D E . Protein-rich biomass waste as a resource for future biorefineries: state of the art, challenges, and opportunities. ChemSusChem, 2019, 12(7): 1272–1303

[132] Kourist R , Guterl J K , Miyamoto K , Sieber V . Enzymatic decarboxylation: an emerging reaction for chemicals production from renewable resources. ChemCatChem, 2014, 6(3): 689–701

[133] Yamano N , Kawasaki N , Takeda S , Nakayama A . Production of 2-pyrrolidone from biobased glutamate by using Escherichia coli. Journal of Polymers and the Environment, 2013, 21(2): 528–533

[134] Teng Y , Scott E L , Witte-van Dijk S C M , Sanders J P M . Simultaneous and selective decarboxylation of l-serine and deamination of l-phenylalanine in an amino acid mixture—a means of separating amino acids for synthesizing biobased chemicals. New Biotechnology, 2016, 33(1): 171–178

[135] Egorova K S , Seitkalieva M M , Posvyatenko A V , Ananikov V P . An unexpected increase of toxicity of amino acid-containing ionic liquids. Toxicology Research, 2015, 4(1): 152–159

[136] Spekreijse J , Le Nôtre J , van Haveren J , Scott E L , Sanders J P M . Simultaneous production of biobased styrene and acrylates using ethenolysis. Green Chemistry, 2012, 14(10): 2747–2751

[137] Claes L , Janssen M , De Vos D E . Organocatalytic decarboxylation of amino acids as a route to bio-based amines and amides. ChemCatChem, 2019, 11(17): 4297–4306

[138] Chatelus G . Thermal decarboxylation of α-amino acids. Bulletin de la Société Chimique de France, 1964, 10(1): 2523–2532

[139] Hartmann M , Seiberth M . Über ein tetralin-peroxyd. Helvetica Chimica Acta, 1932, 15(1): 1390–1392

[140] Kumar R , Shah S , Paramita Das P , Bhagavanbhai G G K , Al Fatesh A , Chowdhury B . An overview of caprolactam synthesis. Catalysis Reviews. Science and Engineering, 2019, 61(4): 516–594

[141] FrostJ W. Catalytic deamination for caprolactam production. US Patent, US8283466B2, 2012

[142] FrostJ W. Synthesis of caprolactam from lysine. US Patent, US7399855B2, 2008

[143] De Schouwer F , Cuypers T , Claes L , De Vos D E . Metal-catalyzed reductive deamination of glutamic acid to bio-based dimethyl glutarate and methylamines. Green Chemistry, 2017, 19(8): 1866–1876

[144] Weiss I M , Muth C , Drumm R , Kirchner H O K . Thermal decomposition of the amino acids glycine, cysteine, aspartic acid, asparagine, glutamic acid, glutamine, arginine and histidine. BMC Biophysics, 2018, 11(1): 2

[145] Mazlan M A F , Uemura Y , Osman N , Suzana Y . Fast pyrolysis of hardwood residues using a fixed bed drop-type pyrolyzer. Energy Conversion and Management, 2015, 98(1): 208–214

[146] Mullen C , Boateng A , Goldberg N , Lima I , Laird D , Hicks K . Bio-oil and bio-char production from corn cobs and stover by fast pyrolysis. Biomass and Bioenergy, 2010, 34(1): 67–74

[147] Su H , Xu G , Chen H , Xu Y . Enriching duckweed as an energy crop for producing biobutanol using enzyme hydrolysis pretreatments and strengthening fermentation process using pH-stat. ACS Sustainable Chemistry & Engineering, 2015, 3(1): 2002

[148] Liu G , Wright M M , Zhao Q , Brown R C , Wang K , Xue Y . Catalytic pyrolysis of amino acids: comparison of aliphatic amino acid and cyclic amino acid. Energy Conversion and Management, 2016, 112(1): 220–225

[149] Li J , Wang Z , Yang X , Hu L , Liu Y , Wang C . Decomposing or subliming? An investigation of thermal behavior of L-leucine. Thermochimica Acta, 2006, 447(1): 147–153

[150] Kitagawa H , Sendoda Y , Ono Y . Transformation of propane into aromatic hydrocarbons over ZSM-5 zeolites. Journal of Catalysis, 1986, 101(1): 12–18

[151] Ono Y , Kitagawa H , Sendoda Y . Transformation of but-1-ene into aromatic hydrocarbons over ZSM-5 zeolites. Journal of the Chemical Society, Faraday Transactions 1. Physical Chemistry in Condensed Phases, 1987, 83(9): 2913–2923

[152] Sharma R , Chan W G , Seeman J , Hajaligol M . Formation of low molecular weight heterocycles and polycyclic aromatic compounds (PACs) in the pyrolysis of α-amino acids. Journal of Analytical and Applied Pyrolysis, 2003, 66(1): 97–121

[153] Wang K , Brown R . Catalytic pyrolysis of corn dried distillers grains with solubles to produce hydrocarbons. ACS Sustainable Chemistry & Engineering, 2014, 2(1): 2142–2148

[154] Wang K , Kim K H , Brown R C . Catalytic pyrolysis of individual components of lignocellulosic biomass. Green Chemistry, 2014, 16(2): 727–735

[155] Wang K , Brown R C . Catalytic pyrolysis of microalgae for production of aromatics and ammonia. Green Chemistry, 2013, 15(3): 675–681

[156] Zhang H , Cheng Y T , Vispute T P , Xiao R , Huber G W . Catalytic conversion of biomass-derived feedstocks into olefins and aromatics with ZSM-5: the hydrogen to carbon effective ratio. Energy & Environmental Science, 2011, 4(6): 2297–2307

[157] Carlson T R , Jae J , Lin Y C , Tompsett G A , Huber G W . Catalytic fast pyrolysis of glucose with HZSM-5: the combined homogeneous and heterogeneous reactions. Journal of Catalysis, 2010, 270(1): 110–124

[158] Lien Y C , Nawar W W . Thermal decomposition of some amico acids: alanine and β-alanine. Journal of Food Science, 1974, 39(5): 914–916

[159] Tian Y , Zhang J , Zuo W , Chen L , Cui Y , Tan T . Nitrogen conversion in relation to NH₃ and HCN during microwave pyrolysis of sewage sludge. Environmental Science & Technology, 2013, 47(7): 3498–3505

[160] Yuan S , Zhou Z J , Li J , Wang F C . Nitrogen conversion during rapid pyrolysis of coal and petroleum coke in a high-frequency furnace. Applied Energy, 2012, 92(1): 854–859

[161] Li M , Zhao Y , Guo Q , Qian X , Niu D . Bio-hydrogen production from food waste and sewage sludge in the presence of aged refuse excavated from refuse landfill. Renewable Energy, 2008, 33(12): 2573–2579

[162] Gomez-Flores M , Nakhla G , Hafez H . Microbial kinetics of Clostridium termitidis on cellobiose and glucose for biohydrogen production. Biotechnology Letters, 2015, 37(10): 1965–1971

[163] Cheng J , Ding L , Lin R , Liu M , Zhou J , Cen K . Physicochemical characterization of typical municipal solid wastes for fermentative hydrogen and methane co-production. Energy Conversion and Management, 2016, 117(1): 297–304

[164] Ionescu G , Rada E , Ragazzi M , Mărculescu C , Badea A , Apostol T . Integrated municipal solid waste scenario model using advanced pretreatment and waste to energy processes. Energy Conversion and Management, 2013, 76(1): 1083–1092

[165] Sharma P , Melkania U . Enhancement effect of amino acids on hydrogen production from organic fraction of municipal solid waste using co-culture of Escherichia coli and Enterobacter aerogenes. Energy Conversion and Management, 2018, 163(1): 260–267

[166] Xia A , Cheng J , Ding L , Lin R , Song W , Su H , Zhou J , Cen K . Substrate consumption and hydrogen production via co-fermentation of monomers derived from carbohydrates and proteins in biomass wastes. Applied Energy, 2015, 139(1): 9–16

[167] Cheng J , Song W , Xia A , Su H , Zhou J , Cen K . Sequential generation of hydrogen and methane from xylose by two-stage anaerobic fermentation. International Journal of Hydrogen Energy, 2012, 37(1): 13323–13329

[168] Chen Y , Xiao N , Zhao Y , Mu H . Enhancement of hydrogen production during waste activated sludge anaerobic fermentation by carbohydrate substrate addition and pH control. Bioresource Technology, 2012, 114(1): 349–356

[169] Su H , Cheng J , Zhou J , Song W , Cen K . Combination of dark- and photo-fermentation to enhance hydrogen production and energy conversion efficiency. International Journal of Hydrogen Energy, 2009, 34(1): 8846–8853

[170] Junghare M , Subudhi S , Lal B . Improvement of hydrogen production under decreased partial pressure by newly isolated alkaline tolerant anaerobe, Clostridium butyricum TM-9A: optimization of process parameters. International Journal of Hydrogen Energy, 2012, 37(1): 3160–3168

[171] Lo Y C , Lu W C , Chen C Y , Chang J S . Dark fermentative hydrogen production from enzymatic hydrolysate of xylan and pretreated rice straw by Clostridium butyricum CGS5. Bioresource Technology, 2010, 101(15): 5885–5891

[172] Xia A , Cheng J , Lin R , Liu J , Zhou J , Cen K . Sequential generation of hydrogen and methane from glutamic acid through combined photo-fermentation and methanogenesis. Bioresource Technology, 2013, 131(1): 146–151

[173] Yuan Z , Yang H , Zhi X , Shen J . Enhancement effect of L-cysteine on dark fermentative hydrogen production. International Journal of Hydrogen Energy, 2008, 33(22): 6535–6540

[174] Elbeshbishy E , Hafez H , Nakhla G . Ultrasonication for biohydrogen production from food waste. International Journal of Hydrogen Energy, 2011, 36(4): 2896–2903

[175] Xia A , Cheng J , Ding L , Lin R , Song W , Zhou J , Cen K . Effects of changes in microbial community on the fermentative production of hydrogen and soluble metabolites from Chlorella pyrenoidosa biomass in semi-continuous operation. Energy, 2014, 68(1): 982–988

[176] Chen H , Xie Y , Chen W , Xia M , Li K , Chen Z , Chen Y , Yang H . Investigation on co-pyrolysis of lignocellulosic biomass and amino acids using TG-FTIR and Py-GC/MS. Energy Conversion and Management, 2019, 196(1): 320–329

[177] BrittPBuchananA COwensCSkeenJ. Does glucose enhance the formation of nitrogen containing polycyclic aromatic compounds and polycyclic aromatic hydrocarbons in the pyrolysis of proline? Fuel, 2004, 83(12): 1417–1432

[178] Huber G W , Iborra S , Corma A . Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering. Chemical Reviews, 2006, 106(9): 4044–4098

[179] Yang H , Huan B , Chen Y , Gao Y , Li J , Chen H . Biomass-based pyrolytic polygeneration system for bamboo industry waste: evolution of the char structure and the pyrolysis mechanism. Energy & Fuels, 2016, 30(8): 6430–6439

[180] Choi S S , Ko J E . Analysis of cyclic pyrolysis products formed from amino acid monomer. Journal of Chromatography. A, 2011, 1218(46): 8443–8455

[181] Sharma R , Chan W , Hajaligol M . Product compositions from pyrolysis of some aliphatic α-amino acids. Journal of Analytical and Applied Pyrolysis, 2006, 75(2): 69–81

[182] Ren Q , Zhao C . NO_x and N₂O precursors from biomass pyrolysis: nitrogen transformation from amino acid. Environmental Science & Technology, 2012, 46(7): 4236–4240

[183] Chiavari G , Galletti G C . Pyrolysis—gas chromatography/mass spectrometry of amino acids. Journal of Analytical and Applied Pyrolysis, 1992, 24(2): 123–137

Competing interests

The authors declare that they have no competing interests.

Acknowledgements

Authors acknowledges a generous funding from the National Water and Energy Center at the United Arab Emirates University (UAEU) through the 12R124 grant.

RIGHTS & PERMISSIONS

2024 Higher Education Press