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Biocatalytic Decarboxylation of Aromatic l-Amino Acids with In Situ Removal of Both Products for Enhanced Production of Biogenic Amines

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Abstract

Biogenic amines are important messengers in neurotransmission, drawing attention to pharmaceutical applications. Here, we developed a novel biocatalytic process for the preparation of biogenic amines using aromatic l-amino acid decarboxylase (AADC) under an in situ product removal (ISPR) condition. The AADC from Bacillus atrophaeus (AADC-BA) showed broad substrate specificity for aromatic amino acids, affording > 90% conversions of 10 mM substrates to corresponding products: 2-phenylethylamine (2-PEA), tryptamine, serotonin, and dopamine. Owing to enzyme inhibitions by the reaction products, we implemented an ISPR strategy using a cation exchange resin and an open reactor system for removal of amine and CO2, respectively. Under the open-air conditions, the addition of Dowex 50WX8 afforded 81% conversion of 100 mM l-phenylalanine to 2-PEA within 1 h, whereas 56% conversion was obtained without the resin. The ISPR strategy enabled the preparative-scale production of serotonin from 5-hydroxy-l-tryptophan (405 mg), yielding > 99% conversion within 40 min.

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References

  1. Ng J, Papandreou A, Heales SJ, Kurian MA (2015) Nat Rev Neurol 11:567–584

    Article  CAS  Google Scholar 

  2. Khan MZ, Nawaz W (2016) Biomed Pharmacother 83:439–449

    Article  CAS  Google Scholar 

  3. Berry MD, Gainetdinov RR, Hoener MC, Shahid M (2017) Pharmacol Ther 180:161–180

    Article  CAS  Google Scholar 

  4. Jesulola E, Micalos P, Baguley IJ (2018) Behav Brain Res 341:79–90

    Article  CAS  Google Scholar 

  5. Shimazu S, Miklya I (2004) Prog Neuro-Psychopharmacol Biol Psychiatry 28:421–427

    Article  CAS  Google Scholar 

  6. Sánchez-Jiménez F, Ruiz-Pérez MV, Urdiales JL, Medina MA (2013) Br J Pharmacol 170:4–16

    Article  Google Scholar 

  7. Frederick AL, Stanwood GD (2009) Dev Neurosci 31:7–22

    Article  CAS  Google Scholar 

  8. Serra S, Fuganti C, Brenna E (2005) Trends Biotechnol 23:193–198

    Article  CAS  Google Scholar 

  9. Ali S, Nawaz W (2016) Appl Biochem Biotechnol 179:1435–1444

    Article  CAS  Google Scholar 

  10. Park S, Kang K, Lee SW, Ahn M-J, Bae J-M, Back K (2011) Appl Microbiol Biotechnol 89:1387–1394

    Article  CAS  Google Scholar 

  11. Zhang H, Lu Y, Wu S, Wei Y, Liu Q, Liu J, Jiao Q (2016) J Mol Catal B Enzym 124:38–44

    Article  CAS  Google Scholar 

  12. Anderson WA, Moo-Young M, Legge RL (1992) Biotechnol Bioeng 39:781–789

    Article  CAS  Google Scholar 

  13. Zhu MY, Juorio AV (1995) Gen Pharmacol 26:681–696

    Article  CAS  Google Scholar 

  14. Berry MD, Juorio AV, Li XM, Boulton AA (1996) Neurochem Res 21:1075–1087

    Article  CAS  Google Scholar 

  15. Sáenz-De-Miera LE, Ayala FJ (2004) J Evol Biol 17:55–66

    Article  Google Scholar 

  16. Burchett SA, Hicks TP (2006) Prog Neurobiol 79:223–246

    Article  CAS  Google Scholar 

  17. Manegold C, Hoffmann GF, Degen I, Ikonomidou H, Knust A, Laaß MW, Pritsch M, Wilichowski E, Hörster F (2009) J Inherit Metab Dis 32:371–380

    Article  CAS  Google Scholar 

  18. D’Este M, Alvarado-Morales M, Angelidaki I (2018) Biotechnol Adv 36:14–25

    Article  Google Scholar 

  19. Wang H, Liu W, Shi F, Huang L, Lian J, Qu L, Cai J, Xu Z (2018) Metab Eng 48:279–287

    Article  CAS  Google Scholar 

  20. Fordjour E, Adipah FK, Zhou S, Du G, Zhou J (2019) Microb Cell Fact 18:74

    Article  Google Scholar 

  21. Li T, Huo L, Pulley C, Liu A (2012) Bioorg Chem 43:2–14

    Article  CAS  Google Scholar 

  22. Park E-S, Shin J-S (2011) Enzyme Microb Technol 49:380–387

    Article  CAS  Google Scholar 

  23. Han S-W, Shin J-S (2016) J Mol Catal B Enzym 133:S500–S507

    Article  Google Scholar 

  24. Yuwen L, Zhang F-L, Chen Q-H, Lin S-J, Zhao Y-L, Li Z-Y (2013) Sci Rep 3:1753

    Article  Google Scholar 

  25. Zhang K, Ni Y (2014) Protein Expr Purif 94:33–39

    Article  CAS  Google Scholar 

  26. Kezmarsky ND, Xu H, Graham DE, White RH (2005) Biochim Biophys Acta Gen Subj 1722:175–182

    Article  CAS  Google Scholar 

  27. Kalb D, Gressler J, Hoffmeister D (2016) ChemBioChem 17:132–136

    Article  CAS  Google Scholar 

  28. Labrou NE, Clonis YD (1999) Arch Biochem Biophys 365:17–24

    Article  CAS  Google Scholar 

  29. Jung DH, Choi W, Choi KY, Jung E, Yun H, Kazlauskas RJ, Kim BG (2013) Appl Microbiol Biotechnol 97:1501–1511

    Article  CAS  Google Scholar 

  30. Dimroth P, Thomer A (1986) Eur J Biochem 156:157–162

    Article  CAS  Google Scholar 

  31. Black BC, Smarrelli J (1986) Biochim Biophys Acta Protein Struct Mol Enzymol 870:31–40

    Article  CAS  Google Scholar 

  32. Moreira MJA, Ferreira LMGA (2005) Chem Eng Sci 60:5022–5034

    Article  CAS  Google Scholar 

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Acknowledgements

This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIT) (No. 2019R1F1A1062845). S.-W. Han was financially supported by Initiative for Biological Function & Systems under the BK21 PLUS Program of Korean Ministry of Education.

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  1. Sang-Woo Han and Ye-Ri Choi contributed equally to this work.

Authors and Affiliations

  1. Department of Biotechnology, Yonsei University, Engineering Building 2 (Rm 512), 50 Yonsei-Ro, Seodaemun-Gu, Seoul, 03722, South Korea

    Sang-Woo Han, Ye-Ri Choi & Jong-Shik Shin

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  1. Sang-Woo Han
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  2. Ye-Ri Choi
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  3. Jong-Shik Shin
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Correspondence to Jong-Shik Shin.

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Han, SW., Choi, YR. & Shin, JS. Biocatalytic Decarboxylation of Aromatic l-Amino Acids with In Situ Removal of Both Products for Enhanced Production of Biogenic Amines. Catal Lett 151, 2996–3003 (2021). https://doi.org/10.1007/s10562-021-03535-6

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