Co-Immobilization of a Multi-Enzyme Cascade: (S)-Selective Amine Transaminases, l-Amino Acid Oxidase and Catalase.
apremilast
biocatalysis
chiral amines
recycling
substrate channeling
Journal
Chembiochem : a European journal of chemical biology
ISSN: 1439-7633
Titre abrégé: Chembiochem
Pays: Germany
ID NLM: 100937360
Informations de publication
Date de publication:
04 10 2023
04 10 2023
Historique:
revised:
26
06
2023
received:
06
06
2023
medline:
23
10
2023
pubmed:
27
6
2023
entrez:
27
6
2023
Statut:
ppublish
Résumé
An enzyme cascade was established previously consisting of a recycling system with an l-amino acid oxidase (hcLAAO4) and a catalase (hCAT) for different α-keto acid co-substrates of (S)-selective amine transaminases (ATAs) in kinetic resolutions of racemic amines. Only 1 mol % of the co-substrate was required and l-amino acids instead of α-keto acids could be applied. However, soluble enzymes cannot be reused easily. Immobilization of hcLAAO4, hCAT and the (S)-selective ATA from Vibrio fluvialis (ATA-Vfl) was addressed here. Immobilization of the enzymes together rather than on separate beads showed higher reaction rates most likely due to fast co-substrate channeling between ATA-Vfl and hcLAAO4 due to their close proximity. Co-immobilization allowed further reduction of the co-substrate amount to 0.1 mol % most likely due to a more efficient H
Identifiants
pubmed: 37368451
doi: 10.1002/cbic.202300425
doi:
Substances chimiques
Amines
0
Transaminases
EC 2.6.1.-
L-Amino Acid Oxidase
EC 1.4.3.2
Enzymes, Immobilized
0
Catalase
EC 1.11.1.6
Keto Acids
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300425Informations de copyright
© 2023 The Authors. ChemBioChem published by Wiley-VCH GmbH.
Références
U. T. Bornscheuer, G. W. Huisman, R. J. Kazlauskas, S. Lutz, J. C. Moore, K. Robins, Nature 2012, 485, 185.
M. D. Truppo, ACS Med. Chem. Lett. 2017, 8, 476.
U. T. Bornscheuer, Phil. Trans. R. Soc. A 2018, 376, 20170063.
E. M. M. Abdelraheem, H. Busch, U. Hanefeld, F. Tonin, React. Chem. Eng. 2019, 4, 1878.
A. Schmid, J. S. Dordick, B. Hauer, A. Kiener, M. Wubbolts, B. Witholt, Nature 2001, 409, 258.
H. E. Schoemaker, D. Mink, M. G. Wubbolts, Science 2003, 299, 1694.
P. Tripathi, S. Sinha, Curr. Sustain. Renew. Ener. 2020, 7, 66.
J. D. Rozzell, Bioorg. Med. Chem. 1999, 7, 2253;
M. Breuer, K. Ditrich, T. Habicher, B. Hauer, M. Kesseler, R. Stürmer, T. Zelinski, Angew. Chem. Int. Ed. 2004, 43, 788.
P. Anastas, N. Eghbali, Chem. Soc. Rev. 2010, 39, 301;
R. A. Sheldon, J. M. Woodley, Chem. Rev. 2018, 118, 801;
T. E. Graedel, Handbook of Green Chemistry and Technology (Hrsg. J. H. Clark, D. Macquarrie), Blackwell Science Ltd, Oxford, UK, 2002, p. 56-61.
E. Ricca, B. Brucher, J. H. Schrittwieser, Adv. Synth. Catal. 2011, 353, 2239.
H.-S. Bae, S.-G. Lee, S.-P. Hong, M.-S. Kwak, N. Esaki, K. Soda, M.-H. Sung, J. Mol. Catal. B 1999, 6, 241;
S. Faure, A. A. Jensen, V. Maurat, X. Gu, E. Sagot, D. J. Aitken, J. Bolte, T. Gefflaut, L. Bunch, J. Med. Chem. 2006, 49, 6532;
M. Xian, S. Alaux, E. Sagot, T. Gefflaut, J. Org. Chem. 2007, 72, 7560.
C. V. Voss, C. C. Gruber, K. Faber, T. Knaus, P. Macheroux, W. Kroutil, J. Am. Chem. Soc. 2008, 130, 13969;
C. V. Voss, C. C. Gruber, W. Kroutil, Angew. Chem. Int. Ed. 2008, 47, 741.
I. G. Fotheringham, N. Grinter, D. P. Pantaleone, R. F. Senkpeil, P. P. Taylor, Bioorg. Med. Chem. 1999, 7, 2209;
M. D. Truppo, J. D. Rozzell, N. J. Turner, Org. Process Res. Dev. 2010, 14, 234.
M. Höhne, S. Kühl, K. Robins, U. T. Bornscheuer, ChemBioChem 2008, 9, 363.
M. Česnik Katulić, M. Sudar, K. Hernández, Y. Qi, S. J. Charnock, Đ. Vasić-Rački, P. Clapés, Z. Findrik Blažević, Ind. Eng. Chem. Res. 2021, 60, 13846.
N. Alcover, G. Álvaro, M. Guillén, Catalysts 2021, 11, 973.
T. Heinks, J. Paulus, S. Koopmeiners, T. Beuel, N. Sewald, M. Höhne, U. T. Bornscheuer, G. Fischer von Mollard, ChemBioChem 2022, 23, e202200329.
S. Bloess, T. Beuel, T. Krüger, N. Sewald, T. Dierks, G. Fischer von Mollard, Appl. Microbiol. Biotechnol. 2019, 103, 2229.
M. C. Heß, S. Bloess, J. M. Risse, K. Friehs, G. Fischer von Mollard, MicrobiologyOpen 2020, 9, e1112.
P. Macheroux, O. Seth, C. Bollschweiler, M. Schwarz, M. Kurfürst, L.-C. Au, S. Ghisla, Eur. J. Biochem. 2001, 268, 1679.
L. Pollegioni, P. Motta, G. Molla, Appl. Microbiol. Biotechnol. 2013, 97, 9323.
A. Perera, H. G. Parkes, H. Herz, P. Haycock, D. R. Blake, M. C. Grootveld, Free Radical Res. 1997, 26, 145;
A. Lopalco, G. Dalwadi, S. Niu, R. L. Schowen, J. Douglas, V. J. Stella, J. Pharm. Sci. 2016, 105, 705.
S. Wu, R. Snajdrova, J. C. Moore, K. Baldenius, U. T. Bornscheuer, Angew. Chem. Int. Ed. 2021, 60, 88.
H.-S. Bea, S.-H. Lee, H. Yun, Biotechnol. Bioprocess Eng. 2011, 16, 291.
P. P. Taylor, D. P. Pantaleone, R. F. Senkpeil, I. G. Fotheringham, Trends Biotechnol. 1998, 16, 412;
O. Buß, M. Voss, A. Delavault, P. Gorenflo, C. Syldatk, U. Bornscheuer, J. Rudat, Molecules 2018, 23, 1211.
C. Schmidt-Dannert, F. Lopez-Gallego, Microb. Biotechnol. 2016, 9, 601.
M. D. Truppo, H. Strotman, G. Hughes, ChemCatChem 2012, 4, 1071.
N. Kaličanin, G. Kovačević, M. Spasojević, O. Prodanović, S. Jovanović-Šanta, D. Škorić, D. Opsenica, R. Prodanović, Process Biochem. 2022, 121, 674.
R. C. Rodrigues, C. Ortiz, Á. Berenguer-Murcia, R. Torres, R. Fernández-Lafuente, Chem. Soc. Rev. 2013, 42, 6290.
Z. Molnár, E. Farkas, Á. Lakó, B. Erdélyi, W. Kroutil, B. G. Vértessy, C. Paizs, L. Poppe, Catalysts 2019, 9, 438;
W. Böhmer, T. Knaus, A. Volkov, T. K. Slot, N. R. Shiju, K. Engelmark Cassimjee, F. G. Mutti, J. Biotechnol. 2019, 291, 52.
T. Heinks, N. Montua, M. Teune, J. Liedtke, M. Höhne, U. T. Bornscheuer, G. Fischer von Mollard, Catalysts 2023, 13, 300.
J.-R. Cao, F.-F. Fan, C.-J. Lv, H.-P. Wang, Y. Li, S. Hu, W.-R. Zhao, H.-B. Chen, J. Huang, L.-H. Mei, Front. Chem. 2021, 9, 664156.
S. Velasco-Lozano, E. Jackson, M. Ripoll, F. López-Gallego, L. Betancor, Int. J. Biol. Macromol. 2020, 164, 4318.
H. Jia, F. Huang, Z. Gao, C. Zhong, H. Zhou, M. Jiang, P. Wei, Biotechnol. Rep. 2016, 10, 49.
J. Fu, Y. R. Yang, A. Johnson-Buck, M. Liu, Y. Liu, N. G. Walter, N. W. Woodbury, H. Yan, Nat. Nanotechnol. 2014, 9, 531;
X. Huang, H. M. Holden, F. M. Raushel, Annu. Rev. Biochem. 2001, 70, 149;
D. P. Patterson, B. Schwarz, R. S. Waters, T. Gedeon, T. Douglas, ACS Chem. Biol. 2014, 9, 359;
C. You, Y.-H. P. Zhang, ACS Synth. Biol. 2013, 2, 102;
I. Wheeldon, S. D. Minteer, S. Banta, S. C. Barton, P. Atanassov, M. Sigman, Nat. Chem. 2016, 8, 299;
H. O. Spivey, J. Ovádi, Methods 1999, 19, 306.
D. Świętochowska, A. Łochowicz, N. Ocal, L. Pollegioni, F. Charmantray, L. Hecquet, K. Szymańska, Catalysts 2023, 13, 95.
D. Barreca, G. Neri, A. Scala, E. Fazio, D. Gentile, A. Rescifina, A. Piperno, Biomater. Sci. 2018, 6, 3231;
K. Erol, B. K. Cebeci, K. Köse, D. A. Köse, Int. J. Biol. Macromol. 2019, 123, 738;
G. Görenek, E. Akyilmaz, E. Dinçkaya, Artif. Cells Blood Substitutes Biotechnol. 2004, 32, 453;
A. G. Grigoras, Biochem. Eng. J. 2017, 117, 1.
R. M. El-Shishtawy, N. S. E. Ahmed, Y. Q. Almulaiky, Catalysts 2021, 11, 820.
J. Kaushal, Seema, G. Singh, S. K. Arya, Biotechnol. Rep. 2018, 18, e00258.
L. Betancor, A. Hidalgo, G. Fernández-Lorente, C. Mateo, V. Rodríguez, M. Fuentes, F. López-Gallego, R. Fernández-Lafuente, J. M. Guisan, Biotechnol. Prog. 2003, 19, 784;
J. M. Bolivar, B. Nidetzky, Biotechnol. Bioeng. 2012, 109, 1490;
Y. Bu, L. Hu, W. Feng, ACS Appl. Nano Mater. 2021, 4, 12373;
D. Carballares, R. Fernandez-Lafuente, J. Rocha-Martin, Process Biochem. 2022, 122, 120;
P. T. Dang, H. G. Le, V.-T. Hoang, H. T. H. Tran, C. D. Dao, K. T. Nguyen, G. H. Le, Q. K. Nguyen, T. V. Nguyen, T. A. Vu, J. Nanosci. Nanotechnol. 2017, 17, 947;
I. Dib, B. Nidetzky, BMC Biotechnol. 2008, 8, 72;
F. López-Gallego, L. Betancor, A. Hidalgo, N. Alonso, G. Fernandez-Lorente, J. M. Guisan, R. Fernandez-Lafuente, Enzyme Microb. Technol. 2005, 37, 750;
K. Parkin, H. O. Hultin, Biotechnol. Bioeng. 1979, 21, 939;
E.-M. Trost, L. Fischer, J. Mol. Catal. B 2002, 19 (20), 189;
M. Wang, W. Qi, H. Xu, H. Yu, S. Zhang, Z. Shen, J. Ind. Microbiol. Biotechnol. 2019, 46, 1461.
J. Sun, K. Du, X. Song, Q. Gao, H. Wu, J. Ma, P. Ji, W. Feng, Green Chem. 2015, 17, 4465.
K.-S. Wong, W.-P. Fong, P. W.-K. Tsang, Eng. Life Sci. 2011, 11, 491.
S. Butò, L. Pollegioni, L. D'Angiuro, M. S. Pilone, Biotechnol. Bioeng. 1994, 44, 1288;
Z. Findrik, Chem. Biochem. Eng. Q. 2016, 30, 93;
R. Li, J. Sun, Y. Fu, K. Du, M. Cai, P. Ji, W. Feng, Catalysts 2016, 6, 66;
R. Upadhya, Nagajyothi, S. G. Bhat, Biotechnol. Bioeng. 2000, 68, 430.
R. Fernández-Lafuente, V. Rodriguez, J. M. Guisán, Enzyme Microb. Technol. 1998, 23, 28.
S. Lata, C. S. Pundir, Int. J. Biol. Macromol. 2013, 54, 250;
Y. C. LEE, M. H. HUH, J. Food Biochem. 1999, 23, 173;
L. Wu, X. Guo, G. Wu, P. Liu, Z. Liu, R. Soc. Open Sci. 2019, 6, 182035;
M. Yadav, P. Singh, Vegetos 2022, 35, 10.1007/s42535-022-00457-5s;
P. D'Arrigo, C. Allegretti, A. Fiorati, L. Piubelli, E. Rosini, D. Tessaro, M. Valentino, L. Pollegioni, Catal. Sci. Technol. 2015, 5, 1106.
G. S. Hossain, J. Li, H. Shin, G. Du, L. Liu, J . Chen, Appl. Microbiol. Biotechnol. 2014, 98, 1507.
A. A. Halim, N. Szita, F. Baganz, J. Biotechnol. 2013, 168, 567;
S. Matosevic, G. J. Lye, F. Baganz, J. Biotechnol. 2011, 155, 320;
L. Nagy-Győr, E. Abaházi, V. Bódai, P. Sátorhelyi, B. Erdélyi, D. Balogh-Weiser, C. Paizs, G. Hornyánszky, L. Poppe, ChemBioChem 2018, 19, 1845.
T. Dierks, M. R. Lecca, P. Schlotterhose, B. Schmidt, K. von Figura, EMBO J. 1999, 18, 2084;
J. Peng, S. Alam, K. Radhakrishnan, M. Mariappan, M. G. Rudolph, C. May, T. Dierks, K. von Figura, B. Schmidt, FEBS J. 2015, 282, 3262.
C. Xiang, S. Wu, U. T. Bornscheuer, Bioorg. Med. Chem. 2021, 43, 116271.
J. Sun, W.-H. Cui, K. Du, Q. Gao, M. Du, P. Ji, W. Feng, J. Biotechnol. 2017, 245, 14.
H. Brundiek, M. Höhne, Applied Biocatalysis: From Fundamental Science to Industrial Applications (Hrsg. L. Hilterhaus, A. Liese, U. Kettling, G. Antranikian), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 2016, p. 199-218;
N. Richter, J. E. Farnberger, D. Pressnitz, H. Lechner, F. Zepeck, W. Kroutil, Green Chem. 2015, 17, 2952;
I. Slabu, J. L. Galman, R. C. Lloyd, N. J. Turner, ACS Catal. 2017, 7, 8263.
M. D. Truppo, N. J. Turner, J. D. Rozzell, Chem. Commun. 2009, 2127.
D. Koszelewski, D. Pressnitz, D. Clay, W. Kroutil, Org. Lett. 2009, 11, 4810.
K. Du, R. Li, D. Zhang, W. Feng, ChemBioChem 2019, 20, 701.
T. Börner, S. Rämisch, E. R. Reddem, S. Bartsch, A. Vogel, A.-M. W. H. Thunnissen, P. Adlercreutz, C. Grey, ACS Catal. 2017, 7, 1259;
S. Chen, H. Land, P. Berglund, M. S. Humble, J. Mol. Catal. B 2016, 124, 20;
J.-S. Shin, H. Yun, J.-W. Jang, I. Park, B.-G. Kim, Appl. Microbiol. Biotechnol. 2003, 61, 463.
F. Belov, A. Mildner, T. Knaus, F. G. Mutti, J. von Langermann, React. Chem. Eng. 2023;
D. Hülsewede, J.-N. Dohm, J. von Langermann, Adv. Synth. Catal. 2019, 361, 2727 ;
J. Neuburger, F. Helmholz, S. Tiedemann, P. Lehmann, P. Süss, U. Menyes, J. von Langermann, Chem. Eng. Process. 2021, 168, 108578.
E. Başak, T. Aydemir, Artif. Cells, Nanomed., Biotechnol. 2013, 41, 269.
J.-S. Shin, B.-G. Kim, Biotechnol. Bioeng. 1998, 60, 534;
J. S. Shin, B. G. Kim, Biosci. Biotechnol. Biochem. 2001, 65, 1782.
I. V. Pavlidis, M. S. Weiß, M. Genz, P. Spurr, S. P. Hanlon, B. Wirz, H. Iding, U. T. Bornscheuer, Nat. Chem. 2016, 8, 1076.
N. Janson, T. Heinks, T. Beuel, S. Alam, M. Höhne, U. T. Bornscheuer, G. Fischer von Mollard, N. Sewald, ChemCatChem 2022, 14.
S. Schätzle, M. Höhne, E. Redestad, K. Robins, U. T. Bornscheuer, J. Anal. Chem. 2009, 81, 8244.
A. van Boven, P. S. T. Tan, W. N. Konings, Appl. Environ. Microbiol. 1988, 54, 43.
D. Brugger, I. Krondorfer, K. Zahma, T. Stoisser, J. M. Bolivar, B. Nidetzky, C. K. Peterbauer, D. Haltrich, Biotechnol. J. 2014, 9, 474.